RIMINOPHENAZINES WITH 2-(HETEROARYL) AMINO SUBSTITUENTS AND THEIR ANTI-MICROBIAL ACTIVITY

Info

Publication number: 20140243327
Type: Application
Filed: May 1, 2014
Publication Date: Aug 28, 2014
Applicant: Global Alliance for TB Drug Development (New York, NY)
Inventors: Kai Liu (Beijing), Christopher B. Cooper (Lawrenceville, NJ), Haihong Huang (Beijing), Chun Li (Beijing), Binna Liu (Beijing), Yang Liu (Beijing), Zhenkun Ma (Westfield, NJ), Jingbin Wang (Beijing), Dali Yin (Beijing), Dongfeng Zhang (Beijing), Gang Zhang (Beijing), Hao Zhang (Beijing)
Application Number: 14/267,183

Abstract

The present invention relates to riminophenazines having heteroaromatic substitutions, including those with 2-heteroaryl-amino substituents, to their preparation, and to their use as drugs for treating Mycobacterium tuberculosis and other microbial infections, either alone or in combination with other anti-infective treatments. A general representation of the 2-(heteroaryl)amino-riminophenazines is shown below.

Description

Description

RELATED APPLICATION

This application claims priority to U.S. Provisional Patent Application No. 61/359,638, filed Jun. 29, 2010, the entire content of which is hereby incorporated by reference.

BACKGROUND

The present invent on relates to riminophenazines having heteroaromatic substitutions, to their preparation, and to their use as drugs for treating Mycobacterium tuberculosis and other microbial infections, either alone or in combination with other anti-infective treatments.

Mycobacterium tuberculosis (“M.tb”) is the causative agent of tuberculosis (“TB”), a devastating infectious disease. It is estimated that about 2 million TB patients die each year globally. There are urgent needs for new drugs to fight the increasing threat of tuberculosis.

Current first-line drug therapy for tuberculosis is long and complex, involving multidrug combinations (usually isoniazid, rifampin, pyrazinamide and ethambutol) given daily for 6 to 9 months. Furthermore, these drugs are relatively ineffective against the resistant form of the disease and difficult to use to treat TB/HIV co-infected patients due to drug-drug interactions (Ma et al., 2009).

Clofazimine was first reported in 1957 by Barry and was found to possess potent antituberculosis activity (Barry, V. C., 1957). It demonstrated in vivo anti-TB activity in mice and hamsters, but failed to show efficacy in guinea pig and monkey models. The major drawbacks of elofazimine are skin discoloration, high fat tissue distribution, and very long half-life (70 days). New riminophenazine analogues have been synthesized to identify compounds with improved activity, lower side effects, and better solubility. Among those compounds, B4154 and B4157 showed improved in vitro activity (V. M. Reddy, 1996).

The structures of clofazimine, B4154, and B4157 are shown below.

One of the major advantages of the riminophenazine class is their low frequency for resistance development. They are highly potent against various forms of drug-resistant TB. New and improved riminophenazines could potentially contribute to the treatment of both drug-susceptible and drug-resistant tuberculosis.

SUMMARY

The current invention pertains to riminophenazines with 2-(heteroaryl)amino substituents, their methods of preparation, and their use as treatments for tuberculosis and other microbial infections.

In the current riminophenazine molecules, the phenylamino group attached to the 2-position of the riminophenazine core can be replaced by a heteroarylamino group as shown in general formula (I) below.

In this structure, R₁, R₂, R₃and R₄can be a variety of substituents. The heteroaromatic ring represents a nitrogen-containing heteroaromatic group. It can be substituted or non-substituted pyridyl wherein X═N and Y═Z═CH, or it can be pyrimidyl wherein X═Y═N and Z═CH, or it can be pyrazinyl wherein X═Z═N and Y═CH. The most preferred compounds include a group of riminophenazines with the 2-phenylamino group replaced by a 2-(3-pyridyl)amino substitution.

The synthesis of riminophenazines of formula (I) follows a modified synthetic procedure reported in U.S. Pat. No. 3,499,899. For example, riminophenazines with 2-(3-pyridyl)amino substitutions can be prepared by the following route: 1,5-Difluoro-2,4-dinitrobenzene (DFDNB) was used to ensure easier substitution of the two fluoro by amines, as shown in FIG. 1. The synthesis is started with 1-fluoro-2-nitrobenzene and anilines. The reaction mixture is then heated at 180-190° C. to give 1-anilino-2-nitrobenzene. After reduction of the nitro group, it is coupled with 1,5-difluoro-2,4-dinitrobenzene and then the second fluoro is replaced by 3-aminopyridines. The two nitro groups are reduced either by Zn/acetic acid or by catalytic hydrogenation over Pd—C. After reduction, the tetra-amino compound (without isolation) is stirred and oxidized by air to form the corresponding riminophenazine. The imino group is further derivatized by different aliphatic and heteroaliphatic amines to give the final products. A general representation of the 2-N-(3-pyridyl)-riminophenazines is shown as general formula (II) below.

In this representation shown as general formula (II), R₁can be H, alkyl, alkoxyl, cycloalkyl, heterocycloalkyl, Cl, F, Br, CF₃, OCH₃, OCF₃, SCH₃, SOCH₃, or a combination of any two or three of them, the same or different. R₃can be H, alkyl, alkoxyl, cycloalkyl, heterocycloalkyl, halo (F, Cl, Br), NAc, or a combination of any two or three of them, the same or different. R₄can be H, halo (Cl, Br, F), alkyl, alkoxyl, or mono-, di-, or cycloalkylamino with or without an additional O, S or NR′ in the ring, where R′ is an alkyl or substituted alkyl group; and R₂be alkyl, cycloalkyl, substituted alkyl or substituted cycloalkyl; cycloalkyl herein could have an additional O, S, or NR′ in the ring, where R′ is as defined above. A “substituted alkyl or cycloalkyl” is defined as alkyl or cycloalkyl substituted by the groups selected from H, alkyl, alkyoxy, halo, or mono-, di- or cycloalkylamino.

The anti-tuberculosis activity of the compounds was tested against H37Rv strains both in vitro and in vivo. In the in vitro assay, most of the compounds in this class showed equal or better activity when compared with clofazimine, rifampicin or isoniazid.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 shows a general synthetic scheme for the synthesis of riminophenazines with 2-(3-pyridyl)-amino substitutions.

DETAILED DESCRIPTION

The current invention pertains to riminophenazines with 2-(heteroaryl)amino substituents, their methods of preparation, and uses of the compounds as treatment for tuberculosis and other microbial infections.

A general representation of the 2-(heteroaryl)amino-riminophenazines is shown as general formula (I) below.

In this structure, R₁, R₂, R₃and R₄can be a variety of substituents. R₁can be a substituent selected from the group consisting of H, alkyl, substituted alkyl, alkoxyl, substituted alkoxyl, monoalkylamino, dialkylamino, cycloalkylamino, substituted cycloalkylamino, halo, CF₃, OCF₃, SCH₃, SOCH₃, and combinations of any two or three of these listed substitutents, wherein the two or three substituents are the same or different. R₃can be a substituent selected from the group consisting of H, alkyl, substituted alkyl, alkoxyl, substituted alkoxyl, monoalkylamino, dialkyl amino, cycloalkylamino, substituted cycloalkylamino, halo, NAc, and combinations of any two or three of these listed substituents, wherein the two or three substituents are the same or different. R₄can be a substituent selected from the group consisting of H, alkyl, substituted alkyl, alkoxyl, substituted alkoxyl, halo, or monoalkylamino, dialkylamino, and cycloalkylamino. The heteroaromatic ring containing X, Y, and Z represents a N-containing heteroaromatic group. It can be substituted or non-substituted pyridyl wherein X═N and Y═Z═CH, pyrimidyl wherein X═Y═N and Z═CH, or pyrazinyl wherein X═Z═N and Y═CH.

Additionally, with regard to R₁, R₃, and R₄, if they are cycloalkylamino rings, they can also include O, S, or NR′ in the ring, wherein R′ is an alkyl or substituted alkyl group. These cycloalkylamino rings can also be further substituted. With regard to R₂, if it is a cycloalkyl ring, then it can also include O, S, or NR′ in the ring, wherein R′ is an alkyl or substituted alkyl group. The cycloalkyl ring can also be further substituted.

The preferred compounds include a group of riminophenazines with 2-phenylamino replaced by a 2-(3-pyridyl)-amino substitution. A general representation of the 2-(3-pyridyl)amino-riminophenazines is shown as general formula (II) below.

In this representation shown as general formula (II), R₁can be H, alkyl, alkoxyl, cycloalkyl, heterocycloalkyl, Cl, F, Br, CF₃, OCH₃, OCF₃, SCH₃, SOCH₃, or a combination of any two or three of them, the same or different. R₃can be H, alkyl, alkoxyl, cycloalkyl, heterocycloalkyl, halo (F, Cl, Br), NAc, or a combination of any two or three of them, the same or different. R₄can be H, halo (Cl, Br, F), alkyl, alkoxyl, or mono-, di-, or cycloalkylamino with or without an additional O, S or NR′ in the ring, where R′ is an alkyl or substituted alkyl group. R₂can be a alkyl, cycloalkyl, substituted alkyl or substituted cycloalkyl. If it is cycloalkyl, it could have an additional O, S, or NR′ in the ring, where R′ is as defined above. A “substituted alkyl or cycloalkyl” is defined as alkyl or cycloalkyl substituted by the groups selected from H, alkyl, alkyoxy, halo, or mono-, di- or cycloalkylamino.

Table 1 below shows a variety of examples of the 2-(3-pyridyl)amino-riminophenazines by indicating the structures shown as general formula (II) present at R₁, R₂, R₃and R₄of the figure above, as well as their in vitro activity against Mycobacterium tuberculosis H37Rv strains, described in Example 2 below.

TABLE 1 MIC (μg/mL) against Compds R₁ R₂ R₃ R₄ H37Rv TBI-054 H H H 0.03 TB-055 H H H 0.5 TBI-056 H H H 0.25 TBI-057 H H H 0.125 TBI-058 H H H 0.06 TBI-059 H H H 0.125 TBI-060 H H H 1.0 TBI-300 4-CH₃ H H 0.03 TBI-301 4-CH₃ H H 0.06 TBI-302 4-CH₃ H H 0.125 TBI-303 4-CH₃ H H 0.03 TBI-304 4-CH₃ H H 0.25 TBI-305 4-CH₃ H H 0.125 TBI-307 4-CH₃ H H 0.125 TBI-416 4-Cl H H 0.03 TBI-427 4-Cl H H 0.125 TBI-428 4-Cl H H 0.25 TBI-433 4-Cl H H 0.25 TBI-434 4-Cl H H 0.03 TBI-435 4-Cl H H 0.25 TBI-436 4-Cl H H 0.03 TBI-437 4-Cl H H 0.125 TBI-422 4-Cl H H 0.06 TBI-458 4-Cl H H 0.018 TBI-679 4-F H H 0.03 TBI-680 4-F H H 0.5 TBI-681 4-F H H 0.06 TBI-682 4-F H H 0.25 TBI-683 4-F H H 0.125 TBI-684 4-F H H 0.5 TBI-685 4-F H H 0.125 TBI-920 4-F H H 0.029 TBI-921 4-F H H 0.434 TBI-922 4-F H H 0.012 TBI-923 4-F H H 0.021 TBI-678 4-CF₃ H H 0.03 TBI-686 4-CF₃ H H 0.125 TBI-687 4-CF₃ H H 0.06 TBI-688 4-CF₃ H H 0.03 TBI-689 4-CF₃ H H 0.125 TBI-690 4-CF₃ H H 0.125 TBI-691 4-CF₃ H H 0.06 TBI-157 4-OCF₃ H H 0.03 TBI-158 4-OCF₃ H H 0.03 TBI-159 4-OCF₃ H H 0.25 TBI-160 4-OCF₃ H H 0.125 TBI-161 4-OCF₃ H H 0.03 TBI-162 4-OCF₃ H H 0.03 TBI-163 4-OCF₃ H H 0.06 TBI-061 H 2′-MeO H 0.06 TBI-062 H 2′-MeO H 0.061 TBI-063 H 2′-MeO H 0.06 TBI-064 H 2′-MeO H 0.057 TBI-065 H 2′-MeO H 0.080 TBI-066 H 2′-MeO H 0.026 TBI-079 H 2′-MeO H 0.068 TBI-087 H 2′-MeO H 0.466 TBI-097 H 2′-MeO H 0.032 TBI-505 H 2′-MeO H 0.043 TBI-073 H 2′-Me H 0.058 TBI-075 H 2′-Me H 0.328 TBI-076 H 2′-Me H 0.042 TBI-077 H 2′-Me H 0.016 TBI-092 H 2′-Me H 0.5 TBI-078 H □Me 2′-Me H 0.019 TBI-067 H 6′-Me H 0.048 TBI-068 H 6′-Me H 0.156 TBI-069 H 6′-Me H 0.219 TBI-072 H 6′-Me H 0.091 TBI-070 H 6′-Me H 0.080 TBI-086 H 6′-Me H 0.5 TBI-095 H 6′-Me H 0.048 TBI-506 H 6′-Me H 0.05 TBI-080 H 6′-Me H 0.243 TBI-081 H 5′-Me H 0.117 TBI-082 H 5′-Me H 0.111 TBI-083 H 5′-Me H 0.049 TBI-084 H 5′-Me H 0.059 TBI-085 H 5′-Me H 0.5 TBI-096 H 5′-Me H 0.069 TBI-510 H 6′-MeO H 0.5 TBI-511 H 6′-MeO H 0.177 TBI-512 H 6′-MeO H 0.41 TBI-513 H 6′-MeO H 0.244 TBI-514 H 6′-MeO H 0.243 TBI-515 H 6′-MeO H 0.233 TBI-088 4-Br H H 0.023 TBI-089 4-Br H H 0.021 TBI-090 4-Br H H 0.016 TBI-091 4-Br H H 0.062 TBI-093 4-Br H H 0.163 TBI-094 4-Br H H 0.5 TBI-098 4-Br H H 0.028 TBI-099 4-Br 6′-Me H 0.049 TBI-100 4-Br 6′-Me H 0.011 TBI-501 4-Br 6′-Me H 0.09 TBI-502 4-Br 6′-Me H 0.217 TBI-503 4-Br 6′-Me H 0.097 TBI-504 4-Br 6′-Me H 0.044 TBI-507 4-Br 2′-Me H 0.062 TBI-508 4-Br 2′-Me H 0.021 TBI-509 4-Br 2′-Me H 0.015 TBI-516 4-Br 2′-MeO H 0.049 TBI-517 4-Br 2′-MeO H 0.029 TBI-308 4-CH₃ 2′-MeO H 0.125 TBI-309 4-CH₃ 2′-MeO H 0.06 TBI-310 4-CH₃ 2′-MeO H 0.03 TBI-311 4-CH₃ 2′-MeO H 0.125 TBI-313 4-CH₃ 2′-MeO H 0.016 TBI-314 4-CH₃ 2′-MeO H 0.024 TBI-312 4-CH₃ 2′-Me H 0.053 TBI-321 4-CH₃ 2′-Me H 0.419 TBI-322 4-CH₃ 2′-Me H 0.092 TBI-323 4-CH₃ 2′-Me H 0.057 TBI-324 4-CH₃ 2′-Me H 0.120 TBI-325 4-CH₃ 2′-Me H 0.056 TBI-326 4-CH₃ 2′-Me H 0.100 TBI-306 4-CH₃ 6′-Me H 0.106 TBI-315 4-CH₃ 6′-Me H 0.057 TBI-316 4-CH₃ 6′-Me H 0.028 TBI-317 4-CH₃ 6′-Me H 0.055 TBI-318 4-CH₃ 6′-Me H 0.087 TBI-319 4-CH₃ 6′-Me H 0.173 TBI-320 4-CH₃ 6′-Me H 0.110 TBI-693 4-F 2′-Me H 0.03 TBI-1012 4-F 2′-Me H 0.026 TBI-1013 4-F 2′-Me H 0.019 TBI-1014 4-F 2′-Me H 0.025 TBI-1015 4-F 2′-Me H 0.387 TBI-1018 4-F 2′-Me H 0.028 TBI-1023 4-F 2′-Me H 0.0075 TBI-1002 4-F 2′-MeO H 0.016 TBI-1003 4-F 2′-MeO H 0.039 TBI-1004 4-F 2′-MeO H 0.038 TBI-1005 4-F 2′-MeO H 0.213 TBI-1008 4-F 2′-MeO H 0.248 TBI-1009 4-F 2′-MeO H 0.03 TBI-1010 4-F 2′-MeO H 0.011 TBI-1016 4-F 2′-MeO H 0.037 TBI-692 4-F 6′-Me H 0.06 TBI-1001 4-F 6′-Me H 0.06 TBI-900 4-F 6′-Me H 0.125 TBI-901 4-F 6′-Me H 0.102 TBI-902 4-F 6′-Me H 0.058 TBI-904 4-F 6′-Me H 0.016 TBI-1017 4-F 6′-Me H 0.056 TBI-905 4-F 6′-Me H 0.057 TBI-906 4-F 6′-Me H 0.5 TBI-907 4-F 6′-Me H 0.063 TBI-908 4-F 6′-Me H 0.03 TBI-90B 4-F 6′-Me H 0.397 TBI-910 4-F 6′-NAc H 0.147 TBI-911 4-F 6′-NAc H 0.360 TBI-912 4-F 6′-NAc H 0.351 TBI-913 4-F 6′-NAc H 0.144 TBI-915 4-F 6′-NAc H 0.211 TBI-916 4-F 6′-NAc H 0.014 TBI-917 4-F 6′-NAc H 1.0 TBI-438 4-Cl 2′-MeO H 0.03 TBI-439 4-Cl 2′-MeO H 0.06 TBI-440 4-Cl 2′-MeO H 0.06 TBI-442 4-Cl 2′-MeO H 0.016 TBI-443 4-Cl 2′-MeO H 0.016 TBI-444 4-Cl 2′-MeO H 0.016 TBI-451 4-Cl 2′-MeO H 0.057 TBI-441 4-Cl 6′-Me H 0.06 TBI-445 4-Cl 6′-Me H 0.076 TBI-446 4-Cl 6′-Me H 0.016 TBI-447 4-Cl 6′-Me H 0.028 TBI-449 4-Cl 6′-Me H 0.030 TBI-450 4-Cl 6′-Me H 0.016 TBI-448 4-Cl 2′-Me H 0.055 TBI-452 4-Cl 2′-Me H 0.168 TBI-453 4-Cl 2′-Me H 0.011 TBI-699 4-CF₃ 2′-MeO H 0.029 TBI-700 4-CF₃ 2′-MeO H 0.016 TBI-701 4-CF₃ 2′-MeO H 0.016 TBI-702 4-CF₃ 2′-MeO H 0.016 TBI-703 4-CF₃ 2′-MeO H 0.020 TBI-704 4-CF₃ 2′-MeO H 0.061 TBI-710 4-CF₃ 2′-MeO H 0.03 TBI-718 4-CF₃ 2′-MeO H 0.015 TBI-719 4-CF₃ 2′-MeO H 0.204 TBI-728 4-CF₃ 2′-MeO H 0.033 TBI-694 4-CF₃ 6′-Me H 0.03 TBI-695 4-CF₃ 6′-Me H 0.016 TBI-696 4-CF₃ 6′-Me H 0.032 TBI-697 4-CF₃ 6′-Me H 0.053 TBI-698 4-CF₃ 6′-Me H 0.108 TBI-716 4-CF₃ 6′-Me H 0.041 TBI-717 4-CF₃ 6′-Me H 0.015 TBI-738 4-CF₃ 6′-Me H 0.029 TBI-164 4-OCF₃ 2′-MeO H 0.028 TBI-165 4-OCF₃ 2′-MeO H 0.016 TBI-166 4-OCF₃ 2′-MeO H 0.016 TBI-167 4-OCF₃ 2′-MeO H 0.016 TBI-168 4-OCF₃ 2′-MeO H 0.109 TBI-169 4-OCF₃ 2′-MeO H 0.060 TBI-359 3,4-dichloro 2′-MeO H 0.099 TBI-361 3,4-dichloro 2′-MeO H 0.08 TBI-362 3,4-dichloro 2′-MeO H 0.059 TBI-363 2,4-dichloro H H 0.03 TBI-1019 3-OCF₃ H H 0.057 TBI-1020 3-OCF₃ H H 0.058 TBI-1021 3-OCF₃ H H 0.054 TBI-1022 3-OCF₃ H H 0.074 TBI-1027 3-OCF₃ H H 0.383 TBI-1024 3-OCF₃ H H 0.112 TBI-1032 3-OCF₃ 2′-Me H 0.107 TBI-1033 3-OCF₃ 2′-Me H 0.242 TBI-1034 3-OCF₃ 2′-Me H 0.059 TBI-1035 3-OCF₃ 2′-Me H 0.062 TBI-1038 3-OCF₃ 2′-MeO H 0.118 TBI-1039 3-OCF₃ 2′-MeO H 0.059 TBI-1040 3-OCF₃ 2′-MeO H 0.086 TBI-1041 3-OCF₃ 2′-MeO H 0.115 TBI-1025 4-F 5′-Me H 0.122 TBI-1026 4-F 5′-Me H 0.121 TBI-1028 4-F 5′-Me H 0.06 TBI-1029 4-F 5′-Me H 0.027 TBI-1030 4-F 5′-Me H 0.012 TBI-1031 4-F 5′-Me H 0.028 TBI-930 4-F 6′-MeO H 0.494 TBI-931 4-F 6′-MeO H 0.238 TBI-932 4-F 6′-MeO H 0.148 TBI-933 4-F 6′-MeO H 0.175 TBI-934 4-F 6′-MeO H 0.3 TBI-935 4-F 6′-MeO H 0.205 TBI-940 4-F 4′-Me H 0.062 TBI-705 4-CF₃ 2′-Me H 0.014 TBI-706 4-CF₃ 2′-Me H 0.011 TBI-707 4-CF₃ 2′-Me H 0.011 TBI-708 4-CF₃ 2′-Me H 0.028 TBI-709 4-CF₃ 2′-Me H 0.108 TBI-729 4-CF₃ 2′-Me H 0.186 TBI-734 4-CF₃ 2′-Me H 0.014 TBI-711 4-CF₃ 6′-NAc H 0.11 TBI-712 4-CF₃ 6′-NAc H 0.158 TBI-713 4-CF₃ 6′-NAc H 0.022 TBI-714 4-CF₃ 6′-NAc H 0.686 TBI-715 4-CF₃ 6′-NAc H 0.06 TBI-721 4-CF₃ 5′-Me H 0.082 TBI-722 4-CF₃ 5′-Me H 0.031 TBI-723 4-CF₃ 5′-Me H 0.041 TBI-724 4-CF₃ 5′-Me H 0.03 TBI-725 4-CF₃ 5′-Me H 0.031 TBI-726 4-CF₃ 5′-Me H 0.058 TBI-727 4-CF₃ 5′-Me H 0.405 TBI-731 4-CF₃ 6′-MeO H 0.348 TBI-732 4-CF₃ 6′-MeO H 0.113 TBI-733 4-CF₃ 6′-MeO H 0.111 TBI-735 4-CF₃ 6′-MeO H 0.186 TBI-736 4-CF₃ 6′-MeO H 0.224 TBI-737 4-CF₃ 6′-MeO H 0.119 TBI-891 2-Cl H H 0.036 TBI-892 2-Cl H H 0.028 TBI-870 2-Cl 2′-MeO H 0.084 TBI-820 3-Cl 2′-MeO H 0.057 TBI-811 3-Cl H H 0.5 TBI-812 3-Cl H H 0.013 TBI-814 3-Cl H H 0.04 TBI-880 4-Cl 5′-Br H 0.036 TBI-881 4-Cl 5′-Br H 0.052 TBI-720 2-CF₃ H H 0.214 TBI-739 2-CF₃ H H 0.239 TBI-730 3-CF₃ H H 0.205 TBI-454 3-CH₃S H H 0.213 TBI-455 3-CH₃SO H H 0.5 TBI-456 4-CH₃S H H 0.05 TBI-457 4-CH₃SO H H 0.469 TBI-327 4-CH₃ 5′-CH₃ H 0.109 TBI-328 4-CH₃ 5′-CH₃ H 0.037 TBI-329 4-CH₃ 5′-CH₃ H 0.092 TBI-330 4-CH₃ 5′-CH₃ H 0.035 TBI-331 4-CH₃ 2′-MeO H 0.047 TBI-332 4-CH₃ 2′-MeO H 0.294 TBI-333 4-CH₃ H H 0.061 TBI-334 4-CH₃ 6′-CH₃ H 0.372 TBI-335 4-CH₃ 2′-CH₃ H 0.336 TBI-336 3,4-dichloro H H 0.055 TBI-337 4-CH₃ 5′-CH₃ H 0.452 TBI-338 4-CH₃ H H 0.5 TBI-339 4-CH₃ 2′-MeO H 0.033 TBI-340 4-CH₃ 6′-CH₃ H 0.149 TBI-341 4-CH₃ 2′-CH₃ H 0.014 TBI-342 4-CH₃ 5′-CH₃ H 0.022 TBI-343 3,4-dichloro H H 0.014 TBI-344 4-CH₃ 2′-MeO H 0.04 TBI-345 4-CH₃ H H 0.221 TBI-346 4-CH₃ 6′-CH₃ H 0.058 TBI-347 4-CH₃ 2′-CH₃ H 0.042 TBI-348 4-CH₃ 5′-CH₃ H 0.118 TBI-349 4-CH₃ H H 0.0075 TBI-350 3,4-dichloro H H 0.031 TBI-351 3,4-dichloro H H 0.079 TBI-352 3,4-dichloro H H 0.096 TBI-353 3,4-dichloro 6′-CH₃ H 0.025 TBI-354 3,4-dichloro 6′-CH₃ H 0.229 TBI-355 3,4-dichloro 6′-CH₃ H 0.09 TBI-356 4-CH₃ 6′-MeO H 0.459 TBI-357 4-CH₃ 6′-MeO H 0.228 TBI-358 4-CH₃ 6′-MeO H 0.202 TBI-360 4-CH₃ 6′-MeO H 0.2 TBI-364 4-OCF₃ 2′-MeO H 0.015 TBI-365 4-OCF₃ 2′-MeO H 0.018 TBI-366 3,4-dichloro 2′-MeO H 0.025 TBI-367 2,4-dichloro H H 0.023 TBI-368 2,4-dichloro H H 0.054 TBI-369 2,4-dichloro 2′-MeO H 0.104 TBI-370 2,4-dichloro 2′-MeO H 0.052 TBI-371 2,4-dichloro 2′-MeO H 0.044 TBI-372 4-OCF₃ 2′-MeO H 0.098 TBI-373 4-CH₃ 2′-MeO H 0.125 TBI-374 4-CH₃ 6′-CH₃ H 0.125 TBI-375 3,4-dichloro 2′-MeO H 0.125 TBI-518 4-Br 2′-MeO H 0.02 TBI-519 4-Br 2′-MeO H 0.015 TBI-520 4-Br 2′-MeO H 0.043 TBI-521 4-Br 2′-MeO H 0.031 TBI-522 3-F H H 0.062 TBI-523 3-F 2′-MeO H 0.06 TBI-524 3-F 2′-MeO H 0.061 TBI-525 3,4-difluoro H H 0.058 TBI-526 3,4-difluoro H H 0.079 TBI-527 3,4-difluoro H H 0.039 TBI-528 3,4-difluoro H H 0.216 TBI-529 3,4-difluoro 2′-MeO H 0.066 TBI-530 3,4-difluoro 2′-MeO H 0.04 TBI-531 3,4-difluoro 2′-MeO H 0.03 TBI-532 3,4-difluoro 2′-MeO H 0.067 TBI-1042 4-F 2′-MeO H 0.034 TBI-1043 4-F 2′-CH₃ H 0.021 TBI-1044 2-OCF₃ 2′-MeO H 0.25 TBI-1045 2-OCF₃ 2′-MeO H 0.4 TBI-1046 2-OCF₃ 2′-MeO H 0.44 TBI-1047 2-OCF₃ 2′-MeO H 0.465 TBI-1048 4-F 2′-MeO H 0.226 TBI-1049 4-F 2′-MeO H 0.162 TBI-744 4-CF₃ 2′-MeO H 0.059 TBI-825 3-Cl 2′-MeO H 0.125 TBI-871 4-Cl 2′-MeO H 0.03 TBI-80C 3-Cl 6′-CH₃ H 0.327 TBI-826 3-Cl 2′-MeO H 0.125 TBI-872 4-Cl 2′-MeO H 0.06 TBI-810 3-Cl H H 0.103 TBI-890 2-Cl H H 0.476 TBI-882 4-Cl 5′-Br H 0.015 TBI-883 4-Cl 5′-Br H 0.03 TBI-821 3-Cl 2′-MeO H 0.25 TBI-822 3-Cl 2′-MeO H 0.125 TBI-823 3-Cl 2′-MeO H 0.03 TBI-824 3-Cl 2′-MeO H 0.06 TBI-80A 3-Cl 6′-CH₃ H 0.125 TBI-80B 3-Cl 6′-CH₃ H 0.125 TBI-950 4-OCF₃ 6′-CH₃ H 0.035 TBI-741 4-Cl 2′-MeO 7-F 0.035 TBI-914 4-Cl 6′-Me 7-F >0.5 TBI-918 4-Cl 6′-Me 7-F 0.253 TBI-925 4-Cl 6′-Me 7-F 0.078 TBI-924 4-Cl 2′-MeO 7-F 0.06 TBI-926 4-Cl 2′-MeO 7-F 0.103 TBI-927 4-Cl 2′-MeO 7-F 0.04 TBI-928 4-Cl 2′-MeO 7-F 0.5 TBI-938 4-Cl 6′-Me 8-F 0.125 TBI-943 4-Cl 6′-Me 8-F 0.06 TBI-929 4-Cl 2′-MeO 8-F 0.125 TBI-936 4-Cl 2′-MeO 8-F 0.06 TBI-937 4-Cl 2′-MeO 8-F 0.125 TBI-939 4-Cl 2′-MeO 7-MeO 0.125 TBI-941 4-Cl 2′-MeO 7-MeO 0.06 TBI-942 4-Cl 2′-MeO 7-MeO 0.125 TBI-894 4-Cl 2′-MeO 7-MeO 0.06 TBI-895 4-Cl 2′-MeO 7-MeO 0.125 TBI-944 3,4-dichloro 6′-Me H 0.06 TBI-945 3,4-dichloro 6′-Me H 0.25 TBI-948 3,4-dichloro 6′-Me H 0.125 TBI-946 3,4-dichloro 2′-MeO H 0.06 TBI-947 2,4-dichloro 2′-MeO H 0.06 TBI-893 2,4-dichloro 2′-MeO H 0.06 TBI-949 3,4-dichloro 6′-Me 7-F 0.816 TBI-896 3,4-dichloro 6′-Me 7-F 0.25 TBI-897 3,4-dichloro 6′-Me 7-F 0.25 TBI-899 3,4-dichloro 2′-MeO 7-F 0.125 TBI-884 3,4-dichloro 2′-MeO 7-F 0.5 TBI-885 3,4-dichloro 2′-MeO 7-F 0.06 TBI-886 3,4-dichloro 2′-MeO 8-F 0.06 TBI-887 3,4-dichloro 6′-Me 8-F 0.062 TBI-888 3,4-dichloro 6′-Me 8-F 0.028 TBI-873 3,4-dichloro 6′-Me 8-F 0.076 TBI-878 3,4-dichloro 6′-Me 8-F 0.029 TBI-874 3,4-dichloro 2′-MeO 8-F 0.129 TBI-875 3,4-dichloro 2′-MeO 8-F 0.047 TBI-877 3,4-dichloro 2′-MeO 8-F 0.091 TBI-879 3,4-dichloro 2′-MeO 8-F 0.109 TBI-861 4-OCF₃ 2′-MeO 8-F 0.058 TBI-862 4-OCF₃ 2′-MeO 8-F 0.088 TBI-863 4-OCF₃ 6′-Me 8-F 0.061 TBI-864 4-OCF₃ 6′-Me 8-F 0.057 TBI-865 4-OCF₃ 6′-Me 8-F 0.031 TBI-866 4-OCF₃ 6′-Me 8-F 0.027 TBI-898 4-Cl 6′-Me 8-MeO 0.25 TBI-859 4-Cl 2′-MeO 8-F 0.015 TBI-867 4-Cl 6′-Me 8-MeO 0.058 TBI-868 4-Cl 6′-Me 7-MeO 0.028 TBI-869 4-Cl 6′-Me 7-MeO 0.056 TBI-858 4-OCF₃ 2′-MeO 7-F 0.08 TBI-857 4-OCF₃ 2′-MeO 7-F 0.045 TBI-856 4-OCF₃ 2′-MeO 7-F 0.029 TBI-855 4-OCF₃ 2′-MeO 7-F 0.193 TBI-854 4-OCF₃ 6′-Me 7-F 0.067 TBI-853 4-OCF₃ 6′-Me 7-F 0.025 TBI-852 4-OCF₃ 6′-Me 7-F 0.024 TBI-1220 4-NHAc 2′-MeO H >0.5 TBI-1221 4-NHAc 2′-MeO H 0.900 TBI-1222 4-NHAc 2′-MeO H 0.925 TBI-1223 4-NHAc 2′-MeO H 1.488 TBI-1224 4-NHAc 6′-Me H TBD TBI-1225 4-NHAc 2′-MeO H TBD TBI-1227 4-NHAc 2′-MeO H TBD TBI-1228 4-NHAc 6′-Me H 2.398 TBI-1229 4-NHAc 6′-Me H 0.482 TBI-1230 4-NHAc 6′-Me H TBD TBI-1231 4-NHAc 6′-Me H TBD TBI-1236 4-COOCH₃ 2′-MeO H TBD TBI-1237 4-COOCH₃ 2′-MeO H TBD TBI-1426 3,4-difluoro 2′-MeO H 0.014 TBI-1427 3,4-difluoro 2′-MeO H 0.056 TBI-1428 3,4-difluoro 2′-MeO H 0.054 TBI-1429 3,4-difluoro H H 0.011 TBI-1430 3,4-difluoro H H 0.059 TBI-1432 3,4-difluoro H H 0.088 TBI-1064 4-F 2′-MeO 8-CN 0.24 TBI-1065 4-F 2′-MeO 8-CN >16 TBI-1066 4-F 2′-MeO 8-CN >6.639 TBI-1067 4-F 6′-Me 8-CN 0.117 TBI-1068 4-F 6′-Me 8-CN 0.165 TBI-1092 4-F 2′-MeO, 6′-Me H 0.424

Table 2 below shows a variety of examples of the 2-(heteroaryl)amino-riminophenazines shown as general formula (I) by indicating the structures present at R1, R2, R3, R4, X, Y and Z of the figure above, as well as their in vitro activity against Mycobacterium tuberculosis H37Rv strains, described in Example 2 below. In these examples, R₄is H.

TABLE 2 Compds R₁ R₂ R₃ MIC (μg/mL) against H37Rv TBI-952 4-OCF₃ H 0.093 TBI-954 4-OCF₃ 3′-NO₂ 0.030 TBI-1050 4-Cl 3′-NO₂ 0.025 TBI-951 4-OCF₃ H 0.019 TBI-830 4-OCF₃ H 0.014 TBI-860 4-Cl H 0.029 TBI-960 4-Cl H 0.03 TBI-961 4-Cl H 0.015 TBI-980 3-Cl H 0.06 TBI-953 4-OCF₃ H 0.015 TBI-1051 4-Cl H 0.015 TBI-1052 4-F 3′-NO₂ 0.022 TBI-1053 4-F H 0.015 TBI-1054 4-F H 0.446 TBI-1055 4-F H 0.022 TBI-1057 4-F 3′-CN 0.015 TBI-1075 4-Cl 3′-CN 0.016 TBI-1076 4-Cl H 0.014 TBI-1077 4-Cl H <0.0075 TBI-1078 4-F H 0.028 TBI-1079 4-F H 0.037 TBI-1080 4-F H 0.029 TBI-1082 4-F 3′-CN 0.029 TBI-1083 4-F 3′-NO₂ 5.814 TBI-1084 4-F H 0.043 TBI-1085 4-F H 0.038 TBI-1086 4-F 3′-CN 0.04 TBI-1087 4-F H 0.028 TBI-1088 4-F 3′-NO₂ 0.028 TBI-1090 4-Cl H <0.0075 TBI-1091 4-Cl H 0.018 TBI-1433 3,4- difluoro H 0.086 TBI-1436 3,4- difluoro H 0.028 TBI-1437 3,4- difluoro H 0.02 TBI-1438 3,4- difluoro 3′-CN 0.053 TBI-1444 3,4- difluoro 5′-NO₂ 0.114 TBI-1445 3,4- difluoro H 0.056 TBI-1446 3,4- difluoro H 0.03

The riminophenazines with 2-(heteroaryl)amino substituents may occur in different geometric and enantiomeric forms, and both pure forms and mixtures of these separate isomers are included in the scope of this invention, as well as any physiologically functional or pharmacologically acceptable salt derivatives or prodrugs thereof. Production of these alternate forms would be well within the capabilities of one skilled in the art.

The current invention also pertains to methods of prevention or therapy for microbial infections, such as Mycobacterium tuberculosis, including the step of administering a riminophenazine with 2-(heteroaryl)amino substituents.

In another aspect of the present invention there is provided a pharmaceutical composition including a therapeutically effective amount of a riminophenazine with 2-(heteroaryl)amino substituents as defined above and a pharmaceutically acceptable excipient, adjuvant, carrier, buffer or stabiliser. A “therapeutically effective amount” is to be understood as an amount of a riminophenazine with 2-(heteroaryl)amino substituents that is sufficient to show antibacterial or antimicrobial effects. The actual amount, rate and time-course of administration will depend on the nature and severity of the disease being treated. Prescription of treatment is within the responsibility of general practitioners and other medical doctors. The pharmaceutically acceptable excipient, adjuvant, carrier, buffer or stabiliser should be non-toxic and should no interfere with the efficacy of the active ingredient. The precise nature of the carrier or other material will depend on the route of administration, which may be oral, or by injection, such as cutaneous, subcutaneous, or intravenous injection, or by dry powder inhaler.

Pharmaceutical compositions for oral administration may be in tablet, capsule, powder or liquid form, A tablet may comprise a solid carrier or an adjuvant. Liquid pharmaceutical compositions generally comprise a liquid carrier such as water, petroleum, animal or vegetable oils, mineral oil or synthetic oil. Physiological saline solution, dextrose or other saccharide solution or glycols such as ethylene glycol, propylene glycol or polyethylene glycol may be included. A capsule may comprise a solid carrier such as gelatin. For intravenous, cutaneous or subcutaneous injection, the active ingredient will be in the form of a parenterally acceptable aqueous solution which is pyrogen-free and has a suitable pH, isotonicity and stability. Those of relevant skill in the art are well able to prepare suitable solutions using, for example, isotonic vehicles such as sodium chloride solution, Ringer's solution, or lactated Ringer's solution. Preservatives, stabilisers, buffers, antioxidants and/or other additives may be included as required.

The pharmaceutical composition can further comprise one or more additional anti-infective treatments. These anti-infective treatments can be any suitable treatment available commercially or from other sources that are known to effectively prevent or treat microbial infections, such as Mycobacterium tuberculosis.

In another aspect, there is provided the use in the manufacture of a medicament of a therapeutically effective amount of a riminophenazine with 2-(heteroaryl)amino substituents as defined above for administration to a subject. There is also provided a method of making riminophenazines with 2-(heteroaryl)amino substituents.

The term “pharmacologically acceptable salt” used throughout the specification is to be taken as meaning any acid or base derived salt formed from hydrochloric, sulfuric, phosphoric, acetic, citric, oxalic, malonic, salicylic, malic, fumaric, succinic, ascorbic, maleic, methanesulfonic, isoethonic acids and the like, and potassium carbonate, sodium or potassium hydroxide, ammonia, triethylamine, triethanolamine and the like.

The term “prodrug” means a pharmacological substance that is administered in an inactive, or significantly less active, form, Once administered, the prodrug is metabolised in vivo into an active metabolite.

The term “therapeutically effective amount” means a nontoxic but sufficient amount of the drug to provide the desired therapeutic effect. The amount that is “effective” will vary from subject to subject, depending on the age and general condition of the individual, the particular concentration and composition being administered, and the like. Thus, it is not always possible to specify an exact effective amount. However, an appropriate effective amount in any individual case may be determined by one of ordinary skill in the art using routine experimentation. Furthermore, the effective amount is the concentration that is within a range sufficient to permit ready application of the formulation so as to deliver an amount of the drug that is within a therapeutically effective range.

Some preferred examples of the riminophenazines with 2-(3-pyridyl)amino substituents include compounds having the following structures:

Further aspects of the present invention will become apparent from the following description given by way of example only and with reference to the accompanying synthetic schemes.

Example 1 General Synthetic Methods

General procedures for the preparation of 5-(4-chlorophenyl)-3-(1-methylethyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine (TBI-416), or the current riminophenazine compounds, are provided below.

Step A: 2-(4-chloroanilino)-nitrobenzene. A mixture of 2-fluoro-nitrobenzene (33.7 g), 4-chloroaniline (61.0 g) and anhydrous potassium fluoride (13.9 g) was stirred at 180° C. for 10 h. After being cooled to rt, 3 M HCl was added and the mixture was stirred at 100° C. for 30 min. Then cooled to rt, filtered by suction, washed with water to give a brown solid. The solid was dissolved in CH₂Cl₂and filtered through a thin pad of silica gel, washed with CH₂Cl₂. The filtrate was concentrated to dryness, and the residue was recrystallized with 95% ethanol to give 57.0 g of orange solid.

Step B: 2-(4-chloroanilino)-aniline. To a solution of 2-(4-chloroanilino)-nitrobenzene (57.0 g) in CH₂Cl₂(40 mL) was added AcOH (90 mL), then Zn (105 g) was added in small portions. After Zn was added, the color of the mixture became light green, filtered by suction, washed with CH₂Cl₂. The filtrate was concentrated to dryness. Water was added, filtered, and washed with water to give a brown solid. This solid was used directly in the next step without further purification.

Step C: 1-[2-(4-chloroanilino)anilino]-3-fluoro-4,6-dinitrobenzene. The solid from step B was added to a solution of 1,3-difluoro-4,6-dinitrobenzene (46 g) in methanol (200 mL), then triethylamine (31.4 mL) was added, and stirred at rt for 4 h. The reaction mixture was filtered, and the cake was washed with methanol to give 80.6 g of red solid.

Step D: 1-[2-(4-chloroanilino)anilino]-3-(3-pyridyl)amino-4,6-dinitrobenzene, shown below.

A mixture of 1-[2-(4-chloroanilino)anilino]-3-fluoro-4,6-dinitrobenzene (40.3 g), 3-aminopyridine (14.12 g), triethylamine (14 mL) and THF (200 mL) was heated to reflux for 28 h, then about 150 of mL was distilled out. To the residue was added CH₂Cl₂, the solid was filtered, and washed with CH₂Cl₂to give 31.2 g of red solid. ¹H NMR (300 MHz, DMSO-d₆) δ: 9.72 (s, 1H), 9.50 (s, 1H), 9.00 (s, 1H), 8.40-8.37 (m, 2H), 7.77 (s, 1H), 7.63-7.59 (m, 1H), 7.37-7.33 (m, 1H), 7.21-7.09 (m, 5H), 6.92-6.83 (m, 1H), 6.82-6.78 (m, 2H), 5.92 (s, 1H); ESI-MS (m/z): 477 (M+H⁺).

Step E: 5-(4-chlorophenyl)-3-imino-2-(3-pyridyl)amino-3,5-dihydrophenazine, shown below.

Method A. To a suspension of 1-[2-(4-chloroanilino)anilino]-3-(3-pyridyl)amino-4,6-dinitrobenzene (28.6 g) in AcOH (150 mL) was added Zn powder (69 g) in small portions. After Zn was added, the color of the mixture became light green. The mixture was filtered, washed with AcOH and methanol. The filtrate was concentrated to dryness, water and ammonia was added. After being filtered, the cake was washed with water to give a dark solid. The solid was dissolved in methanol and CH₂Cl₂, stirred at rt in contact with air overnight. The solution was concentrated to a small volume, and filtered, washed with methanol to give 23.1 g of dark solid. ¹H NMR (300 MHz, CDCl₃) δ: 8.63 (d, J=2.7 Hz, 1H), 8.37 (dd, J=4.8 Hz, 1.2 Hz, 1H), 7.81-7.70 (m, 4H), 7.34-7.28 (m, 3H), 7.24-7.18 (m, 2H), 6.94 (s, 1H), 6.54-6.51 (m, 1H), 5.23 (s, 1H).
Method B. 9.49 g (21 mmol) of 1-[2-(4-chloroanilino)anilino]-3-(3-pyridyl)amino-4,6-dinitrobenzene was suspended in 100 ml of anhydrous methanol. The mixture was hydrogenation with 0.97 g of 10% Pd—C at 45 psi. Then the Pd—C was removed by filtration. The filtrate was opened in the air and stirred at r.t. over night. The solid separated was filtered out to give the title compound 4.83 g.

Step F: 5-(4-chlorophenyl)-3-(1-methylethyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine, shown below.

To a sealed bomb was added 5-(4-chlorophenyl)-3-imino-2-(3-pyridyl)amino-3,5-dihydrophenazine (23.1 g), isopropylamine (99.4 mL) and dioxane (120 mL). The mixture was stirred at 110° C. in the bomb for 7 h. After being cooled to rt, water was added, suction filtered, washed with water to give a dark solid. The solid was purified by flash column chromatography (EtOAc/hexane 1:2) to give 11.2 g of red solid. mp: 194-196° C., ¹H NMR (300 MHz, DMSO-d₆) δ: 8.63 (brs, 1H), 8.61 (d, J=2.4 Hz, 1H), 8.32 (dd, J=4.8 Hz, 1.2 Hz, 1H), 7.90-7.84 (m, 3H), 7.65-7.58 (m, 3H), 7.25-7.18 (m, 2H), 6.66 (s, 1H), 6.47-6.44 (m, 1H), 5.76 (s, 1H), 3.43-3.35 (m, 1H), 1.06 (d, J=6.3 Hz, 6H). ¹³C NMR (100 MHz, DMSO-d₆) δ: 150.2, 149.9, 144.1, 143.8, 143.5, 136.8, 135.8, 135.3, 134.4, 131.6, 131.1, 130.9, 128.3, 128.0, 127.8, 123.9, 122.9, 114.1, 98.8, 88.3, 48.9, 23.3, HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₆H₂₃ClN₅: 440.1641; found: 440.1643.

General procedures for the preparation of 5-(4-chlorophenyl)-3-(1-methylethyl)imino-2-(pyrimidin-2-yl)amino-3,5-dihydrophenazine (TBI-1051), or the current riminophenazine compounds, are provided below.

Step A: 2-(4-chloroanilino)-nitrobenzene. A mixture of 2-fluoro-nitrobenzene (33.7 g), 4-chloroaniline (61.0 g) and anhydrous potassium fluoride (13.9 g) was stirred at 180° C. for 10 h. After being cooled to rt, 3 M HCl was added and the mixture was stirred at 100° C. for 30 min. Then cooled to rt, filtered by suction, washed with water to give a brown solid. The solid was dissolved in CH₂Cl₂and filtered through a thin pad of silica gel, washed with CH₂Cl₂. The filtrate was concentrated to dryness, and the residue was recrystallized with 95% ethanol to give 57.0 g of orange solid.

Step B: 2-(4-chloroanilino)-aniline. To a solution of 2-(4-chloroanilino)-nitrobenzene (57.0 g) in CH₂Cl₂(40 mL) was added AcOH (90 mL), then Zn powder (105 g) was added in small portions. After Zn powder was added, the color of the mixture became light green, filtered by suction, washed with CH₂Cl₂. The filtrate was concentrated to dryness. Water was added, filtered, and washed with water to give a brown solid. This solid was used directly in the next step without further purification.

Step C: 1-[2-(4-chloroanilino)-anilino]-3-fluoro-4,6-dinitrobenzene. The solid from step B was added to a solution of 1,3-difluoro-4,6-dinitrobenzene (46 g) in methanol (200 mL), then triethylamine (31.4 mL) was added, and stirred at rt for 4 h. The reaction mixture was filtered, and the cake was washed with methanol to give 80.6 g of red solid.

Step D: 1-[2-(4-chloroanilino)-anilino]-3-amino-4,6-dinitrobenzene, shown below.

A mixture of 1-[2-(4-chloroanilino)-anilino]-3-fluoro-4,6-dinitrobenzene (40.3 g), ammonia (50 ml) and THF (80 mL) was heated to 80□ for 12 h in a sealed bomb, then about 70 mL of THF was distilled out. The suspension was filtered by suction, and the filter cake was washed with CH₂Cl₂to give 37.6 g of yellow solid. ¹H NMR (300 MHz, DMSO-d₆) δ: 8.92 (1H, s), 7.77 (3H, m), 7.28 (5H, m), 7.06 (1H, m), 7.00 (2H, m), 6.15 (1H, s), 5.76 (1H, s).

Step E: 5-(4-chlorophenyl)-3-imino-2-amino-3,5-dihydrophenazine, shown below.

Method A: To a suspension of 1-[2-(4-chloroanilino)-anilino]-3-amino-4,6-dinitrobenzene (24.0 g) in AcOH (150 mL) was added Zn powder (69.0 g) in small portions. After Zn powder was added, the color of the mixture became green. The mixture was filtered, washed with AcOH and methanol. The filtrate was concentrated to dryness, water and ammonia was added. After being filtered, the cake was washed with water to give a dark solid. The solid was dissolved in methanol and CH₂Cl₂, stirred at rt in contact with air overnight. The solution was concentrated to a small volume, and filtered, washed with methanol to give 16.9 g of dark solid. ¹H NMR (300 MHz, DMSO-d₆) δ: 7.86 (2H, d, J=8.7 Hz), 7.76 (1H, m), 7.59 (2H, d, J=8.7 Hz), 7.31 (2H, m), 6.78 (2H, br s), 6.57 (1H, m), 6.49 (1H, s), 5.45 (1H, s).
Method B: 8.40 g (21 mmol) of 1-[2-(4-chloroanilino)-anilino]-3-amino-4,6-dinitrobenzene was suspended in 100 mL of anhydrous methanol. The mixture was hydrogenation with 0.97 g of 10% Pd—C at 45 psi. Then the Pd—C was removed by filtration. The filtrate was stirred at rt in contact with air overnight. The solid separated was filtered out to give the title compound 3.90 g.

Step F: 5-(4-chlorophenyl)-3-(1-methylethyl)imino-2-amino-3,5-dihydrophenazine, shown below.

To a sealed bomb was added 5-(4-chlorophenyl-3-imino-2-amino-3,5-dihydro-phenazine (18.6 g), isopropylamine (99.4 mL) and dioxane (120 mL). The mixture was stirred at 110° C. in the bomb for 24 h. After being cooled to rt, water was added, suction filtered, washed with water to give a dark solid. The solid was purified by flash column chromatography (EtOAc/hexane 1:2) to give 5.6 g of red solid. ¹H NMR (300 MHz, DMSO-d₆) δ: 7.84 (2H, d, J=8.4 Hz), 7.59 (1H, m), 7.55 (2H, d, J=8.4 Hz), 7.14 (2H, m), 6.39 (3H, m), 6.27 (1H, s), 5.11 (1H, s), 3.29 (1H, m), 0.98 (6H, d, J=6.3 Hz).

Step G: 5-(4-Chlorophenyl)-3-(1-methylethyl)imino-2-(pyrimidin-2-yl)amino-3,5-dihydrophenazine, shown below.

Under an atmosphere of N₂, toluene (50 mL), 2-bromopyrimidine (4.7 g), 5-(4-chlorophenyl)-3-(1-methylethyl)imino-2-amino-3,5-dihydrophenazine (7.2 g), Pd₂(dba)₃(0.4 g), DPPF (0.9 g) and Cs₂CO₃(9.8 g) were added in turn to a two-necked round-bottomed flask with a reflux condenser. The mixture was refluxed for 2 h, allowed to cool, and filtered. After filtration, the filtrate was concentrated under reduced pressure and the residue was purified by flash silica gel chromatography (EtOAc/hexane 1:2) to give 8.4 g of red solid. mp: 232-235 E, ¹H NMR (300 MHz, CDCl₃) δ: 9.76 (1H, br s), 8.56 (2H, d, J=4.5 Hz), 8.49 (s, 1H), 7.77 (1H, d, J=6.9 Hz), 7.71 (2H, m), 7.32 (2H, m), 7.17 (2H, m), 6.83 (1H, m), 6.44 (1H, d, J=6.9 Hz), 528 (1H, s), 3.47 (1H, m), 1.10 (6H, d, J=6.0 Hz). ¹³C NMR (100 MHz, CDCl₃) δ: 159.3, 157.9, 151.8, 150.1, 140.2, 136.0, 135.7, 135.0, 132.0, 131.7, 130.5, 128.8, 128.3, 122.8, 113.7, 113.5, 108.4, 89.0, 49.4, 23.6. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₁₅H₂₂ClN₆: 441.1589; found: 441.1589.

Example 2 In Vitro Assay for Antimicrobal Susceptibility

Antimicrobial susceptibility testing was performed in 96-well microplates. Initial drug dilutions (6.4 mg/ml) were prepared in dimethyl sulfoxide, and subsequent two-fold dilutions were performed in 0.1 ml of 7H9 in the microplates. The final drug concentrations were about 0.008 μg/ml. Every concentration of test compounds was added to two wells. Control wells consisted of bacteria and positive drug (Clofazimine). Plates were incubated at 37° C. The final bacterial titers were 1×10⁶CFU/ml for H₃₇Rv. Starting at day 7 of incubation, 20 μl of 10× Alamar blue solution and 12.5 μl of 20% Tween 80 were added to each well and the plates were reincubated at 37° C. Wells were observed at 24 h and the colors of all were recorded. Visual MICs were defined as the lowest of drug that prevented a color change from blue to pink. Fluorescence was measured in a microplate fluorometer in bottom-reading mode with excitation at 530 nm and emission at 590 nm, For fluorometric MICs, the lowest drug concentration effecting an inhibition of ≧90% was considered the MIC. The results are shown Table 1 and 2 above.

Example 3 In Vivo Testing

Male BALB/c mice (18˜20 g) were infected intravenously with 0.2 ml portions containing 1×10⁵CFU of H₃₇Rv. One day after the infection, four mice were sacrificed and the numbers of CFU in the spleens and lungs were determined. Organs were removed and homogenized in Middlebrook 7H9 broth. To enumerate CFU, appropriate dilutions of the homogenates were plated onto Middlebrook 7H10 agar and colonies were counted after 3 to 4 weeks of incubation at 37° C. The remaining mice were allocated either to untreated groups or to various drug treated groups (six mice per group). The dose of every test compound was 20 mg/kg. The positive control groups were treated by isoniazid and clofazimine. The test compounds and clofazimine were administered by gavage 5 times weekly. Untreated mice were administered by gavage with CMC. Thirty days postinfection, both untreated and treated mice were sacrificed and lung tissue CFU counts were determined. The significance of the CFU count and organ weight difference was assessed by a two-tailed Student t test. P≦0.01 was considered significant. The results of twelve exemplary compounds are shown Table 3 below.

TABLE 3 TBI- TBI- TBI- TBI- TBI- TBI- Compound 1002 1004 1010 166 416 443 Untreated 8.53 8.53 8.53 8.53 8.53 8.53 Control Log CFU 6.33 6.33 6.33 6.33 6.33 6.33 (CLF- treated) Log CFU 2.20 2.20 2.20 2.20 2.20 2.20 Reduction (CLF) Log CFU 4.85 4.28 4.86 4.66 3.83 5.13 (TBI treated) Log CFU 3.68 4.25 3.67 3.87 4.70 3.40 Reduction (TBI treated) Fold X CLF 1.48 2.05 1.47 1.67 2.50 1.20 (log) Fold X CLF 30.2 112.2 29.5 46.8 316.2 15.8 TBI- TBI- TBI- TBI- TBI- TBI- Compound 444 449 450 678 688 161 Untreated 8.53 8.53 8.53 8.82 8.82 8.82 Control Log CFU 6.33 6.33 6.33 5.99 5.99 5.99 (CLF- treated) Log CFU 2.20 2.20 2.20 2.83 2.83 2.83 Reduction (CLF) Log CFU 4.71 3.87 3.64 5.82 5.99 6.05 (TBI treated) Log CFU 3.82 4.66 4.89 3.00 2.83 2.77 Reduction (TBI treated) Fold X CLF 1.62 2.46 2.69 0.17 0.00 −0.06 (log) Fold XCLF 41.7 288.4 489.8 1.5 1.0 0.9

Example 5 Compounds Synthesized According to General Methods TBI-054, 5-Phenyl-3-(1-methylethyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.06-1.08 (6H, d, J=6.0 Hz, CH(CH₃)₂), 3.38-3.46 (1H, m, J=6.0 Hz, CH(CH₃)₂), 5.28 (1H, s, CH—C═N), 6.48-6.50 (1H, d, J=7.5 Hz, PhH₆), 6.85 (1H, s, CH═C—NH), 7.10-7.19 (2H, m, PhH_7,8), 7.29-7.35 (3H, m, PhH₉. Ph′H_2,6), 7.62-7.80 (5H, m, Ph′H_3,4,5, PyH₆, PyH₅), 8.32-8.33 (1H, d, J=3.9 Hz, PyH₄), 8.59 (1H, d, J=2.4 Hz, PyH₂). ¹³C NMR (100 MHz, CDCl₃) δ: 23.49, 49.28, 89.08, 99.40, 114.16, 122.78, 123.60, 127.64, 127.82, 128.18, 128.79, 129.72, 131.25, 131.74, 135.08, 135.64, 136.96, 137.59, 143.66, 143.92, 144.15, 150.57, 150.96. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₆H₂₄N₅: 406.2031; found: 406.2041.

TBI-055, 5-Phenyl-3-(N-methyl-4-piperidyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.66 (4H, brs, (CH₂CH₂N)₂), 1.96-2.04 (2H, m, CH₂CH₂N), 2.27 (3H, s, CH₃), 2.75-2.79 (2H, m, CH₂CH₂N), 3.06-3.10 (1H, m, NCHCH₂CH₂N), 5.24 (1H, s, CH—C═N), 6.52-6.54 (1H, d, J=7.8 Hz, PhH₆), 6.87 (1H, s, CH—C—NH), 7.12-7.21 (2H, m, PhH₇, s), 7.27-7.34 (3H, m, PhH₉, Ph′H_2,6), 7.64-7.80 (5H, m, PyH₆, PyH₅), 8.32-8.34 (1H, d, J=4.8 Hz, PyH₄), 8.58 (1H, d, J=1.8 Hz, PyH₂). ¹³C NMR (100 MHz, CDCl₃) δ: 32.64, 46.38, 54.05, 89.13, 99.51, 114.23, 122.93, 123.64, 127.89, 128.29, 128.69, 129.76, 131.25, 131.60, 135.09, 135.68, 136.80, 137.51, 143.53, 143.96, 144.29, 150.81, 151.25, HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₉N₆: 461.2453; found: 461.2436.

TBI-056, 5-Phenyl-3-(2-morpholinoethyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 2.44-2.47 (4H, t, J=4.5 Hz, (OCH₂CH₂N)₂), 2.66-2.71 (2H, t, J=7.5 Hz, CH₂CH₂), 3.30-3.35 (2H, t, J=7.5 Hz, CH₂CH₂), 3.68-3.71 (4H, t, J=4.8 Hz, (OCH₂CH₂N)₂), 5.30 (1H, s, CH—C═N), 6.48-6.51 (1H, d, J=7.81 Hz, PhH₆), 6.89 (1H, s, CH═C—NH), 7.13-7.23 (2H, m, PhH_7,8), 7.29-7.35 (3H, m, PhH₉, Ph′H_2,6), 7.62-7.80 (5H, m, Ph′H_3,4,5, PyH₆, PyH₅), 8.34-8.35 (1H, d, J=3.91 Hz, PyH₄), 8.59 (1H, d, J=2.1 Hz, PyH₂). ¹³C NMR (100 MHz, CDCl₃) δ: 47.70, 54.02, 59.78, 66.91, 88.94, 99.54, 114.36, 123.09, 123.66, 127.92, 128.32, 128.62, 129.82, 131.43, 135.11, 135.69, 136.70, 137.48, 143.34, 143.90, 144.36, 150.68, 152.92. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₉N₆O: 477.2397: found: 477.2399.

TBI-057, 5-phenyl-3-N-isobutyl-4-piperidyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 0.88-0.90 (6H, d, J=6.6 Hz, CH(CH₃)₂), 1.60-1.91 (7H, m, (CH₂CH₂N)₂, CH(CH₃)₂, CH₂CH₂N), 2.03-2.05 (2H, d, J=7.5 Hz, CH₂CH), 2.75-2.79 (2H, m, CH₂CH₂N), 3.05-3.08 (1H, m, NCHCH₂CH₂N), 5.24 (1H, s, CH—C═N), 6.51-6.54 (1H, d, J=7.5 Hz, PhH₆), 6.86 (1H, s, CH═C—NH), 7.11-7.20 (2H, m, PhH_7,8), 7.29-7.35 (3H, m, PhH₉, Ph′_2,6), 7.63-7.80 (5H, m, Ph′H_3,4,5, PyH₆, PyH₅), 8.32-8.33 (1H, d, J=4.2 Hz, PyH₄), 8.58 (1H, d, J=2.4 Hz, PyH₂). ¹³C NMR (100 MHz, CDCl₃) δ: 20.96, 25.70, 32.78, 52.51, 56.0, 67.11, 89.22, 99.43, 114.18, 122.84, 123.63, 127.74, 128.24, 128.74, 129.70, 131.23, 131.67, 135.06, 135.67, 136.90, 137.55, 143.58, 143.88, 144.18, 151.06. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₂H₃₅N₆: 503.2923; found: 503.2962.

TBI-058, 5-Phenyl-3-(4-tetrahydropyranyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.60 (4H, m), 3.27-3.41 (3H, m), 3.94-3.97 (2H, m), 5.24 (1H, s, CH—C═N), 6.52-6.55 (1H, d, J=7.5 Hz, PhH₆), 6.88 (1H, s, CH═C—NH), 7.13-7.22 (2H, m, PhH₇, s), 7.28-7.35 (3H, on. PhH₉, Ph′H_2,6), 7.63-7.80 (5H, m, Ph′H_3,4,5, PyH₆, PyH₅), 8.33-8.35 (1H, d, J=4.2 Hz, PyH₄), 8.59 (1H, d, J=2.4 Hz, PyH₂). ¹³C NMR (100 MHz, CDCl₃) δ: 33.37. 54.43, 66.20, 88.96, 99.58, 114.24, 122.97, 123.64, 127.87, 127.94, 128.31, 128.6, 129.77, 131.25, 131.56, 135.16, 135.65, 136.72, 137.51, 143.55, 143.95, 144.35, 150.71, 151.28. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₆N₅O: 448.2137; found: 448.2100.

TBI-059, 5-Phenyl-3-(4-methoxycyclohexyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.07-1.18 (2H, q), 1.33-1.45 (2H, q), 1.66-1.69 (2H, d), 2.04-2.07 (2H, q), 2.99-3.06 (1H, m), 3.13-3.21 (1H, m), 3.35 (3H, s), 5.23 (1H, s, CH—C═N), 6.52-6.55 (1H, d, J=7.5 Hz, PhH₆), 6.85 (1H, s, CH═C—NH), 7.12-7.20 (2H, m, PhH_7,8), 7.28-7.33 (3H, m, PhH₉, Ph′H_2,6), 7.61-7.80 (5H, m, Ph′H_3,4,5, PyH₆, PyH₅), 8.32-8.33 (1H, d, J=4.2 Hz, PyH₄), 8.57 (1H, d, J=2.4 Hz, PyH₂). ¹³C NMR (100 MHz, CDCl₃) δ: 30.04, 31.15, 55.85, 57.45, 78.56, 89.17, 99.50, 114.20, 122.85, 123.61, 127.79, 128.25, 128.68, 129.82, 131.22, 131.65, 135.06, 135.64, 136.82, 137.46, 143.52, 143.90, 144.22, 150.88, 151.35. HRMS (ESI-TOF⁺): m/z[M+H]⁺ calcd for C₃₀H₃₀N₅O: 476.2450; found: 476.2427.

TBI-060, 5-Phenyl-3-(N-cyclopentyl-4-piperidyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.23-2.04 (14H, m), 2.45 (1H, brs), 2.91 (2H, brs), 3.12 (1H, brs), 5.24 (1H, s, CH—C═N), 6.51-6.54 (1H, d, J=7.8 Hz, PhH₆), 6.87 (1H, s, CH═C—NH), 7.15-7.19 (2H, m, PhH_7,8), 7.28-7.34 (1H, m, PhH₉, Ph′H_2-6), 7.64-7.79 (5H, m, Ph′H_3,4,5. PyH₆, PyH₅), 8.32-8.34 (1H, d, J=4.8 Hz, PyH₄), 8.57 (1H, s, PyH₂). ¹³C NMR (125 MHz, CDCl₃) 24.15, 30.66, 32.62, 50.95, 55.48, 67.70, 89.13, 99.51, 114.23, 122.91, 123.64, 127.79, 128.30, 128.70, 129.77, 131.26, 131.63, 135.12, 135.70, 136.86, 137.54, 143.53, 143.92, 144.25, 151.11. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₃H₃₅N₆: 515.2918: found: 515.2913.

TBI-061, 5-Phenyl-3-(1-methylethyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.07-1.09 (6H, d, J=6.0 Hz, CH(CH-3)₂), 3.36-3.45 (1H, m, J=6.0 Hz, CH(CH₃)₂), 4.03 (3H, s, CH₃), 5.27 (1H, s, CH—C═N), 6.45-6.48 (1H, d, J=7.5 Hz, PhH₆), 6.88-6.91 (1H, m, PhH₉), 6.93 (1H, s, CH═C—NH), 7.08-7.18 (2H, m, PhH_7,8), 7.32-7.35 (2H, m, Ph′H_2,6), 7.61-7.66 (1H, m, PyH₅), 7.68-7.75 (3H, m, Ph′H_3,4,5), 7.80-7.83 (1H, d, J=4.8 Hz, PyH₆), 7.84-7.87 (1H, d, J=7.8 Hz, PyH₄). ¹³C NMR (100 MHz, CDCl₃) δ: 23.50, 49.29, 53.69, 89.27, 100.10, 114.07, 116.78, 122.64, 124.84, 124.96, 127.53, 128.07, 128.85, 129.65, 131.23, 131.87, 134.96, 135.61, 137.65, 138.69, 142.91, 150.81, 151.29, 155.47. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₆N₅O: 436.2137; found: 436.2172.

TBI-062, 5-Phenyl-3-(N-methyl-4-piperidyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.66 (4H, brs, (CH₂CH₂N)₂), 2.10 (2H, m, CH₂CH₂N), 2.29 (3H, s, CH₃), 2.73-2.77 (2H, m, CH₂CH₂N), 3.16 (1H, m, NCHCH₂CH₂N), 4.03 (3H, s, CH₃), 5.23 (1H, s, CH—C═N), 6.48-6.51 (1H, d, J=7.5 Hz, PhH₆), 6.89-6.93 (1H, m, PhH₉), 6.97 (1H, s, CH═C—NH), 7.10-7.19 (2H, m, PhH_7,8), 7.31-7.34 (2H, m, Ph′H_2,6), 7.62-7.75 (4H, m, PyH₅, Ph′H_3,4,5), 7.78-7.80 (1H, d, J=4.8 Hz, PyH₆), 7.84-7.87 (1H, d, J=7.8 Hz, PyH₄), 9.08 (1H, s, NH). ¹³C NMR (100 MHz, CDCl₃) δ: 32.63, 46.51, 53.52, 53.67, 89.10, 100.19, 114.14, 116.82, 122.76, 124.10, 125.03, 127.65, 128.15, 128.77, 128.89, 129.69, 131.24, 131.76, 135.08, 135.64, 137.56, 138.46, 142.60, 151.18, 155.25. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₃₁N₆O: 491.2554; found: 491.2556.

TBI-063, 5-Phenyl-3-(4-methoxycyclohexyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.06-1.22 (2H, q), 1.35-1.47 (2H, q), 1.68-1.71 (2H, d), 2.04-2.07 (2H, d), 3.02-3.08 (1H, m), 3.18-3.24 (1H, m), 3.35 (3H, s), 4.02 (3H, s, CH₃), 5.22 (1H, s, CH—C═N), 6.51-6.53 (1H, d, J=7.5 Hz, PhH₆), 6.88-6.91 (1H, m, PhH₉), 6.94 (1H, s, CH═C—NH), 7.10-7.19 (2H, m, PhH_7,8), 7.31-7.33 (2H, m, Ph′H_2,6), 7.60-7.65 (1H, m, PyH₅), 7.68-7.71 (3H, m, Ph′H_3,4,5), 7.79-7.81 (1H, d, J=4.8 Hz, PyH₆), 7.84-7.86 (1H, d, J=7.8 Hz, PyH₄), 8.93 (1H, s, NH). ¹³C NMR (100 MHz, CDCl₃) δ: 29.66, 30.83, 53.68, 55.82, 57.08, 78.42, 89.32, 100.21, 114.13, 116.82, 122.72, 124.61, 124.94, 127.65, 128.15, 128.74, 129.75, 131.21, 131.77, 134.99, 135.64, 137.52, 138.64, 142.74, 151.19, 151.53, 155.35. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₂N₅O₂: 506.2556; found: 506.2585.

TBI-064, 5-Phenyl-3-(N-isobutyl-4-piperidyl)imino-2-(2-ethoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 0.89-0.91 (6H, d, J=6.6 Hz, CH(CH₃)₂), 1.62-1.82 (5H, m, (CH₂CH₂N)₂, CH(CH₃)₂), 1.96 (2H, m, CH₂CH₂N), 2.05-2.07 (2H, d, J=7.5 Hz, CH₂CH), 2.74-2.77 (2H, m, CH₂CH₂N), 3.10-3.12 (1H, m, NCHCH₂CH₂N), 4.03 (3H, s, CH₃), 5.24 (1H, s, CH—C═N), 6.48-6.51 (1H, d, J=7.2 Hz, PhH₆), 6.89-6.93 (1H, m, PhH₉), 6.96 (1H, s, CH═C—NH), 7.10-7.19 (2H, m, PhH_7,8), 7.31-7.34 (2H, d, J=7.2 Hz, Ph′H_2,6), 7.62-7.75 (4H, m, PyH₅, Ph′H_3,4,5), 7.79-7.80 (1H, d, J=4.8 Hz, PyH₆), 7.84-7.87 (1H, d, J=8.1 Hz, PyH₄), 9.06 (1H, s, NH). ¹³C NMR (100 MHz, CDCl₃) δ: 21.04, 25.68, 32.75, 52.18, 53.68, 55.32, 67.38, 89.28, 100.17, 114.10, 116.80, 122.70, 124.26, 125.03, 127.59, 128.13, 128.80, 129.64, 131.21, 131.80, 135.01, 135.64, 137.60, 138.49, 142.70, 151.12, 151.28, 155.31. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₃H₃₇N₆O: 533.3023; found: 533.3019.

TBI-065, 5-Phenyl-3-(2-morpholinoethyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 2.49-2.52 (4H, t, J=4.5 Hz, (OCH₂CH₂N)₂), 2.70-2.75 (2H, t, J=6.9 Hz, CH₂CH₂), 3.30-3.34 (2H, t, J=7.2 Hz, CH₂CH₂), 3.68-3.71 (4H, t, J=4.81 Hz, (OCH₂CH₂N)₂), 4.03 (3H, s, CH₃), 5.27 (1H, s, CH—C═N), 6.47-6.49 (1H, d, J=7.5 Hz, PhH₆), 6.89-6.94 (1H, m, PhH₉), 6.98 (1H, s, CH═C—NH), 7.11-7.22 (2H, m, PhH_7,8), 7.31-7.34 (2H, d, J=7.2 Hz, Ph′H_2,6), 7.61-7.74 (4H, m, PyH₅, Ph′H_3,4,5), 7.80-7.82 (1H, d, J=4.5 Hz, PyH₆), 7.85-7.88 (1H, d, J=7.5 Hz, PyH₄), 8.85 (1H, s, NH). ¹³C NMR (100 MHz, CDCl₃) δ: 48.31, 53.72, 54.18, 59.80, 67.00, 89.10, 100.17, 114.30, 116.85, 122.96, 124.64, 124.81, 127.79, 128.21, 128.68, 129.75, 131.41, 131.72, 135.03, 135.69, 137.54, 138.76, 142.51, 151.01, 153.05, 155.31. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₃₁N₆O): 507.2503: found: 507.2505.

TBI-066, 5-Phenyl-3-(4-tetrahydropyranyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.60-1.66 (4H, m), 3.34-3.48 (3H, m), 3.96-4.05 (5H, m), 5.23 (1H, s, CH—C═N), 6.49-6.53 (1H, d, J=7.5 Hz, PhH₆), 6.90-6.94 (1H, m, PhH₉), 6.98 (1H, s, CH═C—NH), 7.11-7.21 (2H, m, PhH_7,8), 7.32-7.35 (2H, m, Ph′H_2,6), 7.62-7.75 (4H, m, PyH₅, Ph′H_3,4,5), 7.80-7.82 (1H, d, J=4.8 Hz, PyH₆), 7.84-7.87 (1H, d, J=7.8 Hz, PyH₄). ¹³C NMR (100 MHz, CDCl₃) δ: 33.29, 53.47, 53.674, 89.02, 100.30, 114.19, 116.83, 122.87, 124.32, 124.93, 127.74, 128.21, 128.75, 129.73, 131.25, 131.68, 135.15, 135.65, 137.55, 138.63, 142.63, 151.02, 151.37, 155.30. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₈N₅O: 478.2243; found: 478.2272.

TBI-067, 5-Phenyl-3-(1-methylethyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.06-1.08 (6H, d, J=6.0 Hz, CH(CH₃)₂), 2.55 (1H, s, CH₃), 3.37-3.45 (1H, m, J=6.0 Hz, CH(CH₃)₂), 5.27 (1H, s, CH—C═N), 6.46-6.49 (1H, d, J=7.8 Hz, PhH₆), 6.73 (1H, s, CH═C—NH), 7.08-7.18 (3H, m, PhH_7,8,9), 7.32-7.34 (2H, d, J=7.2 Hz, PhH_2-6) 7.61-7.74 (5H, m, Ph′H_3,4,5, PyH_4,5), 8.44-8.45 (1H, d, J=2.4 Hz, PyH₂). ¹³C NMR (100 MHz, CDCl₃) δ: 23.49, 23.81, 49.28, 89.07, 98.80, 114.10, 122.70, 123.12, 127.43, 128.07, 128.80, 129.33, 129.67, 131.21, 131.67, 134.16, 135.00, 135.62, 137.64, 143.71, 144.38, 150.61, 151.00, 153.20. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₂H₂₆N₅: 420.2183: found: 420.2181.

TBI-068, 5-Phenyl-3-(N-isobutyl-4-piperidyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 0.87-0.89 (6H, d, J=6.6 Hz, CH(CH₃)₂), 1.59-1.89 (7H, m, (CH₂CH₂N)₂, CH(CH₃)₂, CH₂CH₂N), 2.02-2.04 (2H, d, J=6.91 Hz, CH₂CH), 2.55 (3H, s, CH₃), 2.74-2.78 (2H, m, CH₂CH₂N), 3.04-3.07 (1H, m, NCHCH₂CH₂N), 5.23 (1H, s, CH—C═N), 6.50-6.53 (1H, d, J=7.8 Hz, PhH₆), 6.74 (1H, s, CH═C—NH), 7.09-7.19 (3H, m, PhH_7,8,9), 7.31-7.33 (2H, d, J=6.9 Hz, Ph′H_2,6), 7.62-7.75 (5H, m, Ph′H_3,4,5, PyH_4,5), 8.43-8.44 (1H, d, J=2.4 Hz, PyH₂). ¹³C NMR (100 MHz, CDCl₃) δ: 20.96, 23.83, 25.71, 32.79, 52.54, 56.07, 67.10, 89.21, 98.82, 114.14, 122.76, 123.14, 127.50, 128.14, 128.76, 129.26, 129.65, 131.20, 131.60, 134.14, 135.00, 135.67, 137.61, 143.69, 144.32, 151.11, 153.23. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₃H₃₇N₆: 517.3074: found: 517.3076.

TBI-069, 5-Phenyl-3-(N-methyl-4-piperidyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.65 (4H, brs, (CH₂CH₂N)₂), 2.04 (2H, m, CH₂CH₂N), 2.27 (3H, s, CH₃), 2.56 (3H, s, CH₃), 2.75-2.79 (2H, m, CH₂CH₂N), 3.07 (1H, m, NCHCH₂CH₂N), 5.23 (1H, s, CH—C═N), 6.51-6.53 (1H, d, J=7.5 Hz, PhH₆), 6.74 (1H, s, CH═C—NH), 7.15-7.17 (3H, m, PhH_7,8,9), 7.31-7.34 (2H, d, J=7.5 Hz, Ph′H_2,6), 7.66-7.75 (5H, m, Ph′H_3,4,5, PyH_4,5), 8.45-8.46 (1H, d, J=2.1 Hz, PyH₂). ¹³C NMR (100 MHz, CDCl₃) δ: 23.83, 32.38, 32.61, 46.37, 54.08, 54.48, 89.12, 98.89, 114.21, 122.87, 123.17, 127.60, 128.20, 128.71, 129.49, 129.72, 131.22, 131.52, 134.06, 135.04, 135.71, 137.58, 143.81, 144.31, 151.32, 153.38. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₃₁N₆: 475.2610; found: 475.2597.

TBI-070, 5-Phenyl-3-(4-tetrahydropyranyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.61-1.67 (4H, m), 2.56 (3H, s, CH₃), 3.30-3.47 (3H, m), 3.93-3.97 (2H, m), 5.23 (1H, s, CH—C═N), 6.51-6.54 (1H, d, J=7.5 Hz, PhH₆), 6.75 (1H, s, CH═C—NH), 7.11-7.21 (3H, m, PhH_7,8,9), 7.32-7.34 (2H, d, J=7.5 Hz, Ph′H_2,6), 7.63-7.75 (5H, m, Ph′H_3,4,5, PyH_4,5), 8.46 (1H, s). ¹³C NMR (100 MHz, CDCl₃) δ: 23.82, 33.39, 54, 46, 66.23, 88.95, 98.97, 114.22, 122.92, 123.19, 127.66, 128.22, 128.72, 129.51, 129.74, 131.24, 131.49, 134.00, 135.12, 135.67, 137.58, 143.79, 144.34, 150.76, 151.36, 153.46. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₈N₅O: 462.2293; found: 462.2316.

TBI-072, 5-Phenyl-3-(4-methoxycyclohexyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.06-1.18 (2H, q), 1.34-1.45 (2H, q), 1.65-1.69 (2H, d), 2.04-2.07 (2H, d), 2.55 (3H, s, CH₃), 2.98-3.05 (1H, m), 3.13-3.20 (1H, m), 3.35 (3H, s), 5.22 (1H, s, CH—C═N), 6.51-6.54 (1H, d, J=8.1 Hz, PhH₆), 6.73 (1H, s, CH═C—NH), 7.10-7.19 (3H, m, PhH_7,8,9), 7.30-7.33 (2H, d, J=6.9 Hz, Ph′H_2,6), 7.60-7.73 (5H, m, Ph′H_3,4,5, PyH_4,5), 8.43-8.44 (1H, d, J=2.4 Hz, PyH₂). ¹³C NMR (125 MHz, CDCl₃) δ: 23.81, 30.07, 31.18, 55.84, 57.50, 78.60, 89.16, 98.91, 114.17, 122.77, 123.14, 127.58, 128.17, 128.71, 129.33, 129.78, 131.20, 131.59, 134.09, 135.01, 135.68, 137.54, 143.74, 144.32, 150.92, 151.43, 153.30. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₂N₅O: 490.2606; found: 490.2586.

TBI-073, 5-Phenyl-3-(1-methylethyl)imino-2-(2-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.07-1.09 (6H, d, J=6.0 Hz, CH(CH₃)₂), 2.55 (1H, s, CH₃), 3.39-3.47 (1H, m, J=6.0 Hz, CH(CH₃)₂), 5.28 (1H, s, CH—C═N), 6.47-6.50 (1H, d, J=7.8 Hz, PhH₆), 6.60 (1H, s, CH═C—NH), 7.09-7.20 (3H, m, PhH_7,8,9), 7.33-7.36 (2H, d, J=7.8 Hz, Ph′H_2,6), 7.62-7.76 (4H, m, Ph′H_3,4,5, PyH₅), 7.81-7.84 (1H, d, J=8.1 Hz, PyH₄), 8.44-8.45 (1H, d, J=4.5 Hz, PyH₆). ¹³C NMR (100 MHz, CDCl₃) δ: 2092, 23.52, 49.18, 89.03, 98.82, 114.14, 121.63, 122.74, 127.47, 128.07, 128.80, 128.95, 129.71, 131.24, 131.69, 134.87, 135.07, 135.61, 137.65, 144.02, 144.12, 150.53, 151.01, 152.12. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₆N₅: 420.2188; found: 420.2167.

TBI-075, 5-Phenyl-3-(4-tetrahydropyranyl)imino-2-(2-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.60-1.66 (4H, m), 2.56 (3H, s, CH₃), 3.33-3.46 (3H, m), 3.93-3.99 (2H, m), 5.25 (1H, s, CH—C═N), 6.51-6.55 (1H, d J=7.5 Hz, PhH₆), 6.65 (1H, s, CH═C—NH), 7.12-7.21 (3H, m, PhH_7,8,9), 7.33-7.35 (2H, d, J=6.9 Hz, Ph′H_2,6), 7.64-7.76 (4H, m, Ph′H_3,4,5, PyH₅), 7.83-7.86 (1H, d, J=8.1 Hz, PyH₄), 8.27-8.29 (1H, d, J=4.8 Hz, PyH₆). ¹³C NMR (100 MHz, CDCl₃) δ: 20.95, 33.19, 53.82, 65.96, 88.90, 99.01, 114.24, 121.67, 122.95, 127.71, 128.21, 128.71, 128.90, 129.77, 131.26, 131.52, 134.68, 135.19, 135.64, 137.56, 143.94, 144.13, 150.75, 151.27, 152.04. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₈N₅O: 462.2293; found: 462.2278.

TBI-076, 5-Phenyl-3-(4-methoxycyclohexyl)imino-2-(2-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.09-1.22 (2H, q), 1.32-1.45 (2H, q), 1.68-1.71 (2H, d), 2.03-2.06 (2H, d), 2.53 (3H, s, CH₃), 3.02-3.09 (1H, m), 3.16-3.22 (1H, m), 3.35 (3H, s, CH₃), 5.24 (1H, s, CH—C═N), 6.52-6.55 (1H, d, J=7.8 Hz, PhH₆), 6.61 (1H, s, CH═C—NH), 7.11-7.20 (3H, m, PhH_7,8,9), 7.31-7.34 (2H, d, J=7.2 Hz, Ph′H_2,6), 7.61-7.74 (4H, m, Ph′H_3,4,5, PyH₅), 7.81-7.84 (1H, d, J=8.1 Hz, PyH₄), 8.26-8.27 (1H, d, J=4.5 Hz, PyH₆). ¹³C NMR (100 MHz, CDCl₃) δ: 20.91, 29.82, 31.03, 55.83, 57.13, 89.12, 98.92, 114.19, 121.65, 122.80, 127.62, 128.14, 128.69, 128.88, 129.79, 131.21, 131.59, 134.76, 135.06, 135.62, 137.52, 143.96, 144.04, 150.91, 151.33, 152.01. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₂N₅O: 490.2606; found: 490.2591.

TBI-077, 5-Phenyl-3-cyclohexylimino-2-(2-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.15-1.42 (5H, m), 1.58-1.63 (3H, m), 1.70-1.73 (2H, m), 2.54 (3H, s, CH₃), 3.05-3.11 (1H, m), 5.26 (1H, s, CH—C═N), 6.50-6.53 (1H, d, J=7.5 Hz, PhH₆), 6.62 (1H, s, CH═C—NH), 7.09-7.20 (3H, m, PhH_7,8,9), 7.32-7.35 (2H, d, J=7.2 Hz, Ph′H_2,6), 7.62-7.75 (4H, m, Ph′H_3,4,5, PyH₅), 7.81-7.84 (1H, d, J=7.8 Hz, PyH₄), 8.25-8.27 (1H, d, J=4.5 Hz, PyH₆). ¹³C NMR (100 MHz, CDCl₃) δ: 20.94, 24,46, 25.88, 33.57, 57.44, 89.28, 98.80, 114.12, 121.63, 122.72, 127.46, 128.07, 128.68, 128.78, 129.61, 131.19, 131.66, 134.94, 135.01, 135.64, 137.65, 143.88, 144.06, 150.64, 151.07, 151.94. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₃₀N₅: 460.2501; found: 460.2486.

TBI-078, 5-Phenyl-3-methylimino-2-(2-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 2.55 (3H, s, CH₃), 3.06 (3H, s, CH₃), 5.33 (1H, s, CH—C═N), 6.51-6.53 (2H, m, CH═C—NH, PhH₆), 7.13-7.23 (3H, m, PhH_7,8,9), 7.33-7.36 (2H, d, J=7.5 Hz, Ph′H_2,6), 7.63-7.79 (5H, m, Ph′H_3,4,5, PyH₅, PyH₄), 8.31-8.32 (1H, d, J=3.6 Hz, PyH₆). ¹³C NMR (100 MHz, CDCl₃) δ: 21.01, 37.21, 88.52, 99.01, 114.40, 121.72, 123.12, 127.79, 128.23, 128.56, 129.85, 130.23, 131.37, 134.49, 135.02, 135.79, 137.52, 144.24, 144.76, 152.95, 154.23. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₅H₂₂N₅: 392.1875: found: 392.1861.

TBI-079, 5-Phenyl-3-cyclohexylimino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.16-1.76 (10H, m), 3.05-3.08 (1H, m), 4.03 (3H, s, CH₃), 5.25 (1H, s, CH—C═N), 6.49-6.52 (1H, d, J=8.1 Hz, PhH₆), 6.89-6.94 (2H, m, PhH₉, CH═C—NH), 7.09-7.19 (2H, m, PhH_7,8), 7.32-7.35 (2H, d, J=7.51 Hz, Ph′H_2,6), 7.61-7.75 (4H, m, PyH₅, Ph′H_3,4,5), 7.79-7.81 (1H, d, J=4.8 Hz, PyH₆), 7.84-7.87 (1H, d, J=7.8 Hz, PyH₄). ¹³C NMR (100 MHz, CDCl₃) δ: 24.33, 25.97, 33.49, 53.68, 57.41, 89.49, 100.12, 114.04, 116.80, 122.61, 124.47, 125.05, 127.52, 128.07, 128.84, 129.55, 131.18, 131.86, 134.91, 135.62, 137.64, 138.53, 142.84, 150.81, 151.38, 155.37. HRMS (ESI-TOF⁺): [M+H]⁺ calcd for C₃₀H₃₀N₅O: 476.2450; found: 476.2432.

TBI-080, 5-Phenyl-3-cyclohexylimino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.07-1.41 (5H, m), 1.58-2.04 (5H, m), 2.55 (3H, s, CH₃), 2.99-3.06 (1H, m), 5.24 (1H, s, CH—C═N), 6.50-6.52 (1H, d, J=7.5 Hz, PhH₆), 6.73 (1H, s, CH═C—NH), 7.09-7.18 (3H, m, PhH_7,8,9), 7.32-7.34 (2H, d, J=7.2 Hz, PhH_2,6), 7.61-7.75 (5H, m, Ph′H_3,4,5, PyH_4,5), 8.43-8.44 (1H, d, J=2.4 Hz, PyH₂). ¹³C NMR (100 MHz, CDCl₃) δ: 23.80, 24.71, 25.82, 33.60, 57.97, 89.36, 98.78, 114.08, 122.68, 123.13, 127.42, 128.08, 128.79, 129.28, 129.57, 131.17, 131.64, 134.20, 134.93, 135.65, 137.65, 143.67, 144.40, 150.76, 151.07, 153.15. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₃₀N₅: 460.2501; found: 460.2485.

TBI-081, 5-Phenyl-3-(1-methylethyl)imino-2-(5-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.05-1.08 (6H, d, J=6.3 Hz, CH(CH₃)₂), 2.04 (3H, s, CH₃), 3.37-3.45 (1H, m, J=6.0 Hz, CH(CH₃)₂), 5.27 (1H, s, CH—C═N), 6.47-6.50 (1H, d, J=7.8 Hz, PhH₆), 6.84 (1H, s, CH═C—NH), 7.09-7.19 (2H, m, PhH_7,8), 7.32-7.35 (2H, d, J=7.2 Hz, Ph′H_2,6), 7.59-7.75 (5H, m, Ph′H_3,4,5, PyH₄, PhH₉), 8.16 (1H, s, PyH₆), 8.39-8.40 (1H, d, J=2.1 Hz, PyH₂). ¹³C NMR (100 MHz, CDCl₃) δ: 18.47, 23.49, 49.28, 89.10, 99.32, 114.15, 122.75, 127.58, 128.10, 128.28, 128.80, 129.71, 131.25, 131.74, 133.46, 135.05, 135.61, 136.53, 137.61, 141.08, 143.75, 144.83, 150.55, 151.06. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₆N₅: 420.2188; found: 420.2178.

TBI-082, 5-Phenyl-3-cyclohexylimino-2-(5-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.07-1.41 (5H, m), 1.56-1.74 (5H, m), 2.37 (3H, s. CH₃), 2.99-3.06 (1H, m), 5.24 (1H, s, CH—C═N), 6.50-6.53 (1H, d, J=7.5 Hz, PhH₆), 6.83 (1H, s, CH═C—NH), 7.10-7.19 (2H, m, PhH_7,8), 7.32-7.34 (2H, d, 6.9 Hz, Ph′H_2,6), 7.58-7.75 (5H, m, Ph′H_3,4,5, PyH₄, PhH₉), 8.16 (1H, S, PyH₆), 8.38-8.39 (1H, d, J=1.8 Hz, PyH₂). ¹³C NMR (100 MHz, CDCl₃) δ: 18.46, 24.67, 25.82, 33.58, 57.90, 89.38, 99.28, 114.11, 122.72, 127.56, 128.09, 128.21, 128.78, 129.60, 131.19, 131.69, 133.45, 134.96, 135.63, 136.58, 137.61, 141.03, 143.76, 144.75, 150.69, 151.11. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₃₀N₅: 460.2501; found: 460.2498.

TBI-083, 5-Phenyl-3-(4-tetrahydropyranyl)imino-2-(5-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR 300 MHz, CDCl₃) δ: 1.60-1.66 (4H, m), 2.38 (3H, s, CH₃), 3.28-3.39 (3H, m), 3.93-3.97 (2H, m), 5.24 (1H, s, CH—C═N), 6.52-6.54 (1H, d, J=7.8 Hz, PhH₆), 6.87 (1H, s, CH═C—NH), 7.12-7.22 (2H, m, PhH_7,8), 7.32-7.34 (2H, 7.5 Hz, Ph′H_2,6), 7.58-7.76 (5H, m, Ph′H_3,4,5, PyH₄, PhH₉), 8.18 (1H, s, PyH₆), 8.38-8.39 (1H, s, PyH₂). ¹³C NMR (100 MHz, CDCl₃) δ: 18.46, 33.36, 54.39, 66.19, 88.98, 99.48, 114.24, 122.96, 127.80, 128.23, 128.43, 128.71, 129.76, 131.25, 131.54, 133.53, 135.15, 135.63, 136.34, 137.53, 141.08, 143.65, 144.99, 150.79, 151.29. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₈N₅O: 462.2293; found: 462.2297.

TBI-084, 5-Phenyl-3-(4-methoxycyclohexyl)imino-2-(5-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.07-1.18 (2H, q), 1.34-1.45 (2H, q), 1.66-1.69 (2H, d), 2.05-2.07 (2H, d), 2.38 (3H, s, CH₃), 2.99-3.06 (1H, m), 3.14-3.21 (1H, m), 3.36 (3H, s, CH₃), 5.23 (1H, s, CH—C═N), 6.53-6.56 (1H, d, J=7.8 Hz, PhH₆), 6.85 (1H, s, CH═C—NH), 7.12-7.21 (2H, m, PhH₇, s), 7.32-7.34 (2H, d, J=6.9 Hz, Ph′H_2,6), 7.59-7.74 (5H, m, PyH₄, PhH₉), 8.17 (1H, s, PyH₆), 8.38-8.39 (1H, s, J=1.81 Hz, PyH₂). ¹³C NMR (100 MHz, CDCl₃) δ: 18.45, 30.03, 31.11, 55.85, 57.41, 78.54, 89.21, 99.41, 114.21, 122.85, 127.75, 128.18, 128.66, 129.83, 131.23, 131.61, 133.51, 135.03, 135.64, 136.41, 137.45, 141.06, 143.60, 144.87, 150.91, 151.37. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₂N₅O: 490.2606; found: 490.2613.

TBI-085, 5-Phenyl-3-(4-hydroxycyclohexyl)imino-2-(5-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.15-1.26 (2H, q), 1.38-1.49 (2H, q), 1.64-1.68 (2H, d), 1.95-1.99 (2H, q), 2.38 (3H, s, CH₃), 2.98-3.05 (1H, m), 3.65-3.72 (1H, m), 5.23 (1H, s, CH—C═N), 6.52-6.56 (1H, d, J=7.8 Hz, PhH₆), 6.85 (1H, s, CH═C—NH), 7.12-7.21 (2H, m, PhH_7,8), 7.32-7.35 (2H, d, J=7.2 Hz, Ph′H_2,6), 7.59-7.75 (5H, m, Ph′H_3,4,5, PyH₄, PhH₉), 8.16 (1H, s, PyH₆), 8.38-8.39 (1H, d, J=2.1 Hz, PyH₂). ¹³C NMR (100 MHz, CDCl₃) δ: 18.46, 31.21, 33.73, 57.20, 70.01, 89.15, 99.40, 114.20, 122.85, 127.74, 128.17, 128.29, 128.71, 129.78, 131.23, 131.62, 133.51, 135.04, 135.62, 136.41, 137.51, 141.03, 143.62, 144.85, 150.93, 151.39. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for [M+H]⁺ calcd for C₃₉H₃₀N₅O: 476.2450; found: 476.2467.

TBI-086, 5-Phenyl-3-(4-hydroxycyclohexyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.14-1.28 (2H, q), 1.38-1.49 (2H, q), 1.64-1.68 (2H, d), 1.95-1.98 (2H, q), 2.55 (3H, s, CH₃), 2.98-3.05 (1H, m), 3.64-3.71 (1H, m), 5.22 (1H, s, CH—C═N), 6.51-6.54 (1H, d, 7.8 Hz, PhH₆), 6.73 (1H, s, CH═C—NH), 7.11-7.19 (3H, m, PhH_7,8,9), 7.31-7.34 (2H, d, J=7.2 Hz, Ph′H_2,6), 7.62-7.75 (5H, m, Ph′H_3,4,5, PyH_4,5), 8.43 (1H, d, J=2.1 Hz, PyH₂). ¹³C NMR (100 MHz, CDCl₃) δ: 23.78, 31.23, 33.76, 57.24, 70.01, 89.12, 98.87, 114.17, 122.80, 123,18, 127.60, 128.14, 128.71, 129.35, 129.75, 131.21, 131.56, 134.08, 135.01, 135.63, 137.54, 143.63, 144.26, 150.87, 151.45, 153.26. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₃₀N₅O: 476.2450; found: 476.2458.

TBI-087, 5-Phenyl-3-(4-hydroxycyclohexyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.17-1.28 (2H, q), 1.40-1.52 (2H, q), 1.67-1.70 (2H, d), 1.97-1.99 (2H, q), 3.00-3.07 (1H, m), 3.67-3.75 (1H, m), 4.02 (3H, s, CH₃), 5.22 (1H, s, CH—C═N), 6.51-6.53 (1H, d, J=8.7 Hz, PhH₆), 6.89-6.95 (2H, m, PhH₉, CH═C—NH), 7.10-7.19 (2H, m, PhH_7,8), 7.32-7.34 (2H, d, J=7.2 Hz, Ph′H_2,6), 7.62-7.74 (4H, m, PyH₅, Ph′H_3,4,5), 7.79-7.81 (1H, J=3.9 Hz, PyH₆), 7.84-7.86 (1H, d, J=7.8 Hz, PyH₄). ¹³C NMR (100 MHz, CDCl₃) δ: 30.91, 33.43, 53.70, 56.91, 69.92, 89.28, 100.18, 114.13, 116.82, 122.75, 124.67, 124.90, 127.67, 128.14, 128.76, 129.73, 131.22, 131.75, 134.99, 135.62, 137.54, 138.68, 142.74, 151.16, 151.60, 155.36. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₃₀N₅O₂: 492.2399; found: 492.2386.

TBI-088, 5-(4-Bromophenyl)-3-(1-methylethyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.10-1.12 (6H, d, J=6.3 Hz, CH(CH₃)₂), 3.44-3.52 (1H, m, J=6.0 Hz, CH(CH₃)₂), 5.30 (1H, s, CH—C═N), 6.44-6.46 (1H, d, J=7.5 Hz, PhH₆), 6.83 (1H, s, CH═C—NH), 7.11-7.18 (2H, m, PhH_7,8), 7.23-7.27 (2H, d, J=9.0 Hz, Ph′H_2,6), 7.30-7.32 (1H, m, PyH₅), 7.67-7.70 (1H, d, J=7.5 Hz, PyH₄), 7.77-7.80 (1H, d, J=8.1 Hz, PhH₉), 7.86-7.89 (2H, d, J=8.1 Hz, Ph′H_3,5), 8.33-8.34 (1H, d, J=4.5 Hz, PyH₆), 8.59 (1H, s, PyH₂). ¹³C NMR (100 MHz, CDCl₃) δ: 23.56, 49.40, 89.07, 99.43, 113.87, 123.00, 123.62, 123.79, 127.73, 127.93, 128.31, 130.71, 131.44, 134.70, 135.58, 136.57, 136.81, 143.68, 143.96, 144.28, 150.31, 150.95. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₆H₂₃BrN₅: 484.1136; found: 484.1126.

TBI-089, 5-(4-Bromophenyl)-3-cyclohexylimino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.09-1.41 (5H, m), 1.60-1.76 (5H, m), 3.10 (1H, brs), 5.26 (1H, s, CH—C═N), 6.47-6.49 (1H, d, J=7.2 Hz, PhH₆), 6.82 (1H, s, CH═C—NH), 7.11-7.31 (5H, m, PhH_7,8, Ph′H_2,6, PyH₅), 7.67-7.69 (1H, d, J=9.0 Hz, PyH₄), 7.76-7.79 (1H, d, J=8.7 Hz, PhH₉), 7.86-7.88 (2H, d, J=8.1 Hz, Ph′H_3,5), 8.32-8.33 (1H, d, J=4.2 Hz, PyH₆), 8.57 (1H, d, J=2.1 Hz, PyH₂). ¹³C NMR (100 MHz, CDCl₃) δ: 24.57, 25.82, 33.62, 57.84, 89.35, 99.40, 113.84, 122.98, 123.62, 127.72, 127.85, 128.31, 130.70, 131.39, 134.60, 134.72, 135.61, 136.56, 136.84, 143.68, 143.92, 144.22, 150.43, 150.99. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₇BrN₅: 524.1449; found: 524.1448.

TBI-090, 5-(4-Bromophenyl)-3-cyclopropylimino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 0.83 (2H, brs), 0.91-0.93 (2H, m), 2.76 (1H, brs), 5.56 (1H, s, CH—C═N), 6.42-6.44 (1H, d, J=7.8 Hz, PhH₆), 6.78 (1H, s, CH═C—NH), 7.10-7.17 (2H, m, PhH₇, s), 7.25-7.31 (3H, m, Ph′H_2,6, PyH₅), 7.66-7.68 (1H, d, J=7.2 Hz, PyH₄), 7.75-7.77 (1H, d, J=7.5 Hz, PhH₉), 7.86-7.88 (2H, J=8.4 Hz, Ph′H_3,5), 8.33-8.34 (1H, d, J=4.2 Hz, PyH₆), 8.57 (1H, s, PyH₂). ¹³C NMR (100 MHz, CDCl₃) δ: 10.04, 32.94, 89.47, 99.41, 113.82, 122.97, 123.64, 123.75, 127.75, 128.12, 128.26, 130.81, 131.60, 134.60, 134.75, 135.68, 136.56, 136.62, 143.43, 144.03, 144.39, 151.18, 152.25. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₆H₂₁BrN₅: 482.0980; found: 482.0970.

TBI-091, 5-(4-Bromophenyl)-3-(4-methoxycyclohexyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.16-1.26 (2H, q), 1.37-1.49 (2H, q), 1.69-1.72 (2H, d), 2.06-2.09 (2H, d), 3.08-3.24 (2H, m), 3.37 (3H, s, CH₃), 5.27 (1H, s, CH—C═N), 6.47-6.49 (1H, d, J=7.8 Hz, PhH₆), 6.84 (1H, s, CH═C—NH), 7.12-7.32 (5H, m, PhH_7,8, Ph′H_2,6, PyH₅), 7.68-7.71 (1H, d, J=9.0 Hz, PyH₄), 7.76-7.79 (1H, d, J=8.4 Hz, PhH₉), 7.85-7.88 (2H, d, J=8.4 Hz, Ph′H_3,5), 8.33-8.34 (1H, d, J=3.9 Hz, PyH₆), 8.57 (1H, d, J=2.4 Hz, PyH₂). ¹³C NMR (100 MHz, CDCl₃) δ: 29.83, 31.11, 55.83, 57.21, 78.45, 89.09, 99.53, 113.94, 123.08, 123.64, 123.86, 127.88, 128.37, 130.59, 131.37, 134.64, 134.79, 135.60, 136.41, 136.72, 143.54, 143.92, 144.31, 150.83, 151.03. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₂₉BrN₅O: 554.1555; found: 554.1536.

TBI-092, 5-Phenyl-3-(4-hydroxycyclohexyl)imino-2-(2-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.17-1.28 (2H, q), 1.37-1.49 (2H, q), 1.67-1.70 (2H, d), 1.95-1.99 (2H, q), 2.53 (3H, s), 3.01-3.08 (1H, m), 3.66-3.74 (1H, m), 5.24 (1H, s, CH—C═N), 6.52-6.55 (2H, d, J=7.8 Hz, PhH₆), 6.61 (1H, s, CH═C—NH), 7.11-7.20 (3H, PhH_7,8,9), 7.32-7.35 (2H, d, J=7.2 Hz, Ph′H_2,6), 7.63-7.75 (5H, m, Ph′H_3,4,5, PyH₅), 7.81-7.83 (1H, d, J=7.5 Hz, PyH₄), 8.26-8.27 (1H, d, J=3.9 Hz, PyH₆). ¹³C NMR (100 MHz, CDCl₃) δ: 20.87, 31.12, 33.56, 56.94, 69.86, 89.08, 98.91, 114.19, 121.67, 122.83, 127.64, 128.13, 128.69, 128.96, 129.78, 131.23, 131.57, 134.76, 135.06, 135.59, 137.53, 144.02, 150.87, 151.38, 152.04. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₃₀N₅O: 476.2450; found: 476.2455.

TBI-093, 5-(4-Bromophenyl)-3-(4-tetrahydropyranyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.63-1.69 (4H, m), 3.37-3.49 (3H, m), 3.97-4.01 (2H, m), 5.25 (1H, s, CH—C═N), 6.48-6.51 (1H, d, J=7.8 Hz, PhH₆), 6.86 (1H, s, CH═C—NH), 7.16-7.33 (5H, m, PhH_7,8, Ph′H_2,6, PyH₅), 7.70-7.73 (1H, d, J=7.5 Hz, PyH₄), 7.77-7.79 (1H, d, J=8.4 Hz, PhH₉), 7.87-7.89 (2H, d, J=8.1 Hz, Ph′H_3,5), 8.34-8.36 (1H, d, J=4.2 Hz, PyH₆), 8.60 (1H, d, J=1.8 Hz, PyH₂). ¹³C NMR (100 MHz, CDCl₃) δ: 33.37, 54.27, 66.06, 88.92, 99.60, 113.96, 123.20, 123.67, 123.85, 127.96, 128.04, 128.44, 130.61, 131.24, 134.68, 134.92, 135.61, 136.46, 136.63, 143.56, 143.96, 144.44, 150.66, 151.04. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₅BrN₅O: 526,1242; found: 526.1236.

TBI-094, 5-(4-Bromophenyl)-3-(4-hydroxycyclohexyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.22-1.33 (2H, q), 1.41-1.52 (2H, q), 1.67-1.70 (2H, d), 1.98-2.02 (2H, d), 3.06-3.13 (1H, m), 3.67-3.73 (1H, m), 5.25 (1H, s, CH—C═N), 6.47-6.49 (1H, d, J=7.5 Hz, PhH₆), 6.83 (1H, s, CH═C═N), 7.12-7.32 (5H, m, PhH_7,8. Ph′H_2,6, PyH₅), 7.68-7.71 (1H, d, J=7.2 Hz, PyH₄), 7.76-7.79 (1H, d, J=8.1 Hz, PhH₉), 7.86-7.88 (2H, d, J=8.41 Hz, Ph′H_3,5), 8.32-8.33 (1H, d, J=3.9 Hz, PyH₆), 8.56 (1H, d, J=2.4 Hz, PyH₂). ¹³C NMR (100 MHz, CDCl₃) δ: 31.23, 33.63, 57.06, 69.97, 89.07, 99.52, 113.93, 123.10, 123.66, 123.83, 127.91, 128.37, 130.62, 131.35, 134.65, 134.81, 135.59, 136.45, 136.71, 143.54, 143.88, 144.29, 150.80, 151.09. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₇BrN₅O: 540.1398; found: 540.1378.

TBI-095, 5-Phenyl-3-cyclopropylimino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 0.78-0.87 (4H, m), 2.55 (3H, s, CH₃), 2.68 (1H, hrs), 5.55 (1H, s, CH—C═N), 6.44-6.47 (1H, d, J=7.8 Hz, PhH₆), 6.68 (1H, s, CH═C—NH), 7.08-7.16 (3H, m, PhH_7,8,9), 7.34-7.37 (2H, d, J=7.5 Hz, Ph′H_2,6), 7.60-7.75 (5H, m, Ph′H_3,4,5, Py′H_3,4,5, PyH_4,5), 8.41 (1H, s, PyH₂). ¹³C NMR (100 MHz, CDCl₃) δ: 9.73, 23.80, 32.72, 89.47, 98.85, 114.11, 122.73, 123.18, 127.51, 128.05, 128.87, 129.65, 131.28, 131.83, 133.97, 134.85, 135.74, 137.63, 143.80, 144.14, 151.21, 152.78, 153.37. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₄N₅: 418.2031; found: 418.2022.

TBI-096, 5-Phenyl-3-cyclopropylimino-2-(5-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 0.77-0.84 (4H, m), 2.36 (3H, s, CH₃), 2.68 (1H, brs), 5.54 (1H, s, CH—C═N), 6.44-6.46 (1H, d, J=7.5 Hz, PhH₆), 6.79 (1H, s, CH═C—NH), 7.11-7.15 (2H, m, PhH_7,8), 7.34-7.37 (2H, d, J=7.2 Hz, Ph′H_2,6), 7.56-7.75 (5H, m, Ph′H_3,4,5, PyH₄, PhH₉), 8.16 (1H, s, PyH₆), 8.35 (1H, s, PyH₂). ¹³C NMR (100 MHz, CDCl₃) δ: 9.79, 18.45, 32.73, 89.49, 99.33, 114.13, 122.75, 127.63, 128.06, 128.51, 128.87, 129.67, 131.31, 131.89, 133.51, 134.87, 135.70, 136.32, 137.60, 141.18, 143.51, 144.97, 151.28, 152.66. HRMS (ESI-TOF⁺): [M+H]⁺ calcd for C₂₇H₂₄N₅: 418.2031: found: 418.2014.

TBI-097, 5-Phenyl-3-cyclopropylimino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 0.79-0.88 (4H, m), 2.70 (1H, brs), 4.00 (3H, s, CH₃), 5.55 (1H, s, CH—C═N), 6.43-6.46 (1H, d, J=7.8 Hz, PhH₆), 6.88-6.92 (2H, m, PhH₉, CH═C—NH), 7.08-7.17 (2H, m, PhH_7,8), 7.34-7.37 (2H, d, J=7.2 Hz, Ph′H_2,6), 7.60-7.75 (4H, m, PyH₅, Ph′H_3,4,5), 7.79-7.81 (1H, d, J=4.5 Hz, PyH₆), 7.83-7.85 (1H, d, J=7.8 Hz, PyH₄). ¹³C NMR (100 MHz, CDCl₃) δ: 9.90, 32.77, 53.67, 89.62, 100.09, 114.06, 116.81, 122.65, 124.83, 124.97, 127.54, 128.03, 128.93, 129.61, 131.28, 132.02, 134.82, 135.73, 137.64, 138.75, 142.63, 151.49, 152.87, 155.40. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₄N₅O: 434.1980; found: 434.1963.

TBI-098, 5-(4-Bromophenyl)-3-cyclobutylimino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.71-1.82 (2H, m), 2.01-2.08 (2H, m), (2H, m), 3.88-3.94 (1H, p, J=7.5 Hz), 5.10 (1H, s, CH—C═N), 6.47-6.49 (1H, d, J=7.5 Hz, PhH₆), 6.84 (1H, s, CH═C—NH), 7.12-7.32 (5H, m, PhH_7,8, Ph′H_2,6, PyH₅), 7.69-7.71 (1H, d, J=7.5 Hz, PyH₄), 7.77-7.79 (1H, d, J=8.1 Hz, PhH₉), 7.86-7.89 (2H, d, J=8.1 Hz, Ph′H_3,5), 8.34-8.35 (1H, d, J=3.9 Hz, PyH₆), 8.60 (1H, s, PyH₂). ¹³C NMR (100 MHz, CDCl₃) δ: 16.06, 31.96, 54.78, 90.55, 99.51, 113.95, 123.15, 123.66, 123.83, 127.88, 128.05, 128.40, 130.72, 131.28, 134.39, 134.66, 135.67, 136.51, 136.68, 143.60, 144.03, 144.41, 150.87, 151.13. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₁₇H₂₃BrN₅: 496.1136: found: 496.1114.

TBI-099, 5-(4-Bromophenyl)-3-(1-methylethyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) 1.09-1.11 (6H, d, J=6.3 Hz, CH(CH₃), 2.56 (3H, s, CH₃), 3.45-3.49 (1H, m, J=6.0 Hz, CH(CH₃)₂), 5.28 (1H, s, CH—C═N), 6.42-6.45 (1H, d, J=7.5 Hz, PhH₆), 6.71 OH, s, CH═C—NH), 7.09-7.25 (5H, m, PhH_7,8, Ph′H_2,6, PyH₅), 7.66-7.68 (2H, m, PyH₄, PhH₉), 7.84-7.87 (2H, d, J=8.4 Hz, Ph′H_3,5), 8.44 (1H, s, PyH₂). ¹³C NMR (100 MHz, CDCl₃) δ: 23.56, 23.82, 49.40, 89.60, 98.83, 113.84, 122.94, 123.16, 123.75, 127.53, 128.22, 129.47, 130.73, 131.36, 134.04, 134.68, 135.60, 136.63, 137.72, 143.77, 144.43, 150.37, 150.97, 153.36. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₅BrN₅: 498.1293; found: 498.1267.

TBI-100, 5-(4-Bromophenyl)-3-cyclopropylimino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 0.81-0.92 (4H, m,), 2.55 (3H, s, CH₃), 2.75 (1H, brs), 5.54 (1H, s, CH—C═N), 6.40-6.43 (1H, d, J=7.5 Hz, PhH₆), 6.65 (1H, s, CH═C—NH), 7.08-7.16 (3H, m, PhH₇, s, PyH₅) 7.24-7.27 (2H, J=8.4 Hz, Ph′H_2,6), 7.63-7.66 (2H, d, J=8.1 Hz, PyH₄, PhH₉), 7.84-7.87 (2H, d, J=8.4 Hz, Ph′H_3,5), 8.40-8.41 (1H, d, J=2.4 Hz, PyH₂). ¹³C NMR (100 MHz, CDCl₃) δ: 9.99, 23.82, 32.92, 89.45, 98.82, 113.80, 122.93, 123.18, 123.71, 127.54, 128.17, 129.68, 130.83, 131.51, 133.90, 134.57, 134.73, 135.72, 136.63, 143.90, 144.23, 151.20, 152.36, 153.52. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₃BrN₅: 496.1136; found: 496.11130.

TBI-501, 5-(4-Bromophenyl)-3-cyclobutylimino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.72-1.82 (2H, m), 2.02-2.08 (2H, m), 2.15-2.20 (2H, m), 2.56 (3H, s, CH₃), 3.88-3.93 (1H, p, J=7.8 Hz), 5.09 (1H, s, CH—C═N), 6.46-6.48 (1H, d, J=7.8 Hz, PhH₆), 6.71 (1H, s, CH═C—NH), 7.15-7.24 (5H, m, PhH_7,8, Ph′H_2,6, PyH₅), 7.67-7.70 (2H, d, J=8.1 Hz, PyH₄, PhH₉), 7.86-7.88 (2H, d, J=8.4 Hz, Ph′H_3,5), 8.46 (1H, s, PyH₂). HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₅BrN₅: 510.1293; found: 510.1267.

TBI-502, 5-(4-Bromophenyl)-3-cyclohexylimino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.18-1.44 (5H, m), 1.59-1.76 (5H, m), 2.55 (3H, s, CH₃), 3.06-3.13 (1H, m), 5.25 (1H, s, CH—C═N), 6.45-6.48 (1H, d, J=7.8 Hz, PhH₆), 6.70 (1H, s, CH═C—NH), 7.09-7.24 (5H, m, PhH_7,8, Ph′H_2,6, PyH₅), 7.66-7.69 (2H, m, PyH₄, PhH₉), 7.85-7.88 (2H, d, J=8.7 Hz, Ph′H_3,5), 8.44 (1H, d, J=2.4 Hz, PyH₂). ¹³C NMR (100 MHz, CDCl₃) δ: 23.81, 24.61, 25.84, 33.64, 57.91, 89.35, 98.81, 113.80, 122.91, 123.16, 123.63, 127.51, 128.21, 129.38, 130.73, 131.33, 134.07, 134.58, 134.67, 135.62, 136.64, 143.71, 144.43, 150.50, 151.04, 153.31. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₂₉BrN₅: 538.1606: found: 538.1593.

TBI-503, 5-(4-Bromophenyl)-3-(4-methoxycyclohexyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.18-0.28 (2H, q), 1.38-1.50 (2H, q), 1.69-1.72 (2H, d), 2.05-2.09 (2H, q), 2.56 (3H, s, CH₃), 3.08-3.24 (2H, m), 3.37 (3H, s, CH₃), 5.26 (1H, s, CH—C═N), 6.46-6.48 (1H, d, J=7.8 Hz, PhH₆), 6.72 (1H, s, CH═C—NH), 7.11-7.24 (5H, m, PhH_7,8, Ph′H_2,6, PyH₅), 7.66-7.70 (2H, m, PyH₄, PhH₉), 7.85-7.87 (2H, d, J=8.7 Hz, Ph′H_3,5), 8.44 (1H, d, J=2.1 Hz, PyH₂). ¹³C NMR (100 MHz, CDCl₃) δ: 23.82, 29.87, 31.15, 55.82, 57.25, 78.50, 89.08, 98.92, 113.90, 123.01, 123.17, 123.81, 127.65, 128.26, 129.43, 130.61, 131.30, 133.99, 134.61, 134.75, 135.62, 136.49, 143.75, 144.33, 150.86, 151.09, 153.42. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₁BrN₅O: 568.1711; found: 568.1703.

TBI-504, 5-(4-Bromophenyl)-3-(4-tetrahydropyranyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.62-1.69 (4H, m), 2.56 (3H, s, CH₃), 3.35-3.48 (3H, m), 3.95-4.00 (2H, m), 5.24 (1H, s, CH—C═N), 6.47-6.50 (1H, d, J=8.1 Hz, PhH₆), 6.73 (1H, s, CH═C—NH), 7.12-7.24 (5H, m, PhH_7,8, Ph′H_2,6, PyH₅), 7.66-7.70 (2H, m, PyH₄, PhH₉), 7.86-7.89 (2H, d, J=8.4 Hz, Ph′H_3,5), 8.45 (1H, d, J=2.4 Hz, PyH₂). ¹³C NMR (100 MHz, CDCl₃) δ: 23.84, 33.40, 54.32, 66.10, 88.91, 98.99, 113.94, 123.15, 123.21, 123.81, 127.73, 128.35, 129.60, 130.64, 131.17, 133.90, 134.66, 134.89, 135.64, 136.54, 143.83, 144.36, 150.70, 151.10, 153.59. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₇BrN₅O: 540.1398; found: 540.1380.

TBI-505, 5-Phenyl-3-cyclobutylimino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.62-1.77 (2H, m), 1.94-2.16 (4H, m), 3.79-3.90 (1H, p, J=7.5 Hz), 4.04 (3H, s, CH₃), 5.07 (1H, s, CH—C═N), 6.49-6.52 (1H, d, J=7.8 Hz, PhH₆), 6.89-6.94 (2H, m, PhH₉, CH═C—NH), 7.10-7.20 (2H, m, PhH_7,8), 7.31-7.34 (2H, d, J=7.5 Hz, Ph′H_2,6), 7.62-7.75 (4H, m, PyH₅, Ph′H_3,4,5), 7.80-7.81 (1H, d, J=4.8 Hz, PyH₆), 7.84-7.87 (1H, d, J=7.8 Hz, PyH₄). ¹³C NMR (100 MHz, CDCl₃) δ: 15.99, 31.96, 53.71, 54.88, 90.80, 100.28, 114.17, 116.81, 122.80, 124.76, 117.68, 128.15, 128.87, 129.70, 131.21, 131.71, 134.56, 135.69, 137.59, 138.75, 142.74, 151.63, 155.41. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₆N₅O: 448.2137; found: 448.2131.

TBI-506, 5-Phenyl-3-cyclobutylimino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.62-1.77 (2H, m), 1.95-2.18 (4H, m), 2.56 (3H, s, CH₃), 3.79-3.89 (1H, p, J=7.8 Hz), 5.08 (1H, s, CH—C═N), 6.50-6.53 (1H, d, J=7.8 Hz, PhH₆), 6.73 (1H, s, CH═C—NH), 7.10-7.20 (3H, m, PhH_7,8,9), 7.31-7.33 (2H, d, J=7.2 Hz, PhH_2,6), 7.63-7.75 (5H, m, Ph′H_3,4,5, PyH_4,5), 8.45 (1H, d, J=2.1 Hz, PyH₂). ¹³C NMR (100 MHz, CDCl₃) δ: 15.99, 23.83, 31.93, 54.84, 90.60, 98.89, 114.21, 122.88, 123.17, 127.60, 128.17, 128.82, 129.48, 129.73, 131.21, 131.51, 134.02, 134.61, 135,72, 137.59, 143.78, 144.30, 150.92, 151.43, 153.36. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₆N₅: 432.2188; found: 432.2188.

TBI-507, 5-(4-Bromophenyl)-3-(1-methylethyl)imino-2-(2-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.09-1.11 (6H, d, J=6.0 Hz, CH(CH₃)₂), 2.54 (3H, s, CH₃), 3.45-3.53 (1H, p, J=6.0 Hz, CH(CH₃)₂), 5.29 (1H, s, CH—C═N), 6.43-6.46 (1H, d, J=8.1 Hz, PhH₆), 6.57 (1H, s, CH═C—NH), 7.09-7.25 (5H, m, PhH_7,8, Ph′H_2,6, PyH₅), 7.65-7.68 (1H, d, J=0.8 Hz, PyH₄), 7.79-7.82 (1H, d, J=8.1 Hz, PhH₉), 7.85-7.88 (2H, d, J=8.4 Hz, Ph′H_3,5), 8.27-8.28 (1H, d, J=3.6 Hz, PyH₆). ¹³C NMR (100 MHz, CDCl₃) δ: 20.91, 23.59, 49.29, 89.01, 98.82, 113.85, 121.64, 122.96, 123.77, 127.55, 128.19, 129.17, 130,72, 131.37, 134.68, 134.79, 135.56, 136.62, 144.18, 150.29, 150.97, 152.27. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₅BrN₅: 498.1293; found: 498.1273.

TBI-508, 5-(4-Bromophenyl)-3-cyclohexylimino-2-(2-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.26-1.41 (5H, m), 1.60-1.76 (5H, m), 2.54 (3H, s, CH₃), 3.15 (1H, brs), 5.26 (1H, s, 6.46-6.48 (1H, d, J=7.5 Hz, PhH₆), 6.60 (1H, s, CH═C—NH), 7.10-7.25 (5H, m, PhH_7,8, Ph′H_2,6, PyH₅), 7.66-7.68 (1H, d, J=7.5 Hz, PyH₄), 7.81-7.83 (1H, d, J=8.4 Hz, PhH₉), 7.85-7.88 (2H, d, J=8.4 Hz, Ph′H_3,5), 8.26-8.27 (1H, d, J=3.6 Hz, PyH₆). ¹³C NMR (100 MHz, CDCl₃) δ: 20.93, 24,33, 25.89, 33.60, 57.35, 89.28, 98.82, 113.83, 121.64, 122.94, 123.67, 127.55, 128.20, 128.82, 130.72, 131.35, 134.61, 134.75, 134.80, 135.60, 136.63, 144.02, 144.09, 150.38, 151.04, 152.03. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₂₉BrN₅: 538.1606: found: 538.1603.

TBI-509, 5-(4-Bromophenyl)-3-(4-methoxycyclohexyl)imino-2-(2-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.19-1.30 (2H, q), 1.36-1.47 (2H, q), 1.71-1.74 (2H, d), 2.04-2.08 (2H, q), 2.58 (3H, s, CH₃), 3.11-3.25 (2H, m), 3.36 (3H, s, CH₃), 5.27 (1H, s, CH—C═N), 6.46-6.48 (1H, d, J=7.5 Hz, PhH₆), 6.59 (1H, s, CH═C—NH), 7.11-7.24 (5H, m, PhH_7,8, Ph′H_2,6, PyH₅), 7.66-7.69 (1H, d, J=7.5 Hz, PyH₄), 7.80-7.83 (1H, d, J=8.4 Hz, PhH₉), 7.85-7.87 (2H, d, J=8.7 Hz, Ph′H_3,5), 8.26-8.27 (1H, d, J=3.6 Hz, PyH₆). ¹³C NMR (100 MHz, CDCl₃) δ: 20.89, 29.57, 30.95, 55.80, 56.84, 89.04, 98, 94, 113.92, 121.66, 123.03, 123.83, 127.68, 128.24, 128.95, 130.60, 131.30, 134.63, 134.79, 135.57, 136.46, 143.98, 144.13, 150.85, 151.00, 152.05. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₁BrN₅O: 568.1711: found: 568.1691.

TBI-510, 5-Phenyl-3-(1-methylethyl)imino-2-(6-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.06-1.08 (6H, d, J=6.0 Hz, CH(CH₃)₂), 3.37-3.44 (1H, p, J=5.7 Hz, CH(CH₃)₂), 3.95 (1H, s, CH₃), 5.27 (1H, s, CH—C═NH), 6.46-6.48 (1H, d, J=8.1 Hz, PhH₆), 6.51 (1H, s, CH═C—NH), 6.76-6.79 (1H, d, J=8.7 Hz, PyH₅), 7.07-7.17 (2H, m, PhH_7,8), 7.32-7.34 (2H, d, J=7.5 Hz, Ph′H_2,6), 7.61-7.74 (5H, m, PhH₉), 8.14-8.15 (1H, d, J=2.4 Hz, PyH₂). ¹³C NMR (125 MHz, CDCl₃) δ: 23.52, 49.30, 53.60, 89.04, 98.04, 110.96, 114.08, 122.65, 127.20, 127.99, 128.85, 129.64, 130.34, 131.20, 131.60, 134.99, 135.10, 135.66, 137.76, 142.45, 145.99, 150.70, 151.03, 161.17. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₆N₅O: 436.2137; found: 436.2154.

TBI-511, 5-Phenyl-3-cyclopropylimino-2-(6-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 0.77-0.84 (4H, m), 2.70 brs), 3.95 (1H, s, CH₃), 5.54 (1H, s, CH—C═NH), 6.43-6.45 (2H, m, PhH₆, CH═C—NH), 6.76-6.78 (1H, d, J=8.4 Hz, PyH₅), 7.06-7.16 (2H, m, PhH_7,8), 7.34-7.36 (2H, d, J=7.5 Hz, Ph′H_2,6), 7.59-7.74 (5H, m, Ph′_3,4,5, PyH₄, PhH₉), 8.11 (1H, d, J=2.1 Hz, PyH₂). ¹³C NMR (125 MHz, CDCl₃) δ: 9.69, 32.75, 53.60, 89.39, 98.06, 111.01, 114.06, 122.64, 127.23, 127.93, 128.90, 129.59, 130.08, 131.25, 131.74, 134.81, 135.24, 135.73, 137.74, 142.56, 145.72, 151.22, 152.85, 161.25. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₄N₅O: 434.1980; found: 434.1969.

TBI-512, 5-Phenyl-3-cyclobutylimino-2-(6-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.65-1.76 (2H, m), 1.98-2.15 (4H, m), 3.82-3.87 (1H, p, J=8.1 Hz), 3.95 (3H, s, CH₃), 5.07 (1H, s, CH—C—NH), 6.50-6.52 (2H, m, PhH₆, CH═C—NH), 6.77-6.79 (1H, d, J=8.7 Hz, PyH₅), 7.09-7.19 (2H, m, PhH_7,8), 7.31-7.33 (2H, d, J=7.2 Hz, Ph′H_2,6), 7.62-7.75 (5H, m, Ph′H_{3,4, 5}, PyH₄, PhH₉), 8.15 (1H, d, J=2.4 Hz, PyH₂). ¹³C NMR (75 MHz, CDCl₃) δ: 15.99, 31.96, 53.62, 54.88, 90.57, 98.09, 111.04, 114.18, 122.81, 127.35, 128.04, 128.85, 129.69, 130.15, 131.19, 131.42, 134.56, 135.23, 135.70, 137.67, 142.57, 145.92, 150.92, 151.52, 161.26. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₆N₅O: 448.2137; found: 448.2125.

TBI-513, 5-Phenyl-3-cyclohexylimino-2-(6-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.07-1.41 (5H, m), 1.58-1.74 (5H, m), 3.00-3.06 (1H, m), 3.95 (3H, s, CH₃), 5.24 (1H, s, CH—C═NH), 6.50-6.52 (2H, m, PhH₆, CH═C—NH), 6.77-6.79 (1H, d, J=8.7 Hz, PyH₅), 7.07-7.17 (2H, m, PhH_7,8), 7.31-7.34 (2H, d, J=7.5 Hz, Ph′H_2,6), 7.61-7.74 (5H, m, Ph′H_3,4,5, PyH₄, PhH₉), 8.14 (1H, d, J=2.7 Hz, PyH₂). ¹³C NMR (75 MHz, CDCl₃) δ: 24.74, 25.84, 33.62, 53.62, 58.03, 89.33, 97.96, 102.96, 109.74, 110.96, 114,08, 122.62, 127.20, 127.98, 128.82, 129.55, 130.35, 131.16, 131.55, 134.90, 135.08, 135.66, 137.73, 142.42, 145.99, 150.85, 151.09, 154.65. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₃₀N₅O: 476.2444: found: 476.2453.

TBI-514, 5-Phenyl-3-(4-methoxycyclohexyl)imino-2-(6-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.06-1.17 (2H, q), 1.33-1.45 (2H, q), 1.66-1.70 (2H, d), 2.04-2.07 (2H, q), 2.99-3.05 (1H, m), 3.11-3.20 (1H, m), 3.35 (3H, s, CH₃), 3.95 (3H, s, CH₃), 5.21 (1H, s, CH—C═NH), 6.50-6.53 (2H, m, PhH₆, CH═C—NH), 6.76-6.79 (1H, d, J=8.7 Hz, PyH₅)^,7.09-7.18 (2H, m, PhH_7,8), 7.30-7.32 (2H, d, J=7.5 Hz, Ph′H_2,6), 7.60-7.73 (5H, m, Ph′H_3,4,5, PyH₄, PhH₉), 8.13 (1H, d, J=2.1 Hz, PyH₂). ¹³C NMR (75 MHz, CDCl₃) δ: 30.08, 31.18, 53.62, 55.85, 57.51, 78.60, 89.10, 98.05, 110.98, 114.14, 122.71, 127.34, 128.01, 128.70, 129.74, 130.19, 131.17, 131.45, 134.94, 135.08, 135.63, 137.57, 142.42, 145.84, 150.89, 151.49, 161.16. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₂N₅O₂: 506.2550; found: 506.2552.

TBI-515, 5-Phenyl-3-(4-tetrahydropyranyl)imino-2-(6-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.61-1.67 (4H, m), 3.29-3.40 (3H, m), 3.94-3.96 (5H, m), 5.23 (1H, s, CH—C═NH), 6.50-6.53 (2H, m, PhH₆, CH═C—NH), 6.77-6.80 (1H, d, J=9.0 Hz, PyH₅), 7.12-7.17 (2H, m, PhH_7,8), 7.31-7.34 (2H, d, J=72 Hz, Ph′H_2,6), 7.62-7.75 (5H, m, Ph′H_3,4,5, PyH₄, PhH₉), 8.15 (1H, d, J=2.7 Hz, PyH₂). ¹³C NMR (75 MHz, CDCl₃) δ: 33.41, 53.63, 54.47, 66.24, 88.91, 98.19, 111.04, 114.20, 122.87, 127.42, 128.12, 128.74, 129.71, 130.15, 131.22, 131.40, 135.14, 135.69, 137.67, 142.51, 145.88, 150.77, 151.41, 161.27. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂H₂₈N₅O₂: 478.2237; found: 478.2249.

TBI-516, 5-(4-Bromophenyl)-3-(1-methylethyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.10-1.12 (6H, d, J=6.0 Hz, CH(CH₃)₂), 3.45-3.49 (1H, p, J=6.0 Hz, CH(CH₃)₂), 4.03 (3H, s, CH₃), 5.28 (1H, s, CH—C═N), 6.42-6.44 (1H, d, J=8.1 Hz, PhH₆), 6.89-6.93 (2H, m, PyH₅, CH═C—NH), 7.09-7.19 (2H, m, PhH_7,8), 7.22-7.25 (2H, d, J=8.4 Hz, Ph′H_2,6), 7.67-7.69 (1H, d, J=7.8 Hz, PyH₄), 7.80-7.87 (4H, m, Ph′H_3,5, Ph′H₉, PyH₆). ¹³C NMR (100 MHz, CDCl₃) δ: 23.56, 49.39, 53.71, 89.25, 100.08, 113.79, 116.78, 122.87, 123.71, 124.84, 124.93, 127.60, 128,19, 130,77, 131,54, 134.67, 135.57, 136.62, 138.83, 142.92, 150.55, 151.23, 155.49. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂H₂₅BrN₅O: 514.1242; found: 514.1219.

TBI-517, 5-(4-Bromophenyl)-3-cyclohexylimino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.22-1.48 (5H, m), 1.59-1.79 (5H, m), 3.12-3.17 (1H, m), 4.03 (3H, s, CH₃), 5.25 (1H, s, CH—C═N), 6.44-6.48 (1H, d, J=7.8 Hz, PhH₆), 6.89-6.93 (2H, m, PyH₅, CH═C—NH), 7.10-7.19 (2H, m, PhH_7,8), 7.22-7.25 (2H, d, J=8.4 Hz, Ph′H_2,6), 7.67-7.70 (1H, d, J=7.8 Hz, PyH₄), 7.79-7.88 (4H, m, Ph′H_3,5, PyH₆). ¹³C NMR (100 MHz, CDCl₃) δ: 24.18, 25.99, 33.52, 53.70, 57.27, 89.48, 100.12, 113.77, 116.80, 122.86, 123.61, 124.52, 124.95, 127.60, 128.20, 130.77, 131.52, 134.59, 134.66, 135.60, 136.63, 138.64, 142.85, 150.54, 151.32, 155.38, HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₂₉BrN₅O: 554.1555; found: 554.1561.

TBI-518, 5-(4-Bromophenyl)-3-(4-tetrahydropyranyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

mp: 225-227□. ¹H NMR (300 MHz, CDCl₃) δ: 1.58-1.72 (4H, m), 3.43-3.56 (3H, m), 3.99-4.06 (5H, m), 5.25 (1H, s, CH—C═N), 6.46-6.49 (1H, d, J=8.1 Hz, PhH₆), 6.90-6.95 (2H, m, PyH₅, CH═C—NH), 7.12-7.25 (4H, m, PhH_7,8, Ph′H_2,6), 7.70-7.73 (1H, d, J=7.5 Hz, PyH₄), 7.81-7.91 (4H, m, PhH₉, Ph′H_3,5, PyH₆). ¹³C NMR (100 MHz, CDCl₃) δ: 33.29, 53.26, 53.76, 65.56, 88.97, 100.30, 113.92, 116.83, 123.11, 123.81, 124.34, 124.84, 127.81, 128.33, 129.35, 129.87, 130.67, 131.35, 134.68, 134.92, 135.62, 136.51, 138.74, 142.63, 150.96, 151.09, 155.30. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₇BrN₅O₂: 556.1348: found: 556.1358.

TBI-519, 5-(4-Bromophenyl)-3-cyclopropylimino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

mp: 217-218□. ¹H NMR (300 MHz, CDCl₃) δ: 0.83-0.92 (4H, m), 2.75 (1H, brs), 4.05 (3H, s, CH₃), 5.54 (1H, s, CH—C═N), 6.40-6.42 (1H, d, J=7.8 Hz, PhH₆), 6.87-6.92 (2H, m, PyH₅, CH═C—NH), 7.08-7.18 (2H, m, PhH_7,8), 7.24-7.27 (2H, d, J=8.4 Hz, Ph′H_2,6), 7.65-7.67 (1H, d, J=7.5 Hz, PyH₄), 7.79-7.87 (4H, m, PhH₉, Ph′H_3,5, PyH₆). ¹³C NMR (100 MHz, CDCl₃) δ: 10.11, 32.90, 53.69, 89.66, 100.07, 113.78, 116.82, 122.89, 123.71, 124.71, 125.13, 127.62, 128.16, 130.86, 131.66, 134.53, 134.74, 135.73, 136.60, 138.91, 142.63, 151.42, 152.50, 155.43. HRMS (ESI-TOF⁺): m/z [M+H]⁺ If calcd for C₂₇H₂₃BrN₅O: 512.1085; found: 512.1075.

TBI-520, 5-(4-Bromophenyl)-3-cyclobutylimino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

mp: >250□. ¹H NMR (300 MHz, CDCl₃) δ: 1.70-1.82 (2H, m), 2.00-2.24 (4H, m), 3.85-3.96 (1H, p, J=8.1 Hz), 4.00 (3H, s, CH₃), 5.09 (1H, s, CH—C═N), 6.45-6.48 (1H, d, J=7.5 Hz, Ph′H₆), 6.89-6.93 (2H, m, PyH₅, CH═C—NH), 7.11-7.18 (2H, m, PhH_7,8), 7.21-7.24 (2H, d, J=8.7 Hz, Ph′H_2,6), 7.68-7.71 (1H, d, J=7.5 Hz, PyH₄), 7.81-7.88 (4H, m, PhH₉, Ph′H_3,5, PyH₆). ¹³C NMR (100 MHz, CDCl₃) δ: 16.06, 32.00, 53.73, 54.85, 90.75, 100.26, 113.87, 116.80, 123.02, 123.74, 124.76, 124.84, 127.73, 128.27, 130.79, 131.38, 134.28, 134.61, 135.66, 136.56, 138.87, 142.76, 151.14, 151.39, 155.43. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₅N₅OBr: 526.1236; found: 526.1244.

TBI-521, 5-(4-Bromophenyl)-3-(4-methoxycyclohexyl)imino-2-(2-ethoxy-3-pyridyl)amino-3,5-dihydrophenazine

mp: 234-236□. ¹H NMR (300 MHz, CDCl₃) δ: 1.23-1.32 (2H, q), 1.39-1.49 (2H, q), 1.71-1.74 (2H, d), 2.04-2.09 (2H, q), 3.12-3.18 (1H, m), 3.22-3.28 (1H, m), 3.36 (3H, s, CH₃), 4.02-4.05 (4H, m), 5.26 (1H, s, CH—C═N), 6.45-6.48 (1H, d, J=7.51 Hz. PhH₆), 6.89-6.93 (2H, m, PyH₅, CH═C—NH), 7.13-7.24 (4H, m, PhH_7,8, PhH_2,6), 7.68-7.71 (1H, d, J=6.9 Hz, PyH₄), 7.80-7.87 (4H, m, PhH₉, Ph′H_3,5, PyH₆). ¹³C NMR (100 MHz, CDCl₃) δ: 29.35, 30.69, 53, 71, 55.79, 56.73, 78.24, 89.24, 100.22, 113.87, 116.84, 122.96, 123.79, 124.61, 124.86, 127.72, 128.26, 129.88, 130.65, 131.47, 134.63, 134.73, 135.61, 136.47, 138.74, 142.72, 151.18, 155.36. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₁N₅O₂Br: 584.1655; found: 584.1667.

TBI-522, 5-(3-Fluorophenyl)-3-(1-methylethyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

mp: 164-166□, ¹H NMR (300 MHz, CDCl₃) δ: 1.14 (6H, brs), 3.42-3.48 (1H, m), 5.28 (1H, s), 6.46-6.48 (1H, d, J=8.1 Hz), 6.83 (1H, s), 7.09-7.17 (4H, m), 7.29-7.39 (2H, m), 7.68-7.79 (3H, m), 8.32-8.33 (1H, d, J=5.2 Hz), 8.58 (1H, s). ¹³NMR (100 MHz, CDCl₃) δ: 23.48, 23.59, 49.40, 89.11, 99.44, 113.85, 116.40, 116.62, 117.01, 117.22, 123.03, 123.63, 124.79, 127.77, 127.95, 128.31, 131.32, 132.62, 132.71, 134.70, 136.82, 138.88, 143.68, 143.97, 144.28, 150.38, 150.95. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₆H₂₃FN₃: 424.1937; found: 424.1921.

TBI-523, 5-(3-Fluorophenyl)-3-(1-methylethyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.11 (6H, hr s), 3.42-3.50 (1H, m), 4.04 (3H, s), 5.29 (1H, s), 6.46-6.48 (1H, d, J=8.1 Hz), 6.93 (2H, brs), 7.10-7.20 (4H, m), 7.34-7.40 (1H, t, J=8.1 Hz), 7.69-7.76 (2H, m), 7.81-7.86 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 23.47, 49.39, 53.70, 89.28, 100.10, 113.77, 116.45, 116.67, 116.78, 116.93, 117.14, 122.89, 124.84, 124.91, 127.62, 128.19, 131.42, 132.58, 132.67, 134.58, 135.54, 138.81, 138.94, 142.90, 150.61, 151.25, 155.49, 162.95, 165.44. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₅FN₅O: 454.2038; found: 454.2043.

TBI-524, 5-(3-Fluorophenyl)-3-(4-tetrahydropyranyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.67 (4H, brs), 3.41-3.50 (3H, m), 4.01-4.04 (5H, m), 5.26 (1H, s), 6.49-6.52 (1H, d, J=8.1 Hz), 6.90-6.94 (1H, m), 6.97 (1H, s), 7.09-7.22 (4H, m), 7.36-7.41 (1H, t, J=8.7 Hz), 7.69-7.76 (2H, m), 7.81-7.86 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 33.26, 33.36, 53.46, 53.75, 65.66, 88.99, 100.31, 113.89, 116.39, 116.61, 116.82, 116.99, 117.20, 123.12, 124.36, 124.75, 124.84, 127.83, 128.32, 131.24, 132.61, 132.70, 134.78, 135.59, 138.74, 138.92, 142.63, 150.98, 151.17, 155.31, 162.95, 165.44. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₇FN₅O₂: 496.2143; found: 496.2152.

TBI-525, 5-(3,4-Difluorophenyl)-3-ethylethyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.10-1.14 (6H, t, J=6.9 Hz), 3.48-3.52 (1H, m, J=6.6 Hz), 5.29 (1H, s, CH—C═N), 6.44-6.47 (1H, d, J=8.1 Hz), 6.82 (1H, s, CH═C—NH), 7.13-7.32 (5H, m), 7.50-7.56 (1H, dd, J=9.0 Hz), 7.67-7.70 (1H, d, J=7.8 Hz), 7.76-7.79 (1H, d, J=8.4 Hz), 8.33 (1H, d, J=4.5 Hz), 8.59 (1H, d, J=2.1 Hz). ¹³C NMR (100 MHz, CDCl₃) δ: 23.50, 23.63, 49.48, 89.06, 99.44, 113.62, 118.63, 118.80, 119.89, 120.08, 123.16, 123.62, 125.72, 127.81, 127.99, 128.41, 131.32, 133.63, 134.77, 135,53, 136.70, 143.67, 144.00, 144.37, 150.21, 150.96. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₆H₁₂F₂N₅: 442.1838; found: 442.1844.

TBI-526, 5-(3,4-Difluorophenyl))-3-cyclobutylimino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.74-1.83 (2H, m), 2.02-2.21 (4H, m), 3.90-3.96 (1H, p, J=7.8 Hz), 5.10 (1H, s, CH—C═N), 6.47-6.49 (1H, d, J=6.9 Hz), 6.82 (1H, s, CH═C—NH), 7.14-7.33 (5H, m), 7.51-7.60 (1H, dd, J=9.0 Hz), 7.69-7.71 (1H, d, J=7.5 Hz), 7.76-7.79 (1H, d, J=8.1 Hz), 8.34-8.35 (1H, d, J=4.5 Hz), 8.60 (1H, d, J=2.1 Hz). ¹³C NMR (100 MHz, CDCl₃) δ: 16.07, 32.00, 54.83, 90.55, 99,52, 113.70, 118.65, 118.83, 119.85, 120.03, 123.31, 123.66, 125.74, 127.94, 128.10, 128.49, 131.18, 133.61, 134.35, 135.62, 136.60, 143.60, 144.05, 144.49, 149.64, 150.50, 150.64, 150.90, 151.04, 152.28, 153.03, 153.17, HRMS m/z [M+H]⁺ calcd for C₂₇H₂₂F₂N₅: 454.1838; found: 454.1852.

TBI-527, 5-(3,4-Difluorophenyl)-3-cyclohexylimino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.25-1.41 (5H, m), 1.62-1.78 (5H, m), 3.10-3.17 (1H, m), 5.27 (1H, s, CH—C═N), 6.46-6.48 (1H, d, J=7.8 Hz), 6.82 (1H, s, CH═C—NH), 7.15-7.32 (5H, m), 7.51-7.60 (1H, dd, J=8.7 Hz), 7.67-7.70 (1H, d, J=7.2 Hz), 7.76-7.79 (1H, d, J=8.1 Hz), 8.33-8.34 (1H, d, J=4.8 Hz), 8.58 (1H, s). ¹³C NMR (100 MHz, CDCl₃) δ: 24.54, 24.62, 25.79, 33.60, 33.71, 57.96, 89.30, 99.44, 113.60, 118.66, 118.84, 119.78, 119.96, 123.15, 123.62, 125.72, 127.79, 127.91, 128.41, 131.31, 133.65, 134.68, 135.57, 136.74, 143.69, 143.97, 144.33, 149.71, 150.31, 150.50, 151.03, 153.17. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₆F₂N₅: 482.2151; found: 482.2152.

TBI-528, 5-(3,4-Difluorophenyl)-3-(1,3-dimethoxyisopropyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 3.29 (6H, s), 3.35-3.43 (2H, m), 3.53-3.58 (2H, m), 3.70-3.76 (1H, m,), 5.50 (1H, s, CH—C═N), 6.47-6.50 (1H, d, J=7.8 Hz), 6.84 (1H, s, CH═C—NH), 7.12-7.32 (5H, m), 7.48-7.60 (1H, dd, J=8.4 Hz), 7.70-7.72 (1H, d, J=7.2 Hz), 7.76-7.79 (1H, d, J=8.4 Hz), 8.33-8.35 (1H, d, J=4.5 Hz), 8.58 (1H, d, J=2.1 Hz). ¹³C NMR (100 MHz, CDCl₃) δ: 58.75, 59.07, 59.11, 74.50, 74.62, 90.31, 99.61, 113.74, 118.60, 118.78, 119.81, 119,99, 123.26, 123.63, 125.64, 127.99, 128.16, 128.52, 131.25, 133.49, 134.65, 135.55, 136.58, 143.57, 144.14, 144.48, 149.66, 149.78, 150.50, 150.71, 152.18, 153.03, 153.16, 153.26. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₆F₂N₅O₂: 502.2049; found: 502.2042.

TBI-529, 5-(3,4-Difluorophenyl)-3-(1-methylethyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.10-1.15 (6H, t, J=6.9 Hz), 3.45-3.53 (1H, m, J=6.3 Hz), 4.04 (3H, s), 5.28 (1H, s, CH—C═NH), 6.42-6.45 (1H, d, J=7.5 Hz), 6.89-6.93 (2H, m), 7.13-7.25 (4H, m), 7.49-7.59 (1H, dd, J=9.0 Hz), 7.67-7.70 (1H, d, J=7.2 Hz), 7.81-7.84 (2H, m), 8.92 (1H, s). ¹³C NMR (100 MHz, CDCl₃) δ: 23.48, 23.62, 49.46, 53.71, 89.23, 100.10, 113.55, 116.78, 118.68, 118.86, 119.86, 120.04, 123.05, 124.77, 124.96, 125.75, 127.66, 128.29, 131.41, 133.69, 134.67, 135.54, 138.90, 142.90, 149.59, 149.71, 150.47, 150.67, 151.23, 152.11, 152.23, 153.06, 153.19, 155.49. HRMS (ESI-TOF⁺): [M+H]⁺ calcd for C₂₇H₂₄F₂N₅O: 472.1943; found: 472.1937.

TBI-530, 5-(3,4-Difluorophenyl)-3-cyclobutylimino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.70-1.82 (2H, m), 2.03-2.20 (41), m), 3.90-3.95 (1H, p, J=7.8 Hz), 4.04 (3H, s), 5.08 (1H, s, CH—C═N), 6.45-6.47 (1H, d, J=7.5 Hz), 6.89-6.93 (2H, m), 7.12-7.23 (4H, m), 7.50-7.59 (1H, dd, J=8.7 Hz), 7.68-7.70 (1H, d, J=7.5 Hz), 7.82-7.84 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 16.07, 32.04, 53.73, 54.87, 90.74, 100.26, 113.63, 116.78, 118.69, 118.86, 119.81, 119.99, 123.19, 124.68, 124.86, 125.77, 127.79, 128.35, 131.26, 133.60, 134.24, 135.61, 138.94, 142.74, 150.48, 150.62, 151.14, 151.31, 155.43. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₄F₂N₅O: 484.1943; found: 484.1933.

TBI-531, 5-(3,4-Difluorophenyl)-3-cyclohexylimino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.23-1.79 (10H, m), 3.14-3.20 (1H, m), 4.03 (3H, s), 5.26 (1H, s, CH—C═N), 6.43-6.46 (1H, d, J=7.5 Hz), 6.88-6.93 (2H, m), 7.11-7.25 (4H, m), 7.49-7.58 (1H, dd, J=8.7 Hz), 7.67-7.70 (1H, d, J=7.5 Hz), 7.80-7.84 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 24.21, 25.95, 33.50, 33.61, 53.71, 57.38, 89.42, 100.14, 113.53, 116.80, 118.71, 118.89, 119.75, 119.94, 123.03, 124.54, 124.89, 125.77, 127.65, 128.29, 131.41, 133.67, 134.62, 135.56, 138.71, 142.84, 149.56, 150.42, 151.34, 152.19, 153.02, 155.38. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₂₈F₂N₅O: 512.2256: found: 512.7263.

TBI-532, 5-(3,4-Difluorophenyl)-3-(4-tetrahydropyranyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.65-1.68 (4H, m), 3.46-3.55 (3H, m), 4.05 (5H, m), 5.25 (1H, s, CH—C═N), 6.45-6.48 (1H, d, J=9.0 Hz), 6.90-6.95 (2H, m), 7.13-7.24 (4H, m), 7.51-7.60 (1H, dd, J=9.0 Hz, 8.7 Hz), 7.70-7.72 (1H, d, J=7.5 Hz), 7.81-7.85 (2H, m), 9.08 (1H, s). HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₆F₂N₅O₂: 514.2049; found: 514.2042.

TBI-300, 5-(4-Methylphenyl)-3-(1-methylethyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.05 (6H, d, J=6.3 Hz, —CH(CH₃)₂), 2.58 (3H, s, —CH₃), 3.41 (1H, m, —CH(CH₃)₂), 5.38 (1H, s, 4-H), 6.50 (1H, d, J=7.8 Hz, 6-H), 6.85 (1H, s, 1-H), 7.13 (2H, q, J₁=8.1 Hz, J₂=7.8 Hz, 7-H, 8-H), 7.20 (2H, d, J=7.5 Hz, 2″-H, 6″-H), 7.28 (1H, d, J=8.1 Hz, 9-H), 7.50 (2H, J=7.5 Hz, 3″-H, 5″-H), 7.68 (1H, d, J=7.2 Hz, 4″-H), 7.78 (1H, d, J=7.8 Hz, 5″-H), 7.32 (1H, d, J=4.2 Hz, 6″-H), 8.58 (1H, s, 2′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 21.43, 23.51, 49.21, 89.03, 99.43, 114.29, 122.72, 123.60, 127.59, 127.81, 128.13, 128.37, 131.83, 134.85, 135.19, 135.69, 137.03, 139.74, 143.66, 143.91, 144.10, 150.63, 150.91. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₆N₅: 420.2157; found: 420.2156.

TBI-301, 5-(4-Methylphenyl)-3-(4-methoxycyclohexyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.12 (2H, m, —CH₂—CH₂—OCH₃), 1.41 (2H, m, —C₂CH₂—OCH₃), 1.70 (2H, m, CH—CH₂), 2.09 (2H, m, CH—CH₂), 2.58 (3H, s, —CH₃), 3.05 (1H, m, —CH—OCH₃), 3.18 (1H, m, —N—CH), 3.18 ((3H, s, —OCH₃), 5.35 (1H, s, 4-H), 6.55 (1H, J=7.2 Hz, 6-H), 6.87 (1H, s, 1-H), 7.14 (2H, q, J=8.1 Hz, J=7.2 Hz, 7-H, 8-H), 7.19 (2H, d, J=7.8 Hz, 2″-H, 6″-H), 7.28 (1H, d, J=8.1 Hz, 9-H), 7.50 (2H, d, J=7.8 Hz, 3″-H, 5″-H), 7.60 (1H, d, 6.6 Hz, 4′-H), 7.69 (1H, d, J=8.1 Hz, 5′-H), 8.32 (1H, d, J=4.2 Hz, 6′-H), 8.57 (1H, s, 2′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 21.44, 29.97, 31.09, 55.87, 57.19, 78.57, 89.08, 99.58, 114.58, 122.81, 123.62, 127.77, 128.28, 131.76, 134.73, 135.17, 135.71, 136.87, 139.94, 143.51, 143.89, 144.18, 150.81, 151.36. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₂N₅O: 490.2589: found: 490.2587.

TBI-302, 5-(4-Methylphenyl)-3-(2-morpholinoethyl)imino-2-(3-pyridyl)amino-3,5-dihydro-phenazine

¹H NMR (300 MHz, CDCl₃) δ: 2.20-2.30 (8H, m, —CH₂CH₂OCH₂CH₂—), 2.70 (2H, CH₂CH₂), 3.25 (2H, CH₂CH₂), 3.65 (3H, s, —CH₃), 5.35 (1H, s, 4-H), 6.51 (1H, d, J=7.2 Hz, 6-H), 6.85 (1H, s, 1-H), 7.10 (2H, q, J=8.1 Hz, J=7.2 Hz, 7-H, 8-H), 7.19 (2H, d, J=7.8 Hz, 2″-H, 6″-H), 7.32 (1H, m, 9-H), 7.51 (2H, d, J=7.8 Hz, 3″-H, 5″-H), 7.71 (1H, d, J=5.4 Hz, 4′-H), 7.79 (1H, d, J=6.9 Hz, 5′-H), 8.32 (1H, 6′-H), 8.57 (1H, s, 2″-H). ¹³C NMR (100 MHz, CDCl₃) δ: 21.41, 54.07, 66.93, 88.95, 99.58, 114.52, 123.04, 123.68, 127.91, 128.21, 132.02, 124.76, 135.25, 135.74, 136.74, 139.94, 143.33, 143.92, 144.35, 152.99. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₃₁N₆O: 491.2583; found: 491.2582.

TBI-303, 5-(4-Methylphenyl)-3-(4-tetrahydropyranyl)imino-2-(3-pyridinyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.63 (4H, m, —CH₂—CH—CH₂—), 2.57 (3H, s, —CH₃), 3.29 (1H, m-—CH₂—CH—CH₂—), 3.40 (2H, m, —CH₂—O), 3.99 (2H, m, —CH₂—O), 5.27 (1H, s, 4-H), 6.58 (1H, d, J=7.5 Hz, 6-H), 6.87 (1H, s, 1-H), 7.15 (2H, q, J=7.8 Hz, J=7.5 Hz, 7-H, 8-H), 7.19 (2H, d, 8.1 Hz, 2″-H, 6″-H), 7.35 (1H, d, J=7.8 Hz, 9-H), 7.51 (2 d, J=8.1 Hz, 3″-H, 5″-H), 7.68 (1H, d, J=6.91 Hz, 4′-H), 7.81 (1H, d, J=8.4 Hz, 5′-H), 8.37 (1H, d, J=3.9 Hz, 6′-H), 8.60 (1H, s, 2″-H), ¹³C NMR (100 MHz, CDCl₃) δ: 21.41, 33.40, 54.32, 66.21, 88.96, 99.63, 114.38, 122.92, 123.67, 127.86, 127.93, 128.35, 131.81, 134.84, 135.31, 135.72, 136.80, 139.90, 143.57, 143.97, 144.35, 150.74, 151.37. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₈N₅O: 462.2584; found: 462,2582.

TBI-104, 5-(4-Methylphenyl)-3-(N-methyl-4-piperidyl)imino-2-(3-pyridinyl)amino-3,5-dihydro-phenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.66 (4H, m, —CH₂CH—CH₂—), 2.20 (2H, m, —CH₂—N), 2.27 (3H, s, N—CH₃), 2.53 (3H, s, —CH₃), 2.78 (2H, m, —CH₂—N), 3.11 (1H, m-CH₂—CH—CH₂—), 5.53 (1H, s, 4-H), 6.57 (1H, d, J=7.2 Hz, 6-H), 6.83 (1H, 1-H), 7.13 (2H, J=7.2 Hz, J=8.4 Hz, 7-H, 8-H), 7.20 (2H, d, J=8.1 Hz, 2″-H, 6″-H), 7.30 (1H, d, J=8.4 Hz, 9-H), 7.52 (2H, d, J=7.2 Hz, 3″-H, 5″-H), 7.70 (1H, d, J=6.6 Hz, 4″-H), 7.78 (1H, d, J=8.4 Hz, 5″-H), 8.33 (1H, d, J=4.8 Hz, 6″-H), 8.59 (1H, s, ¹³C NMR (100 MHz, CDCl₃) δ: 21.41, 26.39, 32.46, 46.28, 53.86, 89.12, 99.61, 114.45, 123.68, 127.92, 128.29, 131.82, 134.79, 135.25, 136.85, 143.50, 144.02, 144.34, 151.38. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₃₁N₆: 475.2548; found: 475.2546.

TBI-305, 5-(4-Methylphenyl)-3-(N-isobutyl-4-piperidyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 0.89 (6H, d, J=6.9 Hz, (CH₃)₂—CH—), 1.58-1.99 (8H, m, —CH₂—CH₂—CH—CH₂—CH₂—), 2.07 (2H, d, J=5.4 Hz, CH₂—CH), 2.55 (3H, s, —CH₃), 2.78 (1H, m, (CH₃)₂—CH—), 3.11 (1H, m, N—CH—CH₂—), 5.31 (1H, s, 4-H), 6.55 (1H, d, J=7.8 Hz, 6-H), 6.88 (1H, s, 1-H), 7.14 (2H, m, 7-H, 8-H), 7.20 (2H, J=7.8 Hz, 2″-H, 6″-H), 7.30 (1H, m, 9-H), 7.51 (2H, d, J=7.8 Hz, 3″-H, 5″-H), 7.69 (1H, d, J=6.0 Hz, 4′-H), 7.78 (1H, d, J=6.0 Hz, 5′-H), 8.28 (1H, d, J=4.5 Hz, 6′-H), 8.58 (1H, s, 2″-H). ¹³C NMR (100 MHz, CDCl₃) δ: 20.98, 21.40, 25.72, 31.85, 32.72, 52.43, 55.78, 67.11, 89.16, 99.47, 109.76, 114.34, 122.79, 123.64, 127.72, 128.35, 131.35, 135.79, 135.79, 136.95, 139.77, 143.87, 144.14, 151.12, 155.00. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₁₃H₃₇N₆: 517.3156; found: 517.3157.

TBI-306, 5-(4-Methylphenyl)-3-cyclohexylimino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.13-1.75 (10H, m, —CH₂—CH₂—CH₂—CH₂—CH₂—), 2.53 (6H, s-CH₃, py-CH₃), 3.06 (1H, m, —CH₂—CH—CH₂—), 5.28 (1H, s, 4-H), 6.53 (1H, d, J=7.5 Hz, 6-H), 6.72 (1H, s, 1-H), 7.08-7.16 (3H, m, 7-H, 8-H, 9-H), 7.19 (2H, d, J=7.8 Hz, 2″-H, 6″-H), 7.50 (2H, d, J=7.8 Hz, 3″-H, 5″-H), 7.67 (1H, d, 0.7 Hz, 4′-H), 7.61 (1H, d, J=2.7 Hz, 5′-H), 8.45 (1H, s, 2′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 21.36, 23.80, 24.68, 25.86, 33.58, 57.81, 89.32, 98.79, 114.21, 122.21, 123.12, 127.39, 128.04, 128.39, 129.28, 131.69, 134.28, 134.93, 135.05, 135.71, 139.65, 143.67, 144.41, 120.83, 151.03, 153.11. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₂N₅: 474.3848; found: 474.3846.

TBI-307, 5-(4-Methylphenyl)-3-(N-cyclopentyl-4-piperidyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.35-2.15 (16H, m, —CH₂—CH₂—N—CH₂—CH₂—, —CH₂—CH₂—CH₂—CH₂—), 2.52 (3H, s, —CH₃), 2.91 (1H, m, —CH₂—CH—CH₂—), 3.12 (1H, m, N—CH—CH₂), 5.28 (1H, s, 4-H), 6.55 (1H, d, J=6.6 Hz, 6-H), 6.89 (1H, s, 1-H), 7.12 (2H, m, 7-H, 8-H), 7.19 (2H, d, J=7.8 Hz, 2″-H, 6″-H), 7.31 (1H, m, 9-H), 7.52 (2H, d, J=7.8 Hz, 3″-H, 5″-H), 7.62 (1H, d, J=5.4 Hz, 4′-H), 7.80 (1H, d, 6.9 Hz, 5′-H), 8.32 (1H, d, J=3.9 Hz, 6′-H), 8.57 (1H, s, 2′-H), ¹³C NMR (100 MHz, CDCl₃) δ: 21.41, 24.15, 30.64, 32.69, 50.81, 67.71, 89.19, 99.56, 114.38, 122.85, 123.67, 127.77, 128.28, 131.83, 135.28, 136.86, 143.50, 143.93, 150.04. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₅₄H₃₇N₆: 529.2046; found: 529.3054.

TBI-308, 5-(4-Methylphenyl)-3-(1-methylethyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.19 (6H, d, J=6.3 Hz, —CH(CH₃—)₂), 2.54 (3H, s, —CH₃), 3.43 (1H, m, —CH(CH₃)₂), 4.03 (3H, s, —OCH₃), 5.32 (1H, s, 4-H), 6.48 (1H, d, J=7.8 Hz, 6-H), 6.90 (1H, J=8.1 Hz, 9-H), 6.92 (1H, s, 1-H), 7.12 (2H, m, 7-H, 8-H), 7.20 (2H, d, 7.8 Hz, 2″-H, 6″-H), 7.49 (2H, d, J=7.8 Hz, 3″-H, 5″-H), 7.68 (1H, d, J=7.2 Hz, 4′-H), 7.80 (1H, d, J=5.1 Hz, 5′-H), 7.85 (1H, d, J=7.8 Hz, 6′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 21.42, 23.51, 49.23, 53, 68, 89.21, 100.14, 114.19, 116.79, 122.56, 124.88, 124.99, 127.49, 128.03, 128.44, 131.80, 132.07, 134.90, 135.06, 138.67, 139.65, 142.90, 150.86, 151.26, 155.49. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₈N₅O: 450.2334; found: 450.2330.

TBI-309, 5-(4-Methylphenyl)-3-(4-methoxycyclohexyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.21 (2H, m, —CH₂—CH₂—), 1.42 (2H, m, —CH₂—CH₂—), 1.70 (2H, m, —CH—CH₂—), 2.08 (2H, m, —CH—CH₂—), 2.58 (3H, s, —CH₃), 3.10 (1H, m, —CH₂—CH—CH₂—), 3.24 (1H, m, —CH₂—CH—CH₂—), 3.38 (3H, s, —OCH₃), 4.05 (3H, s, —OCH₃), 5.23 (1H, s, 4-H), 6.52 (1H, d, J=6.2 Hz, 6-H), 6.91 (1H, m, 9-H), 6.95 (1H, s, 1-H), 7.12 (2H, m, 7-H, 8-H), 7.17 (2H, d, J=8.1 Hz, 2″-H, 7.49 (2H, d, J=8.1 Hz, 3″-H, 5″-H), 7.68 (1H, d, J=8.1 Hz, 4′-H), 7.80 (1H, d, J=6.3 Hz, 5′-H), 7.87 (1H, d, J=8.1 Hz, 6′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 21.43, 29.54, 30.77, 53.6, 55.83, 56.82, 78.43, 89.21, 100.25, 114.24, 116.83, 122.63, 124.54, 124.98, 127.60, 128.09, 128.35, 131.74, 132.00, 134.80, 135.66, 138.58, 139.82, 139.82, 142.72, 151.19, 151.50, 155.34. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₂H₃₄N₅O₂: 520.2750; found: 520.2751.

TBI-310, 5-(4-Methylphenyl)-3-(4-tetrahydropyranyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.64 (2H, m, —CH₂—CH₂—), 2.57 (3H, s, —CH₃), 3.42-3.91 (4H, m, —CH₂—CH₂—), 4.02 (1H, m, —CH₂—CH—CH₂—), 4.13 (3H, s, —OCH₃), 5.23 (1H, s, 4-H), 6.53 (1H, d, J=9.3 Hz, 6-H), 6.91 (1H, m, 9-H), 6.95 (1H, s, 1-H), 7.14 (2H, m, 7-H, 8-H), 7.18 (2H, d, J=8.1 Hz, 2″-H, 6″-H), 7.51 (2H, d, J=8.1 Hz, 3″-H, 5″-H), 7.71 (1H, d, J=6.0 Hz, 4′-H), 7.81 (1H, d, J=5.1 Hz, 5′-H), 7.87 (1H, d, J=8.1 Hz, 6′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 21.39, 33.29, 53.29, 53.73, 65.68, 88.97, 100.32, 114.29, 116.83, 122.83, 124.24, 124.98, 128.16, 128.36, 131.78, 131.89, 134.84, 135.26, 135.68, 138.56, 139.79, 142.62, 151.02, 151.41, 155.28. HRMS (ESI-TOF⁺): m/z [M+]⁺ calcd for C₃₀H₃₀N₅O₂: 492.2514: found: 492.2513.

TBI-311, 5-(4-Methylphenyl)-3-(2-morpholinoethyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 2.51 (3H, s, —CH₃), 2.52 (4H, m, —CH₂—CH₂—), 2.78-2.83 (4H, m, —CH₂—N—CH₂—), 3.30-3.38 (4H, m, —CH₂—O—CH₂—), 4.05 (3H, s, —OCH₃), 5.25 (1H, s, 4-H), 6.52 (1H, d, J=6.9 Hz, 6-H), 6.93 (1H, m, 6.98 (1H, s, 1-H), 7.12 (2H, m, 7-H, 8-H), 7.18 (2H, d, J=7.8 Hz, 2″-H, 6″-H), 7.30 (2H, d, J=7.8 Hz, 3″-H, 5″-H), 7.71 (1H, d, J=6.6 Hz, 4′-H), 7.82 (1H, d, J=4.5 Hz, 5′-H), 7.86 (1H, d, J=7.8 Hz, 6′-H). ¹³C NMR (100 MHz, CDCl₃) δ 21.40, 48.29, 53.71, 54.20, 59.83, 67.00, 89.09, 100.22, 114.43, 116.86, 122.90, 124.65, 127.79, 128.24, 131.99, 134.78, 135.15, 138.83, 139.83, 142.48, 153.10. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₃N₆O₂: 521.2713; found: 521.2712.

TBI-312, 5-(4-Methylphenyl)-3-cyclohexylimino-2-(2-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.17-1.74 (10H, m, —CH₂—CH₂—CH₂—CH₂—CH₂—), 2.54 (6H, s, —CH₃, py-CH₃), 3.12 (1H, m, —CH₂—CH—CH₂—), 5.30 (1H, s, 4-H), 6.53 (1H, d, J=7.5 Hz, 6-H), 6.61 (1H, s, 1-H), 7.11-7.17 (3H, m, 7-H, 8-H, 9-H), 7.20 (2H, d, J=8.1 Hz, 2″-H, 6″-H), 7.51 (2H, d, J=8.1 Hz, 3″-H, 5″-H), 7.66 (1H, d, J=6.9 Hz, 4′-H), 7.82 (1H, d, J=7.8 Hz, 5′-H), 8.24 (1H, d, J=3.6 Hz, 6′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 20.92, 21.37, 24.40, 25.91, 33.54, 57.25, 89.24, 98.81, 114.24, 121.63, 122.65, 127.42, 128.02, 128.38, 131.72, 134.92, 135.02, 135.13, 139.68, 143.80, 144.05, 150.70, 151.04, 151.89. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₂N₅: 474.2645: found: 474.2642.

TBI-313, 5-(4-Methylphenyl)-3-(N-methyl-4-piperidinyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.63 (4H, m, —CH₂—CH—CH₂—), 2.08 (2H, m, —CH₂—N—CH₂—), 2.37 (3H, s, —CH₃), 2.59 (3H, s, —N—CH₃), 2.78 (2H, m, —CH₂—N—CH₂—), 3.21 (1H, m, —CH₂—CH—CH₂—), 4.03 (3H, s, —OCH₃), 5.23 (1H, s, 4-H), 6.53 (1H, d, J=9.0 Hz, 6-H), 6.92 (1H, m, 9-H), 6.98 (1H, s, 1-H), 7.14 (2H, m, 7-H, 8-H), 7.20 (2H, J=8.4 Hz, 2″-H, 6″-H), 7.51 (2H, d, J=8.4 Hz, 3″-H, 5″-H), 7.70 (1H, d, J=6.0 Hz, 4′-H), 7.79 (1H, d, J=6.0 Hz, 5′-H), 7.86 (1H, d, J=6.0 Hz, 6′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 21.40, 32.50, 46.45, 53.36, 53.67, 89.04, 100.24, 114.26, 116.84, 122.69, 124.03, 125.07, 127.63, 128.11, 128.37, 131.79, 131.96, 134.84, 135.22, 135.67, 138.40, 139.75, 142.57, 151.21, 155.22. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₃N₆O: 505.2753; found: 505.2751.

TBI-314, 5-(4-Methylphenyl)-3-(N-isobutyl-4-piperidyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 0.92 (6H, d, J=6.6 Hz, (CH₃)₂—CH), 1.62 (4H, m, —CH₂—CH—CH₂—), 1.79 (1H, m, —CH₂—CH—CH₂—), 2.05 (4H, m, —CH₂—N—CH₂—), 2.57 (3H, s, —CH₃), 2.76 (2H, m, —N—CH₂—CH—), 3.38 (1H, m, —CH₂—CH—CH₂—), 4.02 (3H, s, —OCH₃), 5.24 (1H, s, 4-H), 6.53 (1H, d, J=7.8 Hz, 6-H), 6.91 (1H, m, 9-H), 6.97 (1H, s, 1-H), 7.14 (2H, m, 7-H, 8-H), 7.20 (2H, d, J=8.4 Hz, 2″-H, 6″-H), 7.51 (2H, d, J=8.4 Hz, 3″-H, 5″-H), 7.69 (1H, d, J=5.4 Hz, 4′-H), 7.79 (1H, d, J=4.8 Hz, 5′-H), 7.85 (1H, d, J=6.2 Hz, 6′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 21.08, 21.39, 32.68, 51.98, 53.68, 89.20, 100.20, 114.23, 122.63, 124.18, 125.06, 127.58, 128.09, 128.39, 131.77, 131.99, 134.86, 135.15, 135.66, 134.86, 135.15, 135.66, 138.43, 139.71, 142.65, 151.19. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₄H₃₉N₆O: 547.3116; found: 547.3115.

TBI-315, 5-(4-Methylphenyl)-3-(1-methylethyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.15 (6H, d, J=6.3 Hz, (CH₃)₂—CH—), 2.57 (6H, s, —CH₃, py-CH₃), 3.48 (1H, m, (CH₃)₂—CH—), 5.45 (1H, s, 4-H), 6.61 (1H, d, J=7.2 Hz, 6-H), 6.83 (1H, s, 1-H), 7.15-7.18 (3H, m, 7-H, 8-H, 9-H), 7.22 (2H, d, J=8.4 Hz, 2″-H, 6″-H), 7.53 (2H, d, J=8.4 Hz, 3″-H, 5″-H), 7.61 (1H, d, J=6.9 Hz, 4″-H), 7.78 (1H, d, J=6.9 Hz, 5″-H), 8.50 (1H, s, 2″-H). ¹³C NMR (100 MHz, CDCl₃) δ: 21.44, 22.90, 23.81, 48.83, 89.15, 99.84, 114.73, 123.29, 128.10, 128.45, 129.96, 131.86, 134.21, 134.60, 135.20, 136.31, 140.17, 144.00, 151.09, 153.50, 176.99. HRMS (ESI-TOF⁺); [M+H]⁺ calcd for C₂₈H₂₈N₅: 434.2303; found: 434.2305.

TBI-316 5-(4-Methylphenyl)-3-(4-methoxycyclohexyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.15 (2H, m, —CH₂—CH—CH₂—), 1.41 (2H, m, —CH₂—CH—CH₂—), 1.70 (2H, CH₂—CH—CH₂—), 2.08 (2H, m, —CH₂—CH—CH₂—), 2.53 (6H, s, —CH₃, py-CH₃), 3.08 (1H, m, —CH₂—CH—CH₂—), 3.18 (1H, —CH₂—CH—CH₂—), 3.38 (3H, s, —OCH₃), 5.25 (1H, s, 4-H), 6.52 (1H, d, J=8.4 Hz, 6-H), 6.74 (1H, s, 1-H), 7.09-7.14 (3H, m, 7-H, 8-H, 9-H), 7.19 (2H, d, J=7.8 Hz, 2″-H, 6″-H), 7.50 (2H, d, J=7.8 Hz: 3″-H, 5″-H), 7.67 (1H, d, J=4.5 Hz, 4-H), 7.70 (1H, d, J=4.5 Hz, 5-H), 8.43 (1H, s, 2″-H). ¹³C NMR (100 MHz, CDCl₃) δ: 21.43, 23.81, 30.00, 31.16, 55.86, 57.26, 78.63, 89.05, 98.91, 114.28, 122.69, 123.13, 127.52, 128.09, 128.31, 129.28, 131.72, 134.11, 134.81, 135.11, 125.68, 139.86, 143.68, 144.27, 150.90, 151.39, 153.22. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₂H₃₄N₅O: 504,2719: found: 504.2718.

TBI-317 5-(4-Methylphenyl)-3-(4-tetrahydropyranyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.61 (4H, m, —CH₂—CH₂—), 2.58 (6H, s, py-CH₃), 3.11-3.52 (4H, m, —CH₂—CH₂—), 3.98 (1H, m, —CH₂—CH—CH₂—), 5.23 (1H, 4-H), 6.53 (1H, d, J=7.8 Hz, 6-H), 6.77 (1H, s, 1-H), 7.11-7.18 (3H, m, 7-H, 8-H, 9-H), 7.20 (2H, d, J=7.8 Hz, 2″-H, 6″-H), 7.51 (2H, d, J=7.8 Hz, 3″-H, 5″-H), 7.67 (1H, d, J=2.7 Hz, 4″-H), 7.81 (1H, d, J=2.7 Hz, 5″-H), 8.46 (1H, s, 2″-H). ¹³C NMR (100 MHz, CDCl₃) δ: 21.36, 23.82, 33.02, 33.38, 54.31, 66.19, 88.92, 98.98, 114.32, 122.82, 123.17, 127.61, 128.16, 128.33, 129.45, 131.75, 134.02, 135.22, 135.70, 139.82, 143.75, 144.30, 150.72, 151.40, 153.39. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₃₀N₅O: 476.2527; found: 476.2526.

TBI-318 5-(4-Methylphenyl)-3-(2-morpholinoethyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 2.51 (3H, —CH₃), 2.52 (4H, m, —CH₂—CH₂—), 2.78 (2H, q, CH₂—CH₂—N—), 3.35 (2H, q, —CH₂—CH₂—N—), 2.53 (6H, s, —CH₃, py-CH₃), 5.25 (1H, s, 4-H), 6.52 (1H, d, J=8.4 Hz, 6-H), 6.74 (1H, s, 1-H), 7.09-7.14 (3H, m, 7-H, 8-H, 9-H), 7.19 (2H, d, J=7.8 Hz, 2″-H, 6″-H), 7.50 (2H, d, J=7.8 Hz, 3″-H, 5″-H), 7.67 (1H, d, J=4.5 Hz, 4″-H), 7.70 (1H, J=4.5 Hz, 5′-H), 8.43 (1H, s, 2′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 21.40, 48.29, 53.71, 54.20, 59.83, 67.00, 98.91, 114.28, 122.69, 123.13, 127.52, 128.09, 128.31, 129.28, 131.72, 134.11, 134.81, 135.11, 125.68, 139.86, 143.68, 144.27, 150.90, 151.39, 153.22. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₃N₆O: 505.2724; found: 505.2726.

TBI-319 5-(4-Methylphenyl)-3-(N-methyl-4-piperidyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.65 (4H, m, —CH₂—CH₂—), 2.01 (2H, m, —CH₂—N—CH₂—), 2.27 (3H, s, —NCH₃), 2.55 (6H, s, —CH₃, -py-CH₃), 2.77 (2H, m, —CH₂—N—CH₂—), 3.13 (1H, m, —CH₂—CH—CH₂—), 5.27 (1H, s, 4-H), 6.53 (1H, d, J=7.5 Hz, 6-H), 6.75 (1H, s, 1-H), 7.10-7.17 (3H, m, 7-H, 8-H, 9-H), 7.19 (2H, d, J=8.1 Hz, 2″-H, 6″-H), 7.52 (2H, d, J=8.1 Hz, 3″-H, 5″-H), 7.68 (1H, d, J=2.7 Hz, 4′-H), 7.61 (1H, d, J=2.7 Hz, 5′-H), 8.45 (1H, d, 2′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 21.38, 23.82, 32.61, 64.39, 54.00, 89.08, 98.92, 114.31, 122.75, 123.17, 127.54, 128.33, 129.40, 131.75, 134.10, 134.87, 135.17, 135.71, 139.77, 143.76, 144.29, 151.35, 153.33. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₃N₆: 489.2776: found: 489.2775.

TBI-320 5-(4-Methylphenyl)-3-(N-isobutyl-4-piperidyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 0.89 (6H, d, J=6.61 Hz, (CH₃)₂—CH), 1.61-2.08 (9H, m, —CH₂—CH₂—CH—CH₂—CH₂), 2.55 (6H, s, —CH₃, -py-CH₃, 2.77 (2H, m, —N—CH₂—CH), 3.10 (1H, m, —CH—(CH₃)₂), 5.23 (1H, s, 4-H), 6.74 (1H, d, J=7.5 Hz, 6-H), 6.75 (1H, s, 1-H), 7.09-7.18 (3H, m, 7-H, 8-H, 9-H), 7.20 (2H, d, J=7.8 Hz, 2″-H, 6″-H), 7.51 (2H, d, J=7.8 Hz, 3-H, 5″-H), 7.67 (1H, d, J=7.8 Hz, 4′-H), 7.61 (1H, d, J=7.8 Hz, 5′-H), 8.45 (1H, s, 2′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 20.97, 21.38, 23.82, 25.73, 32.77, 52.48, 55.86, 67.11, 89.15, 98.83, 114.24, 122.67, 123.14, 127.45, 128.09, 128.37, 129.22, 131.73, 134.18, 134.91, 135.12, 135.69, 139.69, 143.66, 144.31, 151.13, 153.17. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₄H₃₉N₅: 531.3403: found: 531.3400.

TBI-321, 5-(4-Methylphenyl)-3-(1-methylethyl)imino-2-(2-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.13 (6H, d, J=5.7 Hz, (CH₃)₂—CH—), 2.53 (6H, s, —CH₃, py-CH₃), 3.47 (1H, m, —CH—(CH₃)₂), 5.41 (1H, 4-H), 6.53 (1H, s, 6-H), 6.59 (1H, s, 1-H), 7.15-7.18 (3H, m, 7-H, 8-H, 9-H), 7.20 (2H, d, J=8.1 Hz, 2″-H, 6″-H), 7.52 (2H, d, J=8.1 Hz, 3″-H, 5″-H), 7.71 (1H, d, J=6.6 Hz, 4′-H), 7.81 (1H, d, J=8.1 Hz, 5′-H), 8.30 (1H, d, J=4.2 Hz, 6′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 20.94, 21.44, 23.14, 48.87, 89.07, 99.42, 114.57, 121.74, 123.19, 128.20, 129.70, 131.85, 134.71, 135.21, 136.02, 141.02, 144.07, 144.36, 150.83. HRMS (ESI-TOF⁺); m/z [M+H]⁺ calcd for C₂₈H₂₈N₅: 434.2330; found: 434.2334.

TBI-322, 5-(4-Methylphenyl)-3-(4-methoxycyclohexyl)imino-2-(2-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.21 (2H, m, —CH₂—CH₂—), 1.41 (2H, m, —CH₂—CH₂), 1.17 (2H, m, 2.05 (2H, m, —CH₂—CH₂—CH₂—), 2.52 (6H, s, —CH₃, py-CH₃), 3.10 (1H, m, —CH₂—CH—CH₂—), 3.35 (1H, m, —CH₂—CH₂—CH₂—), 3.75 (3H, s, —OCH₃), 5.25 (1H, s, 4-H), 6.52 (1H, d, J=8.4 Hz, 6-H), 6.61 (1H, s, 1-H), 7.08-7.15 (3H, m, 7-H, 8-H, 9-H), 7.18 (2H, d, J=7.8 Hz, 2″-H, 6″-H), 7.50 (2H, d, J=7.8 Hz, 3′-H, 5″-H), 7.68 (1H, d, J=7.5 Hz, 4′-H), 7.72 (1H, d, J=7.2 Hz, 5′-H), 8.27 (1H, d, J=3.6 Hz, 6′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 20.91, 21.44, 29.73, 30.99, 55.85, 56.88, 78.45, 89.01, 98.96, 114.32, 121.65, 122.73, 127.57, 128.09, 128.30, 128.81, 131.75, 134.82, 135.17, 135.66, 139.89, 143.97, 150.90, 151.32, 151.97. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃H₃₄N₅O: 504.2765; found: 504.2767.

TBI-323 5-(4-Methylphenyl)-3-(4-tetrahydropyranyl)imino-2-(2-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.67 (4H, m, —CH₂—CH₂—), 2.52 (6H, s, —CH₃, py-CH₃), 3.32-3.51 (3H, m, —CH₂—CH—CH₂—), 3.92-4.01 (2H, m, 5.23 (1H, s, 4-H), 6.44 (1H, d, J=8.7 Hz, 6-H), 6.63 (1H, s, 1-H), 7.10-7.18 (3H, m, 7-H, 8-H, 9-H), 7.20 (2H, d, J=8.1 Hz, 2″-H, 6″-H), 7.32 (2H, d, J=8.1 Hz, 3″-H, 5″-H), 7.68 (1H, d, J=7.5 Hz, 4′-H), 7.72 (1H, d, J=7.8 Hz, 5′-H), 8.28 (1H, d, J=3.9 Hz, 6′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 20.95, 21.38, 33.03, 33.34, 53.65, 65.91, 88.86, 99.03, 114.36, 121.67, 122.86, 127.67, 128.16, 128.32, 128.82, 131.79, 134.72, 134.85, 135.67, 139.86, 143.92, 144.07, 150.73, 151.32, 151.98. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₃₀N₅O: 476.2453; found: 476.2450.

TBI-324 5-(4-Methylphenyl)-3-(2-morpholinoethyl)imino-2-(2-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 2.48 (4H, m, —CH₂—O—CH₂), 2.57 (6H, s, —CH₃, py-CH₃), 2.73 (2H, m, —CH₂—CH₂—), 3.36 (2H, m, —CH₂—CH₂—), 3.70 (4H, m, (1H, s, 4-H), 6.57 (1H, s, 6-H), 6.62 (1H, s, 1-H), 7.10-7.15 (3H, m, 7-H, 8-H, 9-H), 7.18 (2H, d, J=6.9 Hz, 2″-H, 6″-H), 7.51 (2H, d, J=6.9 Hz, 3″-H, 5″-H), 7.71 (1H, s, 4′-H), 7.81 (1H, d, J=7.8 Hz, 5′-H), 8.30 (1H, s, 6′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 20.98, 21.41, 47.96, 54.15, 60.02, 66.95, 88.95, 98.98, 114.48, 121.72, 122.97, 127.71, 128.22, 129.24, 132.02, 134.82, 135.23, 135.72, 139.88, 143.89, 144.28, 152.92. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₃N₆O: 505.2847; found: 505.2846.

TBI-325 5-(4-Methylphenyl)-3-(N-isobutyl-4-piperidyl)imino-2-(2-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 0.79 (6H, d, J=6.2 Hz, (CH₃)₂—CH—), 1.62 (4H, m, —CH₂—CH—CH₂—), 1.75 (1H, m, CH₂—CH—CH₂—), 1.92-2.09 (4H, m, —CH₂—N—CH₂—), 2.57 (6H, s, —CH₃, py-CH₃), 2.71 (2H, q, —CH₂—CH—), 3.15 (1H, m, (CH₃)₂—CH—), 5.25 (1H, s, 4-H), 6.54 (1H, d, J=7.8 Hz, 6-H), 6.65 (1H, s, 1-H), 7.08-7.18 (3H, m, 7-H, 8-H, 9-H), 7.21 (2H, d, J=8.1 Hz, 2″-H, 6″-H), 7.51 (2H, d, J=8.1 Hz, 3″-H, 5″-H), 7.68 (1H, d, J=8.4 Hz, 4′-H), 7.86 (1H, d, J=7.8 Hz, 5′-H), 8.25 (1H, d, J=3.6 Hz, 6′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 21.01, 21.38, 25.69, 32.76, 52.20, 55.15, 67.25, 89.08, 98.89, 114.28, 121.63, 122.71, 127.51, 128.08, 128.36, 131.76, 134.89, 135.19, 135.66, 139.74, 143.79, 151.04, 151.77. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₄H₃₉N₆: 531.3357: found: 531.3359.

TBI-326 5-(4-Methylphenyl ethyl-4-piperidyl)imino-2-(2-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.60-1.78 (4H, m, —CH₂—CH₂—), 2.05-2.15 (2H, m, —CH₂—CH₂—), 2.29 (3H, s, —N—CH₃), 2.53 (6H, s, py-CH₃), 2.70-2.80 (2H, m, —CH₂—CH₂—), 3.19 (1H, m, —CH₂—CH—CH₂—), 5.28 (1H, s, 4-H), 6.52 (1H, d, J=7.2 Hz, 6-H), 6.68 (1H, s, 1-H), 7.09-7.15 (3H, m, 7-H, 8-H, 9-H), 7.20 (2H, d, J=8.4 Hz, 2″-H, 6″H), 7.52 (2H, d, J=8.4 Hz, 3″-H, 5″-H), 7.70 (1H, d, J=6.9 Hz, 4′-H), 7.85 (1H, d, J=8.1 Hz, 5′-H), 8.28 (1H, d, J=3.9 Hz, 6′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 20.98, 21.40, 32.43, 46.36, 53.54, 88.98, 98.96, 114.38, 121.68, 122.88, 127.67, 128.28, 131.80, 134.81, 135.26 139.86, 143.77, 151.20. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₃N₆: 489.2862: found: 489.2860.

TBI-327, 5-(4-Methylphenyl)-3-(1-methylethyl)imino-2-(5-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.09 (6H, d, J=6.0 Hz, (CH₃)₂—CH—), 2.37 (3H, s, —CH₃), 2.52 (3H, s, py-CH₃), 3.34 (1H, m, (CH₃)₂—CH—), 5.33 (1H, s, 4-H), 6.51 (1H, d, J=8.4 Hz, 6-H), 6.83 (1H, s, 1-H), 7.08-7.17 (2H, m, 7-H, 8-H), 7.20 (2H, d, J=7.5 Hz, 2″-H, 6″-H), 7.49 (2H, d, J=7.5 Hz, 3″-H, 5″-H), 7.59 (1H, s, 4″-H), 7.69 (1H, d, J=7.5 Hz, 9-H), 8.18 (1H, s, 6″-H), 8.39 (1H, s, 2″-H). ¹³C NMR (100 MHz, CDCl₃) δ: 18.46, 21.43, 23.52, 49.23, 89.04, 99.33, 114.26, 122.68, 127.53, 128.05, 128.26, 128.40, 131.82, 133.44, 134.88, 135.15, 135.65, 136.60, 139.72, 141.08, 143.75, 144.78, 150.61, 151.04. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₈N₅: 434.2331; found: 434.2330.

TBI-328, 5-(4-Methylphenyl)-3-(4-tetrahydropyranyl)imino-2-(5-ethyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.57-1.67 (4H, m, —CH₂—CH—CH₂—), 2.38 (3H, s, —CH₃), 2.53 (3H, s, py-CH₃), 3.32-3.43 (3H, m, —CH₂—CH—CH₂—), 3.93-4.02 (2H, m, —CH—CH₂—CH₂—), 5.24 (1H, s, 4-H), 6.58 (1H, d, J=7.5 Hz, 6-H), 6.87 (1H, s, 1-H), 7.11-7.18 (2H, m, 7-H, 8-H), 7.21 (2H, d, J=7.5 Hz, 2″-H, 6″-H), 7.42 (2H, d, J=7.5 Hz, 3″-H, 5″-H), 7.58 (1H, s, 4-H), 7.72 (1H, d 7.5 Hz, 9-H), 8.18 (1H, s, 6″-H), 8.41 (1H, s, 2″-H). ¹³C NMR (100 MHz, CDCl₃) δ: 18.44, 21.37, 33.36, 54.24, 66.16, 88.94, 99.49, 114.35, 122.87, 127.76, 128.18, 128.32, 131.77, 133.53, 134.82, 135.25, 135.67, 136.38, 139.86, 141.06, 143.3, 144.95, 150.77, 151.35. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₃₀N₅O: 476.2450; found: 476.2453.

TBI-329, 5-(4-Methylphenyl)-3-cyclohexylimino-2-(5-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.38-1.78 (10H, m, —CH₂—CH₂—CH₂—CH₂—CH₂—), 2.38 (3H, s, —CH₃), 2.53 (3H, s, py-CH₃), 3.06 (1H, m, —CH₂—CH—CH₂—), 5.28 (1H, s, 4-H), 6.54 (1H, d, J=8.1 Hz, 6-H), 6.83 (1H, s, 1-H), 7.08-7.18 (2H, m, 7-H, 8-H), 7.20 (2H, d, J=7.2 Hz, 2-H, 6″-H), 7.31 (2H, d, J=7.2 Hz, 3″-H, 5″-H), 7.59 (1H, s, 4′-H), 7.69 (1H, d, J=7.5 Hz, 9-H), 8.15 (1H, s, 6′-H), 8.38 (1H, s, ¹³C NMR (100 MHz, CDCl₃) δ: 18.46, 21.37, 24.64, 25.87, 33.57, 57.74, 89.34, 99.29, 114.23, 122.65, 127.51, 128.04, 128.19, 128.39, 131.71, 133.45, 134.90, 135.09, 135.68, 136.65, 139.68, 141.03, 143.77, 144.71, 150.75, 151.09. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₂N₅: 474.2811; found: 474.2810.

TBI-330, 5-(4-Methylphenyl)-3-(4-methoxycyclohexyl)imino-2-(5-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.10-1.46 (4H, m, —CH₂—CH—CH₂—), 1.68 (2H, m, —CH₂—CH₂—), 2.08 (2H, m, —CH₂—CH₂—), 2.38 (3H, s, —CH₃), 2.54 (3H, s, py-CH3), 3.05 (1H, m, —CH₂—CH₂—CH₂—), 3.18 (1H, m, —CH₂—CH—CH₂—), 3.36 (3H, s, —OCH3), 5.29 (1H, s, 4-H), 6.53 (1H, d, J=7.8 Hz, 6-H), 6.85 (1H, s, 1-H), 7.11-7.15 (2H, m, 7-H, 8-H), 7.19 (2H, d, J=8.1 Hz, 2″-H, 6″-H), 7.50 (2H, d, J=8.1 Hz, 3″-H, 5″-H), 7.59 (1H, s, 4′-H), 7.69 (1H, d, J=7.5 Hz, 9-H), 8.18 (1H, s, 6′-H), 8.28 (1H, s, 2′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 18.46, 21.44, 29.95, 31.11, 55.86, 57.20, 78.59, 89.08, 99.43, 114.32, 122.74, 127.67, 128.10, 128.29, 131.75, 133.48, 135.15, 135.65, 136.48, 139.90, 141.03, 143.62, 144.81, 150.93, 151.34. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₂H₃₄N₅O: 504.2765; found: 504.2767.

TBI-331, 5-(4-Methylphenyl)-3-cyclohexylimino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.18-1.78 (10H, m, —CH₂—CH₂—CH₂—CH₂—CH₂—), 2.54 (3H, s, —CH₃), 3.12 (1H, m, —CH₂—CH—CH₂—), 4.03 (3H, s, —OCH₃), 5.28 (1H, s, 4-H), 6.52 (1H, d, J=8.4 Hz, 6-H), 6.90 (1H, m, 9-H), 6.94 (1H, s, 1-H), 7.08-7.15 (2H, m, 7-H, 8-H), 7.20 (2H, d, J=7.8 Hz, 2″-H, 6″-H), 7.48 (2H, d, J=7.8 Hz, 3″-H, 5″-H), 7.68 (1H, d, J=4.5 Hz, 4′-H), 7.78 (1H, d, J=4.5 Hz, 5′-H), 7.85 (1H, d, J=7.5 Hz, 6′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 21.36, 24.26, 26.01, 33.47, 53.67, 89.45, 100.14, 114.15, 116.81, 122.52, 124.42, 125.09, 127.48, 128.02, 128.44, 131.71, 132.05, 134.92, 135.02, 135.64, 138.47, 139.60, 142.83, 150.84, 151.36, 155.35. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₂N₅O: 490.4489; found: 490.4486.

TBI-332, 5-(4-Methylphenyl)-3-(4-hydroxycyclohexyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.14-1.31 (4H, m, —CH₂—CH—CH₂—), 1.45-1.73 (4H, m, —CH₂—CH—CH₂—), 2.55 (3H, s, —CH₃), 3.10 (1H, m, —CH₂—CH—CH₂—), 3.72 (1H, m, —CH₂—CH—CH₂—), 4.04 (3H, s, —OCH₃), 5.27 (1H, s, 4-H), 6.55 (1H, d, J=6.9 Hz, 6-H), 6.95 (1H, m, 9-H), 6.94 (1H, s, 1-H), 7.03-7.15 (2H, m, 7-H, 8-H), 7.20 (2H, d, J=7.8 Hz, 2″-H, 6″-H), 7.48 (2H, d, J=7.8 Hz, 3″-H, 5″-H), 7.70 (1H, d, J=6.9 Hz, 4′-H), 7.80 (1H, d, J=4.2 Hz, 5′-H), 7.85 (1H, d, J=2.7 Hz, 6′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 21.43, 30.85, 33.33, 53.59, 56.69, 69.88, 89.21, 100.22, 114.26, 122.66, 124.62, 124.94, 127.63, 128.10, 128.35, 131.75, 134.81, 135.10, 135.66, 136.53, 138.62, 139.81, 142.72, 151.60. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₂N₅O₂: 506.2957; found: 506.2958.

TBI-333, 5-(4-Methylphenyl)-3-cyclohexylimino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.10-1.60 (10H, m, —CH₂—CH₂—CH₂—CH₂—CH₂—), 2.54 (3H, s, —CH₃), 3.07 (1H, m, —CH₂—CH—CH₂—), 5.29 (1H, s, 4-H), 6.53 (1H, d, J=8.1 Hz, 6-H), 6.91 (1H, s, 1-H), 7.10-7.14 (2H, m, 7-H, 8-H), 7.18 (2H, d, J=8.4 Hz, 2″-H, 6″-H), 7.30 (1H, m, 9-H), 7.51 (2H, d, J=8.4 Hz, 3″-H, 5″-H), 7.68 (1H, d, J=4.8 Hz, 4′-H), 7.79 (1H, d, J=7.8 Hz, 5′-H), 8.32 (1H, d, J=4.8 Hz, 6′-H), 8.57 (1H, d, J=2.4 Hz, 2′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 21.37, 24.64, 25.87, 33.57, 57.74, 89.32, 99.37, 114.25, 122.68, 123.60, 127.57, 127.72, 128.13, 128.38, 131.72, 131.89, 134.89, 135.12, 135.71, 137.09, 143.69, 143.86, 144.05, 150.77, 151.00. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₃₀N₅: 460.2753; found: 460.2752.

TBI-334, 5-(4-Methylphenyl)-3-(4-hydroxycyclohexyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.17-1.51 (4H, m, —CH₂—CH—CH₂—), 1.67-2.04 (4H, m, —CH₂—CH—CH₂—), 2.54 (6H, s, —CH₃, -py-CH₃), 3.06 (1H, m, —CH₂—CH—CH₂—), 3.56 (1H, m, —CH₂—CH—CH₂—), 5.28 (1H, s, 4-H), 6.53 (1H, d, J=8.7 Hz, 6-H), 6.73 (1H, s, 1-H), 7.10-7.18 (3H, m, 7-H, 8-H, 9-H), 7.23 (2H, d, J=8.1 Hz, 2″-H, 6″-H), 7.50 (2H, d, J=8.1 Hz, 3″-H, 5″-H), 7.67 (1H, d, J=8.1 Hz, 4-H), 7.61 (1H, d, J=8.1 Hz, 5′-H), 8.45 (1H, s, 2′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 21.43, 23.78, 31.21, 33.69, 57.05, 70.04, 89.03, 98.90, 114.29, 122.29, 123.17, 127.54, 128.09, 128.33, 129.31, 131.74, 134.13, 135.12, 135.67, 139.83, 143.65, 144.27, 150.89, 151.46, 153.23. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₂N₅O: 490.2673: found: 490.2672.

TBI-335, 5-(4-Methylphenyl)-3-(4-hydroxycyclohexyl)imino-2-ethyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.13-1.46 (4H, m, —CH₂—CH₂—), 1.49-2.04 (4H, m, —CH₂—CH₂—), 2.54 (6H, s, —CH₃, py-CH₃), 3.71 (1H, m, —CH₂—CH—CH₂—), 4.21 (1H, m, —CH₂—CH—CH₂—), 5.30 (1H, s, 4-H), 6.53 (1H, d, 7.8 Hz, 6-H), 6.61 (1H, s, 1-H), 7.11-7.17 (3H, m, 7-H, 8-H, 9-H), 7.24 (2H, d, J=8.1 Hz, 2″-H, 6″-H), 7.50 (2H, d, 8.1 Hz, 3″-H, 5″-H), 7.68 (1H, d, J=7.2 Hz, 4′-H), 7.82 (1H, d, J=7.8 Hz, 5′-H), 8.26 (1H, d, J=4.2 Hz, 6′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 20.90, 21.43, 31.05, 33.47, 56.70, 69.84, 89.01, 98.99, 114.35, 121.69, 122.79, 127.62, 127.62, 128.11, 128.93, 131.77, 134.80, 135.18, 139.90, 143.99, 151.39. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₂N₅O: 490.2842; found: 490.2845.

TBI-336, 5-(3,4-Dichlorophenyl)-3-(1-methylethyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.13 (6H, d, J=7.9 Hz, —CH—(CH₃)₂), 3.50 (1H, m, —CH—(CH₃)₂), 5.30 (1H, s, 4-H), 6.45 (1H, d, J=7.5 Hz, 6-H), 6.82 (1H, s, 1-H), 7.17-7.24 (2H, 7-H, 8-H), 7.29-7.32 (2H, m, 5″-H, 6″-H), 7.51 (1H, s, 2″-H), 7.70 (1H, d, J=7.5 Hz, 4′-H), 7.72 (1H, d, J=7.8 Hz, 5′-H), 7.82 (1H, d, J=7.8 Hz, 9-H), 8.34 (1H, d, J=4.5 Hz, 6′-H), 8.59 (1H, s, 2′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 23.61, 49.49, 89.18, 99.46, 113,66, 123.23, 123.64, 127.83, 128.03, 128.44, 128.56, 131.21, 133.12, 134.38, 134.58, 135.52, 136.76, 143.69, 144.01, 144.37, 150.16, 150.94. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₆H₂₂Cl₂N₅: 475.1295; found: 475.1296.

TBI-337, 5-(4-Methylphenyl)-3-(4-hydroxycyclohexyl)imino-2-(5-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.17-1.50 (4H, m, —CH₂—CH—CH₂—), 1.66-1.70 (2H, m, —CH₂—CH—CH₂—), 1.95-2.04 (2H, m, —CH₂—CH—CH₂—), 2.27 (3H, s, —CH₃), 2.54 (3H, s, py-CH₃), 3.06 (1H, m, —CH₂—CH—CH₂—), 3.70 (1H, m, —CH₂—CH—CH₂—), 5.29 (1H, s, 4-H), 6.53 (1H, d, J=7.5 Hz, 6-H), 6.84 (1H, s, 1-H), 7.13-7.18 (2H, m, 7-H, 8-H), 7.19 (2H, d, J=7.8 Hz, 2″-H, 6″-H), 7.51 (2H, d, J=7.8 Hz, 3″-H, 5″-H), 7.58 (1H, s, 4′-H), 7.70 (1H, d, J=7.8 Hz, 9-H), 8.16 (1H, s, 6′-H), 8.38 (1H, s, 2′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 18.45, 21.44, 31.18, 33.65, 57.01, 70.02, 89.07, 99.43, 114.32, 122.77, 127.68, 128.31, 131.77, 133.51, 134.80, 135.16, 135.66, 136.47, 139.87, 141.02, 143.61, 144.82, 150.93, 151.41. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₂N₅O: 490.2843; found: 490.2845.

TBI-338, 5-(4-Methylphenyl)-3-(4-hydroxycyclohexyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.21-1.50 (4H, m, —CH₂—CH—CH₂—), 1.67-1.99 (4H, m, —CH₂—CH—CH₂—), 2.54 (3H, s, —CH₃), 3.06 (1H, m, —CH₂—CH—CH₂—), 3.69 (1H, m, —CH₂—CH—CH₂—), 5.29 (1H, s, 4-H), 6.53 (1H, d, J=7.5 Hz, 6-H), 6.85 (1H, s, 1-H), 7.15-7.25 (2H, m, 7-H, 8-H), 7.27 (2H, d, J=6.9 Hz, 2″-H, 6″-H), 7.32 (1H, m, 9-H), 7.51 (2H, d, J=6.9 Hz, 3″-H, 5″-H), 7.69 (1H, d, J=7.2 Hz, 4′-H), 7.78 (1H, d, J=7.8 Hz, 5′-H), 8.31 (1H, s, 6′-H), 8.57 (1H, s, 2′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 21.43, 33.65, 57.00, 69.98, 89.06, 99.54, 114.33, 122,80, 123.64, 127.77, 128.28, 131.76, 134.75, 135.17, 135.66, 136.86, 139.89, 143.48, 143.82, 144.12, 150.80, 151.40. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₃₀N₅O: 476.2871; found: 476.2870.

TBI-339, 5-(4-Methylphenyl)-3-cyclopropylimino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 0.80-0.86 (4H, —CH₂—CH₂—), 2.55 (3H, s, —CH), 2.73 (1H, m, —CH₂—CH—CH₂—), 4.01 (3H, s, —OCH₃), 5.59 (1H, s, 4-H), 6.46 (1H, d, J=7.8 Hz, 6-H), 6.94 (1H, m, 9-H), 7.12 (1H, s, 1-H), 7.16-7.21 (2H, m, 7-H, 8-H), 7.20 (2H, d, J=7.5 Hz, 2″-H, 6″-H), 7.49 (2H, d, J=7.5 Hz, 3″-H, 5″-H), 7.67 (1H, d, J=7.2 Hz, 4′-H), 7.80 (1H, d, J=7.2 Hz, 5′-H), 7.85 (1H, d, J=7.2 Hz, 6′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 9.91, 21.42, 32.77, 53.67, 89.26, 100.11, 114.16, 116.81, 122.55, 124.93, 127.50, 127.97, 128.52, 131.86, 132.23, 134.91, 135.75, 138.69, 139.60, 142.62, 151.49, 152.90, 155.40. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₆N₅O: 448.3371; found: 448.3370.

TBI-340, 5-(4-Methylphenyl)-3-cyclopropylimino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 0.79-0.86 (4H, —CH₂—CH₂—), 2.54 (6H, s, —CH₃, -py-CH₃), 3.73 (1H, m, —CH₂—CH—CH₂—), 5.60 (1H, s, 4-H), 6.47 (1H, d, J=7.5 Hz, 6-H), 6.69 (1H, s, 1-H), 7.07-7.16 (3H, m, 7-H, 8-H, 9-H), 7.22 (2H, d, J=7.8 Hz, 2″-H, 6″-H), 7.50 (2H, d, J=7.8 Hz, 3″-H, 5″-H), 7.65 (1H, d, J=5.1 Hz, 4′-H), 7.67 (1H, d, J=5.1 Hz, 5′-H), 8.41 (1H, s, 2′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 9.76, 21.42, 23.81, 32.72, 89.40, 98.86, 114.22, 122.63, 123.16, 127.6, 128.01, 128.48, 129.53, 131.86, 132.05, 134.00, 134.95, 135.77, 139.65, 143.80, 144.14, 151.22. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₆N₅: 432.2232; found: 432.2235.

TBI-341, 5-(4-Methylphenyl)-3-cyclopropylimino-2-(2-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 0.78-0.89 (4H, m, —CH₂—CH₂—), 2.54 (6H, s, —CH₃, py-CH₃), 2.77 (1H, m, —CH₂—CH—CH₂—), 5.61 (1H, s, 4-H), 6.48 (1H, d, J=7.8 Hz, 6-H), 6.53 (1H, s, 1-H), 7.11-7.19 (3H, m, 7-H, 8-H, 9-H), 7.25 (2H, d, J=8.1 Hz, 2″-H, 6″-H), 7.51 (2H, J=8.1 Hz, 3″-H, 5″-H), 7.66 (1H, d, J=7.2 Hz, 4″-H), 7.79 (1H, d, J=8.1 Hz, 5′-H), 8.29 (1H, d, J=4.2 Hz, 6′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 9.97, 20.90, 21.43, 32.69, 89.32, 98.89, 114.21, 121.67, 122.62, 127.46, 127.97, 128.48, 129.55, 131.87, 132.08, 134.63, 134.98, 135.72, 139.65, 143.98, 144.30, 151.23, 152.41. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₆N₅: 432.2641; found: 432.2639.

TBI-342, 5-(4-Methylphenyl)-3-cyclopropylimino-2-(5-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 0.78-0.86 (4H, m, —CH₂—CH₂—), 2.27 (3H, s, —CH₃), 2.53 (3H, s, py-CH₃), 2.72 (1H, m, —CH₂—CH—CH₂—), 5.59 (1H, s, 4-H), 6.47 (1H, d, J=72 Hz, 6-H), 6.79 (1H, s, 1-H), 7.10-7.17 (2H, m, 7-H, 8-H), 7.22 (2H, d, J=7.5 Hz, 2″-H, 6″-H), 7.49 (2H, d, J=7.5 Hz, 3″-H, 5″-H), 7.56 (1H, s, 4′-H), 7.67 (1H, d, J=7.8 Hz, 9-H), 8.16 (1H, s, 6′-H), 8.35 (1H, s, 2′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 9.82, 18.45, 21.43, 32.74, 89.42, 99.34, 114.23, 122, 65, 127.58, 129.01, 128.47, 131.88, 133.48, 134.97, 135.74, 136.34, 139.67, 141.15, 143.48, 144.92, 151.27, 152.68. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₆N₅: 432.2639; found: 432.2637.

TBI-343, 5-(3,4-Dichlorophenyl)-3-cyclopropylimino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 0.85-0.96 (4H, m, —CH₂—CH₂—), 2.77 (1H, m, —CH₂—CH—CH₂—), 5.55 (1H, s, 4-H), 6.42 (1H, d, J=7.5 Hz, 6-H), 6.76 (1H, s, 1-H), 7.13-7.20 (2H, m, 7-H, 8-H), 7.28-7.31 (2H, m, 5″-H, 6″-H), 7.51 (1H, s, 2″-H), 7.65 (1H, d, J=7.8 Hz, 4′-H), 7.75 (1H, d, J=7.8 Hz, 5′-H), 7.81 (1H, d, J=8.4 Hz, 9-H), 8.33 (1H, d, J=4.5 Hz, 6′-H), 8.54 (1H, s, 2′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 10.23, 33.10, 89.59, 99.42, 113.63, 123.19, 123.65, 127.82, 128.21, 128.37, 128.70, 131.33, 133.19, 134.39, 135.39, 135.63, 136.56, 136.77, 143.48, 144.10, 144.50, 151.76, 152.01. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₆H₂₀Cl₂N₅: 473.1143: found: 473.1147.

TBI-344, 5-(4-Methylphenyl)-3-cyclobutylimino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.65-1.80 (2H, m, —CH₂—CH₂—CH₂—), 2.01-2.22 (4H, m, —CH₂CH₂—CH₂—), 2.55 (3H, s, —CH₃), 3.85 (1H, m, —CH₂—CH—CH₂—), 4.04 (3H, s, —OCH₃), 5.15 (1H, s, 4-H), 6.54 (1H, J=7.5 Hz, 6-H), 6.91 (1H, m, 9-H), 6.93 (1H, s, 1-H), 7.14-7.16 (2H, m, 7-H, 8-H), 7.20 (2H, d, J=8.1 Hz, 2″-H, 6″-H), 7.51 (2H, d, J=8.1 Hz, 3″-H, 5″-H), 7.72 (1H, d, J=7.2 Hz, 4′-H), 7.82 (1H, d, J=7.2 Hz, 5′-H), 7.85 (1H, s, 6′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 16.01, 21.43, 31.78, 53.70, 54.57, 90.69, 100.52, 114.40, 116.84, 122.93, 124.76, 125.26, 127.77, 128.19, 128.38, 131.76, 134.69, 134.77, 135.87, 138.99, 139.82, 142.70, 150.91, 151.68, 155.57. HRMS (ESI-TOF⁺): m/z. [M+H]⁺ calcd for C₂₉H₂₈N₅O: 462.4060; found: 462.4058.

TBI-345, 5-(4-Methylphenyl)-3-cyclobutylimino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.65-2.12 (6H, m, —CH₂—CH₂—CH₂—), 2.56 (3H, s, —CH₃), 3.87 (1H, m, —CH₂—CH—CH₂—), 5.17 (1H, s, 4-H), 6.55 (1H, d, 17.2 Hz, 6-H), 6.88 (1H, s, 1-H), 7.11-7.18 (2H, m, 7-H, 8-H), 7.21 (2H, d, J=8.1 Hz, 2″-H, 6″-H), 7.31 (1H, m, 9-H), 7.52 (2H, d, J=8.1 Hz, 3″-H, 5″-H), 7.71 (1H, d, J=6.9 Hz, 4′-H), 7.79 (1H, d, J=7.8 Hz, 5′-H), 8.32 (1H, d, J=6.9 Hz, 6′-H), 8.61 (1H, s, 2′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 16.01, 21.34, 31, 72, 54.51, 90.52, 99.76, 114.50, 123.07, 123.67, 127.96, 128.31, 131.79, 134.79, 135.89, 136.83, 139.93, 143.98, 144.30, 151.43. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₆N₅: 432.2232: found: 432.2235.

TBI-346, 5-(4-Methylphenyl)-3-cyclobutylimino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.65-1.79 (2H, m, —CH₂—CH₂—CH₂—), 2.00-2.18 (4H, m, —CH₂—CH₂—CH₂—), 2.56 (6H, s, —CH₃, -py-CH₃), 3.86 (1H, m, —CH₂—CH—CH₂), 5.14 (1H, s, 4-H), 6.53 (1H, d, J=6.9 Hz, 6-H), 6.70 (1H, s, 1-H), 7.14-7.17 (3H, m, 7-H, 8-H, 9-H), 7.20 (2H, d, J=7.8 Hz, 2″-H, 6″-H), 7.51 (2H, d, J=7.8 Hz, 3″-H, 5″-H), 7.65 (1H, s, 4′-H), 7.79 (1H, d, s, 5′-H), 8.47 (1H, s, 2′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 16.01, 21.42, 23.81, 31.889, 54.73, 90.51, 98.94, 114.36, 122.82, 123.188, 127.58, 128.13, 129.45, 131.75, 134.50, 134.71, 135.75, 139.76, 143.75, 144.24, 150.84, 151.46. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₈N₅: 446.2436: found: 446.2435.

TBI-347, 5-(4-Methylphenyl)-3-cyclobutylimino-2-(2-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.68-1.81 (2H, m, —CH₂—CH₂—CH₂—), 2.04-2.22 (4H, m, —CH₂—CH₂—CH₂—), 2.56 (6H, s, —CH₃, py-CH₃), 3.89 (1H, m, —CH₂—CH—CH₂—), 5.22 (1H, s, 4-H), 6.55 (1H, s, 1-H), 6.50 (1H, d, J=7.8 Hz, 6-H), 7.16-7.20 (3H, m, 7-H, 8-H, 9-H), 7.22 (2H, d, J=8.1 Hz, 2″-H, 6″-H), 7.53 (2H, d, J=8.1 Hz, 3″-H, 5″-H), 7.73 (1H, d, J=7.8 Hz, 4′-H), 7.88 (1H, d, J=7.8 Hz, 5′-H), 8.30 (1H, d, J=69 Hz, 6′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 16.01, 20.99, 21.43, 24.03, 31.44, 53.98, 90.45, 99.57, 114.68, 121.77, 123.43, 128.00, 128.21, 128.43, 130.29, 131.79, 134.65, 134.79, 136.14, 137.36, 140.08, 143.97, 144.72, 150.15, 151.41, 152.96. HRMS (ESI-TOF⁺): m/z [M+H]⁺ called for C₂₉H₂₈N₅: 446.2588; found: 446.2587.

TBI-348, 5-(4-Methylphenyl)-3-cyclobutylimino-2-(5-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.64-1.80 (2H, m, —CH₂—CH₂—CH₂—), 2.04-2.18 (4H, m, —CH₂—CH₂—CH₂—), 2.37 (3H, s, —CH₃), 2.56 (3H, s, py-CH₃), 3.87 (1H, m, —CH₂—CH—CH₂—), 5.22 (1H, s, 4-H), 6.62 (1H, d, J=8.1 Hz, 6-H), 6.93 (1H, s, 1-H), 7.16-7.19 (2H, m, 7-H, 8-H), 7.22 (2H, d, 8.1 Hz, 2″-H, 6″-H), 7.52 (2H, d, J=8.1 Hz, 3″-H, 5″-H), 7.60 (1H, s, 4′-H), 7.77 (1H, d, J=7.8 Hz, 9-H), 8.18 (1H, s, 6′-H), 8.43 (1H, s, 2-H). ¹³C NMR (100 MHz, CDCl₃) δ: 19.61, 21.43, 32.36, 89.56, 99.71, 114.41, 122.94, 123.67, 127.89, 128.34, 131.89, 134.75, 135.01, 135.93, 136.75, 137.44, 139.84, 143.26, 144.00, 144.31, 150.87, 152.88. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₈N₅: 446.2586; found: 446.2589.

TBI-349, 5-(4-Methylphenyl)-3-cyclopropylimino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 0.80-0.86 (6H, m, —CH₂—CH—CH₂—), 2.54 (3H, s, —CH₃), 2.71 (1H, m, —CH₂—CH—CH₂—), 5.64 (1H, s, 4-H), 6.53 (1H, d, J=7.2 Hz, 6-H), 6.84 (1H, s, 1-H), 7.16-7.21 (2H, m, 7-H, 8-H), 7.24 (2H, d, 8.1 Hz, 2″-H, 6″-H), 7.30 (1H, m, 9-H), 7.51 (2H, d, J=8.1 Hz, 3″-H, 5″-H), 7.70 (1H, d, J=6.3 Hz, 4′-H), 7.77 (1H, d, J=7.5 Hz, 5′-H), 8.32 (1H, d, J=3.6 Hz, 6′-H), 8.56 (1H, s, 2′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 9.61, 21.43, 32.36, 89.56, 99.71, 114.41, 122.94, 123.67, 127.89, 128.34, 131.89, 134.75, 135.01, 135.93, 136.75, 137.44, 139.84, 143.26, 144.00, 144.31, 150.87, 152.88. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₄N₅: 418.2233; found: 418.2231.

TBI-350, 5-(3,4-Dichlorophenyl)-3-cyclohexylimino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.24-2.04 (10H, m, —CH₂—CH₂—CH₂—CH₂—CH₂—), 3.14 (1H, m, —CH₂—CH—CH₂—), 5.28 (1H, s, 4-H), 6.47 (1H, d, J=8.4 Hz, 6-H), 6.76 (1H, s, 1-H), 7.12-7.31 (4H, m, 7-H, 8-H, 5″-H, 6″-H), 7.50 (1H, s, 2″-H), 7.76 (1H, d, J=8.1 Hz, 4′-H), 7.75 (1H, d, J=7.8 Hz, 5′-H), 7.81 (1H, d, J=8.4 Hz, 9-H), 8.33 (1H, d, J=4.8 Hz, 6′-H), 8.57 (1H, d, J=2.1 Hz, 2′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 24.54, 25.81, 33.67, 57.94, 89.47, 99.45, 113.63, 123.20, 123.63, 127.82, 127.93, 128.44, 128.56, 131.08, 131.27, 132.99, 134.27, 134.46, 135.29, 135.56, 136.75, 143.70, 143.96, 144.33, 150.31, 151.00. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₆Cl₂N₅: 514.1720; found: 514.1719.

TBI-351, 5-(3,4-Dichlorophenyl)-3-(4-tetrahydropyranyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.52 (4H, m, —CH₂—CH—CH₂—), 3.42 (3H, m, —CH₂—CH—CH₂—), 3.97 (2H, m, —CH₂—CH—CH₂—), 5.27 (1H, s, 4-H), 6.49 (1H, d, J=7.8 Hz, 6-H), 6.84 (1H, s, 1-H), 7.14-7.33 (4H, m, 7-H, 8-H, 5″-H, 6″-H), 7.50 (1H, s, 2″-H), 7.70 (1H, d, J=7.2 Hz, 4′H), 7.75 (1H, d, J=7.2 Hz, 5′-H), 7.81 (1H, d, J=8.4 Hz, 9-H), 8.34 (1H, d, J=4.5 Hz, 6′-H), 8.59 (1H, s, 2′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 33.41, 54.31, 66.02, 89.02, 99.64, 113.77, 123.44, 123.68, 128.04, 128.14, 128.45, 128.57, 130.93, 131.18, 133.07, 134.47, 135.38, 135.57, 136.55, 136.65, 143.61, 144.04, 144.56, 150.67, 150.90. HRMS (ESI-TOF⁺): m/z [M+H]+ calcd for C₂₈H₂₄Cl₂N₅O: 516.1373; found: 516.1370.

TBI-352, 5-(3,4-Dichlorophenyl)-3-(4-methoxycyclohexyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.20-1.46 (4H, m, —CH₂—CH—CH₂—), 1.49-2.06 (4H, m, —CH₂—O—CH₂—), 3.14-3.20 (2H, —CH₂—CH—CH₂—, —CH₂—CH—CH₂—), 3.36 (3H, s, —OCH₃), 5.27 (1H, s, 4-H), 6.48 (1H, d, J=7.8 Hz, 6-H), 6.81 (1H, s, 1-H), 7.13-7.31 (4H, m, 7-H, 8-H, 5″-H, 6″-H), 7.49 (1H, s, 2″-H), 7.68 (1H, d, J=7.2 Hz, 4′-H), 7.75 (1H, s, 5′-H), 7.81 (1H, d, J=6.6 Hz, 9-H), 8.33 (1H, d, J=4.8 Hz, 6′-H), 8.57 (1H, s, 2′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 29.75, 29.88, 31.16, 55.85, 57.30, 78.42, 89.21, 99.57, 113.73, 123.31, 123.66, 127.97, 128.43, 131.16, 133.09, 134.54, 135.38, 135.56, 136.63, 143.57, 143.98, 144.42, 150.92. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₂₈Cl₂N₅O: 544.1173; found: 544.1172.

TBI-153, 5-(3,4-Dichlorophenyl)-3-(1-methylethyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.12 (6H, d, J=7.5 Hz, (CH₃)₂—CH—), 2.55 (3H, s, —CH₃), 3.51 (1H, m, (CH₃)₂—CH—), 5.29 (1H, s, 4-H), 6.44 (1H, d, J=7.5 Hz, 6-H), 6.69 (1H, s, 1-H), 7.11-7.23 (5H, m, 7-H, 8-H, 9-H, 5″-H, 6″-H), 7.49 (1H, s, 2″-H), 7.66 (1H, d, J=3.0 Hz, 4′-H), 7.82 (1H, d, J=3.0 Hz, 5′-H), 8.45 (1H, d, J=2.4 Hz, 2′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 23.53, 23.82, 49.48, 89.16, 98.86, 113.63, 123.17, 128.33, 128.57, 129.55, 131.06, 131.23, 133.09, 134.33, 134.52, 135.35, 136.82, 143.82, 144.45, 150.22, 150.96, 153.47. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₄Cl₂N₅: 488.1523; found: 488.1524.

TBI-354, 5-(3,4-Dichlorophenyl)-3-cyclohexylimino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.23-1.76 (10H, m, —CH₂—CH₂13 CH₂—CH₂—CH₂—), 2.56 (3H, s, —CH₃), 3.13 (1H, m, —CH₂—CH—CH₂—), 5.28 (1H, s, 4-H), 6.47 (1H, d, J=8.7 Hz, 6-H), 6.69 (1H, s, 1-H), 7.13-7.23 (5H, m, 7-H, 8-H, 9-H, 5″-H, 6″-H), 7.49 (1H, s, 2″-H), 7.66 (1H, d, J=6.3 Hz, 4′-H), 7.82 (1H, d, J=2.7 Hz, 5′-H), 8.45 (1H, d, J=2.4 Hz, 2′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 23.82, 24.60, 25.81, 33.68, 57.99, 89.47, 98.85, 113.61, 123.17, 127.61, 128.34, 128.58, 129.48, 131.00, 131.29, 132.97, 133.98, 134.22, 134.41, 135.26, 135.58, 136.82, 136.82, 143.78, 144.45, 150.38, 151.02, 153.43. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₂₈Cl₂N₅: 528.1736; found: 528.1735.

TBI-355, 5-(3,4-Dichlorophenyl)-3-(4-methoxycyclohexyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.20-1.50 (4H, m, —CH₂—CH—CH₂—), 1.70-2.06 (4H, m, —CH₂—CH—CH₂—), 2.55 (3H, s, py-CH₃), 3.10-3.23 (2H, m, —CH₂—CH—CH₂—, —CH₂—CH—CH₂), 3.34 (3H, s, —OCH₃), 5.27 (1H, s, 4-H), 6.48 (1H, d, J=7.2 Hz, 6-H), 6.69 (1H, s, 1-H), 7.13-7.21 (5H, m, 7-H, 8-H, 9-H, 5″-H, 6″-H), 7.48 (1H, s, 2″-H), 7.67 (1H, d, J=6.9 Hz, 4′-H), 7.82 (1H, d, J=2.7 Hz, 5′-H), 8.43 (1H, s, 2′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 23.83, 29.78, 29.92, 31.19, 55.84, 57.33, 89.20, 98.96, 113.70, 123.19, 127.74, 128.39, 128.44, 129.51, 130.96, 132.99, 133.90, 134.49, 135.34, 135.57, 136.65, 143.80, 144.34, 150.85, 150.98, 153.53. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₀Cl₂N₅O: 558.1885; found: 558.1884.

TBI-356, 5-(4-Methylphenyl)-3-(1-methylethyl)imino-2-(6-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.07 (6H, d, J=6.0 Hz, —CH—(CH₃)₂), 2.52 (3H, s, —CH₃), 3.34 (1H, m, —CH—(CH₃)₂), 3.39 (3H, s, —OCH₃), 5.30 (1H, s, 4-H), 6.46 (1H, s, 6-H), 6.48 (1H, s, 1-H), 6.75 (1H, d, J=8.4 Hz, 9-H), 7.04-7.12 (2H, m, 7-H, 8-H), 7.17 (2H, d, J=8.1 Hz, 2″-H, 6″-H), 7.47 (2H, J=8.1 Hz, 3″-H, 5″-H), 7.62 (1H, s, 4′-H), 7.65 (1H, s, 5′-H), 8.13 (1H, s, 2′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 21.43, 23.55, 49.25, 53.61, 88.98, 98.03, 110.96, 114.20, 122.56, 127.16, 127.93, 128.43, 130.36, 131.78, 135.08, 135.67, 139.63, 142.40, 145.95, 150.74, 151.02, 161.13. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₈N₅O: 450.2332: found: 450.2330.

TBI-357, 5-(4-Methylphenyl)-3-cyclohexylimino-2-(6-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.09-1.95 (10H, m, —CH₂—CH₂—CH₂—CH₂—CH₂—), 2.53 (3H, s, —CH₃), 3.06 (1H, m, —CH2-CH—CH₂), 3.95 (3H, s, —OCH₃), 5.27 (1H, s, 4-H), 6.49 (1H, s, 1-H), 6.52 (1H, d, J=9.3 Hz, 6-H), 6.76 (1H, d, J=8.7 Hz, 9-H), 7.06-7.13 (2H, m, 7-H, 8-H), 7.18 (2H, d, J=7.8 Hz, 2″-H, 6″-H), 7.49 (2H, J=7.8 Hz, 3″-H, 5″-H), 7.62-7.66 (2H, m, 4′-H, 5′-H), 8.13 (1H, d, J=2.1 Hz, 2′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 21.35, 24.70, 25.89, 33.62, 53.60, 57.87, 89.30, 98.01, 110.94, 114.17, 122.54, 127.15, 127.93, 128.43, 130.39, 131.67, 135.00, 135.71, 139.59, 142.33, 145.94, 150.89, 151.06. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₂N₅O: 490.4490; found: 490.4489.

TBI-358, 5-(4-Methylphenyl)-3-(4-methoxycyclohexyl)imino-2-(6-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.09-1.45 (4H, m, —CH₂—CH—CH₂—), 1.68-1.72 (2H, m, —CH₂—CH—CH₂—), 2.02-2.07 (2H, m, —CH₂—CH—CH₂—), 2.53 (3H, s, —CH₃), 3.03-3.21 (2H, m, —CH₂—CH—CH₂—, —CH—CH—CH₂—), 3.35 (3H, s, py-OCH₃), 3.95 (3H, s, —OCH₃), 5.28 (1H, s, 4-H), 6.50 (1H, s, 1-H), 6.53 (1H, s, 6-H), 6.77 (1H, d, J=8.7 Hz, 9-H), 7.07-7.14 (2H, m, 7-H, 8-H), 7.18 (2H, d, J=8.1 Hz, 2″-H, 6″-H), 7.48 (2H, J=8.1 Hz, 3″-H, 5″-H), 7.62-7.66 (2H, m, 4′-H, 5′-H), 8.13 (1H, d, J=2.1 Hz, 2′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 21.43, 30.01, 31.17, 53.61, 55.84, 57.28, 78.66, 89.03, 98.13, 110.97, 114.26, 122.64, 127.28, 127.99, 128.33, 130.26, 131.70, 134.91, 135.70, 135.70, 139.81, 142.37, 145.81, 150.90, 151,47, 161.16. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₂H₃₄N₅O₂: 520.2752; found: 520.2751.

TBI-359, 5-(3,4-Dichlorophenyl)-3-(1-methylethyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.13 (6H, d, J=6.3 Hz, —CH—(CH₃)₂), 3.50 (1H, m, —CH—(CH₃)₂), 4.03 (3H, s, —OCH₃), 5.29 (1H, s, 4-H), 6.43 (1H, d, J=6.3 Hz, 6-H), 6.89 (1H, s, 1-H), 6.93 (1H, m, 9-H), 7.10-7.23 (3H, m, 8-H, 5″-H), 7.49 (1H, d, J=2.4 Hz, 2″-H), 7.68 (1H, m, 6″-H), 7.80-7.84 (3H, m, 4′-H, 5′-H, 6′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 23.57, 49.49, 53.74, 89.33, 100.12, 113.62, 116.80, 123.10, 124.79, 125.02, 127.68, 128.33, 131.26, 134.28, 134.47, 135.32, 135.55, 136.84, 138.96, 142.95, 150.40, 151.24, 155.51. HRMS (ESI-TOF⁺): m/z calcd for C₂₇H₂₄Cl₂N₅O: 504.1853; found: 504.1852.

TBI-360, 5-(4-Methylphenyl)-3-(4-tetrahydropyranyl)imino-2-(6-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (CDCl₃) δ: 1.60-1.67 (4H, —CH₂—CH—CH₂—), 2.54 (3H, s, —CH₃), 3.34-3.42 (3H, m, —CH₂—CH—CH₂—), 3.95 (3H, s, —OCH₃), 3.98 (2H, m, —CH₂—CH—CH₂—), 5.26 (1H, s, 4-H), 6.52 (1H, s, 1-H), 6.55 (1H, m, 6-H), 6.78 (1H, m, 9-H), 7.11-7.17 (2H, m, 7-H, 8-H), 7.20 (2H, d, J=7.8 Hz, 2″-H, 6″-H), 7.50 (2H, J=7.8 Hz, 3″-H, 5″-H), 7.62-7.68 (2H, m, 4′-H, 5′-H), 8.14 (1H, m, 2′-H). ¹³C NMR (CDCl₃) δ: 21.37, 33.42, 53.63, 54.34, 66.22, 88.88, 98.20, 111.03, 114.30, 122.77, 127.37, 128.07, 128.37, 130.18, 131.59, 131.73, 134.97, 135.21, 135.72, 139.78, 142.48, 145.87, 150.76, 151.47. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₃₀N₅O₂: 492.2514; found: 492.2513.

TBI-361, 5-(3,4-Dichlorophenyl)-3-(4-tetrahydropyranyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.61-1.72 (4H, m, —CH₂—CH—CH₂—), 3.48-3.52 (3H, m, —CH₂—CH—CH₂—), 4.04 (5H, m, —OCH₃), 5.26 (1H, s, 4-H), 6.47 (1H, d, J=7.8 Hz, 6-H), 6.90-6.94 (1H, m, 9-H), 6.95 (1H, s, 1-H), 7.13-7.23 (3H, m, 7-H, 8-H, 5″-H), 7.49 (1H, s, 2″-H), 7.70 (1H, d, J=7.2 Hz, 6″-H), 7.81-7.85 (3H, m, 4′-H, 5′-H, 6′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 3.31, 53.28, 53.78, 65.50, 89.06, 100.32, 113.72, 116.83, 123.33, 124.38, 127.89, 128.44, 128.50, 131.03, 131.21, 134.41, 134.67, 135.36, 135.57, 136.69, 138.82, 142.63, 150.94, 155.31. HRMS (ESI-TOF⁺): calcd for C₂₉H₂₆Cl₂N₅O₂: 546.1875: found: 546.1874.

TBI-362, 5-(3,4-Dichlorophenyl)-3-(4-methoxycyclohexyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.23-1.51 (4H, m, —CH₂—CH—CH₂—), 1.73-2.10 (4H, m, —CH₂—CH—CH₂—), 3.15-3.29 (2H, m, —CH₂—CH—CH₂—, —CH₂—CH—CH₂—), 3.37 (3H, s, —OCH₃), 3.78 (3H, s, —OCH₃), 527 (1H, s, 4-H), 6.48 (1H, d, J=8.4 Hz, 6-H), 6.90-6.93 (2H, m, 9-H, 1-H), 7.12-7.24 (3 D, m, 7-H, 8-H, 5″-H), 7.49 (1H, d, J=2.1 Hz, 2″-H), 7.70 (1H, d, J=7.2 Hz, 6″-H), 7.79-7.84 (3H, m, 4′-H, 5′-H, 6′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 29.25, 29.37, 30.73, 53.72, 55.81, 56.81, 89.34, 100.23, 113.67, 116.82, 123.19, 124.66, 124.78, 127.80, 128.49, 131.14, 131.21, 134.39, 134.48, 135.33, 135.56, 136.65, 138.83, 142.73, 151.06, 151.12, 155.36. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₀Cl₂N₅O₂: 574.2129: found: 574.2128.

TBI-363, 5-(2,4-Dichlorophenyl)-3-(1-methylethyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.24 (6H, d, J=6.9 Hz, —CH—(CH₃)₂), 3.50 (1H, m, —CH—(CH₃)₂), 5.20 (1H, s, 4-H), 6.36 (1H, d, J=7.5 Hz, 6-H), 6.83 (1H, s, 1-H), 7.13-7.22 (2 m, 7-H, 8-H), 7.28-7.36 (2H, m, 5″-H, 6″-H), 7.61 (1H, d, J=8.1 Hz, 4′-H), 7.70 (1H, d, J=8.4 Hz, 5′-H), 7.77 (1H, s, 9-H), 7.79 (1H, s, 2″-H), 8.33 (1H, d, 3.6 Hz, 6″-H), 8.95 (1H, s, 2′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 23.37, 23.58, 49.50, 88.82, 99.66, 113.19, 123.32, 123.67, 128.11, 128.52, 130.02, 131.74, 131.93, 133.29, 133.46, 134.71, 135.61, 136.72, 143.72, 144.03, 144.36, 150.45, 151.00. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₆H₂₂Cl₂N₅: 474.1259; found: 474.1257.

TBI-164, 5-(4-Trifluoromethoxyphenyl)-3-cyclopropylimino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 0.82-0.89 (4H, m, —CH₂—CH₂—), 2.71 (1H, m, —CH₂—CH—CH₂—), 4.08 (3H, s, —OCH₃), 5.49 (1H, s, 4-H), 6.41 (1H, d, J=7.8 Hz, 6-H), 6.87 (1H, s, 1-H), 6.90-6.92 (1H, m, 9-H), 7.09-7.18 (2H, m, 7-H, 8-H), 7.43 (2H, d, J=8.1 Hz, 2″-H, 6″-H), 7.58 (2H, d, J=8.1 Hz, 3″-H, 3″-H), 7.68 (1H, d, J=7.2 Hz, 4′-H), 7.79-7.83 (2H, m, 5′-H, 6′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 10.02, 32.85, 53.69, 89.69, 100.07, 113.17, 116.82, 119.11, 121.69, 122.96, 123.63, 124.69, 125.11, 127.66, 128.20, 130.91, 131.70, 134.68, 135.72, 135.91, 138.92, 142.65, 149.66, 151.42, 152.63, 155.46. HRMS (ESI-TOF⁺): [M+H]⁺ calcd for C₂₈H₂₃F₃N₅O₃: 518.3705; found: 518.3702.

TBI-365, 5-(4-Trifluoromethoxyphenyl)-3-cyclohexylimino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.11-1.77 (10H, m, —CH₂—CH₂—CH₂—CH₂—CH₂—), 3.07 (1H, m, —CH₂—CH—CH₂—), 4.02 (3H, s, —OCH₃), 5.18 (1H, s, 4-H), 6.47 (1H, d, J=7.2 Hz, 6-H), 6.88 (1H, s, 1-H), 6.90-6.92 (1H, m 9-H), 7.11-7.19 (2H, m, 7-H, 8-H), 7.41 (2H, d, J=8.1 Hz, 2″-H, 6″-H), 7.58 (2H, d, J=8.1 Hz, 3″-H, 5″-H), 7.70 (1H, d, J=8.1 Hz, 4′-H), 7.79-7.84 (2H, m, 5′-H, 6′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 24.35, 25.92, 33.54, 53.70, 57.69, 89.54, 100.09, 113.68, 116.79, 122.91, 123.80, 124.62, 124.90, 127.65, 128.26, 130.83, 131.50, 134.80, 135.61, 136.06, 138.71, 142.86, 150.63, 151.32, 155.40. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₂₉F₃N₅O₂: 560.3973; found: 560.3972.

TBI-366, 5-(3,4-Dichlorophenyl)-3-cyclopropylimino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 0.86-0.96 (4H, m, —CH₂—CH₂—), 2.80 (1H, m, —CH₂—CH₂—CH₂—), 4.00 (3H, s, —OCH₃), 5.54 (1H, s, 4-H), 6.41 (1H, d, J=8.7 Hz, 6-H), 6.86 (1H, s, 1-H), 6.91 (1H, m, 9-H), 7.10-7.28 (3H, m, 7-H, 8-H, 5″-H), 7.51 (1H, d, J=2.1 Hz, 2″-H), 7.65 (1H, m, 6″-H), 7.80-7.83 (3H, m, 4′-H, 5′-H, 6′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 33.07, 53.70, 89.75, 100.04, 113.57, 116.80, 123.10, 124.65, 125.15, 127.66, 128.23, 128.76, 131.38, 133.17, 134.31, 135.35, 135.65, 136.83, 138.97, 142.67, 151.42, 152.23, 155.44. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₂Cl₂N₅O: 502.1317; found: 502.1316.

TBI-367, 5-(2,4-Dichlorophenyl)-3-cyclopropylimino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 0.84-0.94 (4H, m, —CH₂—CH₂—), 2.77 (1H, m, —CH₂—CH—CH₂—), 5.46 (1H, s, 4-H), 6.33 (1H, d, J=7.5 Hz, 6-H), 6.78 (1H, s, 1-H), 6.78-7.16 (2H, m, 7-H, 8-H), 7.27-7.31 (2H, m, 5″-H, 6″-H), 7.37 (1H, d, J=8.1 Hz, 4′-H), 7.60 (1H, d, J=8.4 Hz, 5′-H), 7.68 (1H, s, 9-H), 7.79 (1H, s, 2″-H), 8.33 (1H, d, J=3.6 Hz, 6′-H), 8.54 (1H, s, 2′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 10.13, 33.05, 89.21, 99.57, 113.13, 123.26, 123.68, 127.97, 128.28, 130.04, 130.43, 131.89, 132.06, 133.34, 134.71, 135.70, 136.57, 143.52, 144.13, 144.48, 151.29, 152.26. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₆H₂₀Cl₂N₅: 472.1149; found: 472.1146.

TBI-368, 5-(2,4-Dichlorophenyl)-3-cyclohexylimino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.18-1.77 (10H, m, —CH₂—CH₂—CH₂—CH₂—CH₂—), 3.12 (1H, m, —CH₂—CH—CH₂—), 5.16 (1H, s, 4-H), 6.38 (1H, d, J=7.5 Hz, 6-H), 6.82 (1H, s, 1-H), 7.13-7.22 (2H, m, 7-H, 8-H), 7.27-7.31 (2H, m, 5″-H, 6″-H), 7.59 (1H, d, J=8.1 Hz, 4′-H), 7.62 (1H, d, J=8.41 Hz, 5′-H), 7.68 (1H, s, 9-H), 7.79 (1H, s, 2″-H), 8.33 (1H, d, J=3.6 Hz, 6″-H), 8.56 (1H, s, 2″-H). ¹³C NMR (100 MHz, CDCl₃) δ: 24.57, 25.82, 33.49, 33.68, 57.95, 89.09, 99.59, 113.15, 123.25, 123.64, 127.97, 128.49, 129.92, 130.32, 131.82, 122.35, 134.72, 135.60, 136.58, 136.74, 143.74, 143.98, 144.32, 150.50, 151.12. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₆Cl₂N₅: 514.1608; found: 514.1606.

TBI-369, 5-(2,4-Dichlorophenyl)-3-(1-methylethyl)imino-2-(2-ethoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.16 (6H, d, J=6.9 Hz, —CH—(CH₃)₂), 3.49 (1H, m, —CH—(CH₃)₂), 3.79 (3H, s, —OCH₃), 5.19 (1H, s, 4-H), 6.35 (1H, d, J=7.8 Hz, 6-H), 6.89-6.93 (2H, m, 1-H, 9-H), 7.11-7.21 (2H, m, 7-H, 8-H), 7.35 (1H, d, J=8.4 Hz), 7.58-7.61 (1H, m), 7.68-7.61 (1H, m), 7.79-7.85 (3H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 23.40, 23.62, 49.51, 53.71, 89.01, 100.17, 113.10, 116.79, 123.16, 124.76, 125.14, 127.81, 128.36, 129.98, 130.42, 131.83, 131.91, 134.79, 135.58, 136.55, 128.94, 142.99, 150.65, 151.35, 155.54. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₄Cl₂N₅O: 504.1353; found: 504.1351.

TBI-370, 5-(2,4-Dichlorophenyl)-3-cyclopropylimino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 0.86-0.94 (4H, m, —CH₂—CH₂—), 2.78 (1H, m, —CH₂—CH—CH₂), 3.81 (3H, s, —OCH₃), 5.45 (1H, s, 4-H), 6.32 (1H, d, J=7.8 Hz, 6-H), 6.87-6.92 (2H, m, 1-H, 9-H), 7.11-7.20 (2H, m, 7-H, 8-H), 7.35 (1H, d, J=18.4 Hz), 7.36-7.89 (1H, m), 7.66-7.69 (1H, m), 7.78-7.83 (3H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 10.18, 10.27, 33.06, 53.70, 89.38, 100.11, 113.07, 116.82, 123.16, 124.67, 125.30, 127.80, 130.02, 130.53, 132.01, 133.25, 133.41, 134.41, 135.71, 136.49, 138.99, 142.76, 151.57, 152.47, 155.50. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₂Cl₂N₅O: 502.1223; found: 502.1220.

TBI-371, 5-(2,4-Dichlorophenyl)-3-(4-methoxycyclohexyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.24-2.07 (8H, m, —CH₂—CH₂—, —CH₂—CH₂—), 3.16-3.34 (2H, m, —CH—CH₂—CH—), 3.37 (3H, s, —OCH3), 4.00 (3H, m, —OCH3), 5.17 (1H, s, 4-H), 6.37 (1H, d, J=7.8 Hz, 6-H), 6.89-6.93 (2H, m, 1-H, 9-H), 7.13-7.22 (2H, m, 7-H, 8-H), 7.33 (1H, d, J=8.4 Hz), 7.57-7.61 (1H, m), 7.69-7.72 (1H, m), 7.78-7.85 (3H, m), ¹³C NMR (100 MHz, CDCl₃) δ: 29.37, 30.53, 30.79, 53.17, 55.82, 56.87, 78.22, 89.00, 100.31, 113.19, 116.84, 123.25, 124.83, 127.94, 128.42, 129.94, 130.37, 131.76, 131.84, 133.26, 134.67, 125.62, 136.71, 138.86, 142.82, 151.29. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₀Cl₂N₅O₂: 574.1935; found: 574.1793.

TBI-372, 5-(4-Trifluoromethoxyphenyl)-3-(1,3-dimethoxyisopropyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 3.26 (6H, s, —OCH₃, —OCH₃), 3.34-3.39 (2H, m, —CH—CH₂—), 3.52-3.57 (2H, m, —CH—CH₂—), 3.68-3.72 (1H, m, —CH₂—CH—CH₂—), 4.01 (3H, s, —OCH₃), 5.49 (1H, s, 4-H), 6.52 (1H, d, J=7.2 Hz, 6-H), 6.89-6.96 (2H, m, 1-H, 9-H), 7.12-7.20 (4H, m, 7-H, 8-H, 2″-H, 6″-H), 7.48 (2H, d, J=7.8 Hz, 3″-H, 5″-H), 7.79-7.86 (2H, m, 4′-H, 5′-H), 8.43 (1H, s, 6′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 53.65, 58.55, 59.00, 74.42, 90.24, 100.20, 113.86, 123.09, 123.52, 124.76, 124.94, 126.80, 127.82, 128.36, 130.81, 131.48, 135.64, 135.83, 138.90, 142.72, 149.74, 150.95, 153.46, 155.42. HRMS (ESI-TOF⁺): m/z [M+F]⁺ calcd for C₃₀H₂₉F₃N₅O₄: 580.2252; found: 580.2249.

TBI-373, 5-(4-Methylphenyl)-3-(1,3-dimethoxyisopropyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 2.50 (3H, s, —CH₃), 3.24 (6H, s, —OCH₃, —OCH₃), 3.54 (3H, s, —OCH₃), 3.33-3.38 (2H, m, —CH—CH₂—), 3.50-3.55 (2H, m, —CH—CH₂—), 3.67-3.72 (1H, m, —CH₂—CH—CH₂—), 5.48 (1H, s, 4-H), 6.50 (1H, d, J=7.8 Hz, 6-H), 6.73 (1H, s, 1-H), 7.13-7.16 (3H, m, 7-H, 841, 9-H), 7.23 (2H, d, J=7.8 Hz, 2″-H, 6′-H), 7.47 (2H, d, J=7.8 Hz, 3″-H, 5″-H), 7.67-7.68 (1H, m, 6′-H), 7.80 (2H, m, 4′-H, 5′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 21.36, 23.82, 58.21, 58.98, 74.28, 89.71, 98.99, 114.39, 122.79, 123.15, 127.59, 128.15, 128.38, 129.56, 131.79, 134.03, 134.84, 135.13, 135.68, 139.81, 143.89, 144.32, 150.69, 153.33, 153.46. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₃₂N₅O₃: 510.2511; found: 510.2510.

TBI-374, 5-(4-Methylphenyl)-3-(1,3-dimethoxyisopropyl)imino-2-(6-ethyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 2.28 (3H, s, —CH₃), 3.01 (3H, s, —CH₃), 3.30 (6H, s, —OCH₃, —OCH₃), 3.36-3.44 (2H, m, —CH—CH₂—), 3.55-3.57 (2H, m, —CH—CH₂—), 3.72-3.76 (1H, m, —CH₂—CH—CH₂—), 5.49 (1H, s, 4-H), 6.49 (1H, d, J=8.4 Hz, 6-H), 6.73 (1H, s, 1-H), 7.14-7.17 (3H, m, 7-H, 8-H, 9-H), 7.23 (2H, d, J=7.8 Hz, 2″-H, 6″-H), 7.47 (2H, d, J=7.8 Hz, 3″-H, 5″-H), 7.67-7.68 (1H, m, 2′-H), 7.80 (2H, m, 4′-H, 5′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 21.26, 23.72, 58.31, 58.98, 74.28, 89.71, 99.99, 114.75, 123.22, 127.86, 128.42, 128.58, 131.58, 134.03, 134.84, 135.32, 135.68, 139.81, 143.23, 144.32, 150.69, 153.33, 153.46. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₃₂N₅O₂: 494.2555; found: 494.2553.

TBI-375, 5-(3,4-Dichlorophenyl)-3-(1,3-dimethoxyisopropyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 3.28 (3H, s, —OCH₃), 3.30 (6H, s, —OCH₃, —OCH₃), 3.36-3.44 (2H, m, —CH—CH₂—), 3.55-3.57 (2H, m, —CH—CH₂—), 3.72-3.76 (1H, —CH₂—CH—CH₂—), 5.49 (1H, s, 4-H), 6.49 (1H, d, 18.4 Hz, 6-H), 6.89-6.93 (2H, m, 1-H, 9-H), 7.15-7.22 (3H, m, 7-H, 8-H, 5″-H), 7.49 (1H, d, J=2.4 Hz, 2″-H), 7.70 (1H, m, 6″-H), 7.78-7.84 (3H, m, 4′-H, 5′-H, 6′-H). ¹³C NMR (100 MHz, CDCl₃) δ: 53.67, 58.82, 59.10, 59.19, 74.48, 74.73, 90.59, 100.23, 113.75, 116.81, 123.22, 124.72, 125.00, 127.86, 128.42, 128.58, 131.58, 133.04, 135.32, 138.70, 138.94, 142.73, 150.95, 153.41, 155.44. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₉Cl₂N₅O₃: 564.1578; found: 564.1577.

TBI-157, 5-(4-Trifluoromethoxyphenyl)-3-(1-methylethyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.08-1.20 (d, J=6.6 Hz, 6H), 3.38-3.45, J=6.3 Hz, 1H), 5.23 (s, 1H), 6.45 (m, 2H), 6.83 (s, 1H), 7.12-7.18 (m, 2H), 7.40-7.42 (m, 2H), 7.57-7.60 (m, 2H), 7.78 (1H, m), 8.33-8.35 (2H, m), 8.58 (1H, s). ¹³C NMR (100 MHz, CDCl₃) δ: 23.48, 49.44, 89.12, 99.41, 113.78, 123.06, 123.63, 127.79, 127.95, 128.37, 130.79, 131.45, 134.94, 135.60, 135.90, 136.77, 143.68, 143.98, 144.32, 149.73, 150.35, 150.95. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₃F₃N₅O: 490.1870; found: 490.1869.

TBI-158, 5-(4-Trifluoromethoxyphenyl)-3-(N-isobutyl-4-piperidyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 0.87-0.93 (d, J=6.0 Hz, 6H), 1.47-1.86 (m, 5H), 2.04 (brs, 4H), 2.78 (m, 2H), 3.07 (m, 1H), 5.19 (s, 1H), 6.52 (m, 1H), 6.85 (s, 1H), 7.19 (m, 2H), 7.26-7.32 (m, 1H), 7.40-7.43 (m, 2H), 7.59-7.62 (m, 2H), 7.70-7.72 (m, 1H), 7.76-7.79 (m, 1H), 8.33-8.34 (m, 1H), 8.59 (brs, 1H). ¹³C NMR (100 MHz, CDCl₃) δ: 20.97, 25.68, 32.28, 45.59, 52.49, 56.37, 67.04, 89.28, 99.45, 113.82, 123.15, 123.67, 123.90, 127.91, 128.46, 131.27, 134.95, 135.96, 136.70, 143.57, 143.96, 144.37, 149.75, 150.94. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₃H₃₄F₃N₆O: 587.2854; found: 587.2856.

TBI-159, 5-(4-Trifluoromethoxyphenyl)-3-(N-methyl-4-piperidyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.62-1.74 (m, 4H), 1.89-195 (m, 2H), 2.6 (s, 3H), 2.77-2.80 (m, 2H), 3.06 (m, 1H), 5.17 (s, 1H), 6.50-6.52 (d, J=7.2 Hz, 1H), 6.84 (s, 1H), 7.14-7.19 (m, 2H), 7.30-7.32 (m, 1H) 7.40-7.43 (d, J=8.4 Hz, 2H), 7.59-7.62 (d, J=8.4 Hz, 2H), 7.70-7.73 (m, 1H), 7.76-7.79 (m, 1H), 8.33-8.35 (m, 1H), 8.60 (brs, 1H). ¹³C NMR (100 MHz, CDCl₃) δ: 32.79, 46.39, 53.40, 54.19, 89.19, 99.43, 113.80, 123.17, 123.64, 123.93, 127.90, 128.02, 128.46, 130.75, 131.28, 134.98, 135.63, 136.00, 136.65, 143.60, 144.41, 149.72, 150.83, 151.10, HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₂₈F₃N₆O: 545.2368; found: 545.2370.

TBI-160, 5-(4-Trifluoromethoxyphenyl)-3-(2-morpholinoethyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 2.47-2.50 (t, J=4.5 Hz, 4H), 2.70-2.75 (t, J=6.6 Hz, 2H), 3.35-3.39 (t, J=6.6 Hz, 2H), 3.68-3.71 (t, J=4.5 Hz, 4H), 5.36 (s, 1H), 6.57-6.59 (d, J=7.8 Hz, 1H), 7.00 (s, 1H), 7.27-7.35 (m, 3H), 7.43-7.46 (m, 2H), 7.61-7.64 (m, 1H), 7.79-7.84 (m, 2H), 8.36-8.38 (m, 1H), 8.64-8.65 (m, 1H). ¹³C NMR (100 MHz, CDCl₃) δ: 46.23, 53.72, 58.51, 66.66, 88.95, 100.75, 114.44, 123.68, 123.82, 124.26, 128.75, 128.89, 130.35, 130.82, 135.04, 135.30, 136.26, 136.67, 143.12, 144.03, 144.59, 149.60, 150.05, 153.02. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₂₈F₃N₆O₂: 561.2633; found: 561.2630.

TBI-161, 5-(4-Trifluoromethoxyphenyl)-3-(4-tetrahydropyranyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.57-1.69 (5 m), 3.28-3.39 (3H, m), 3.95-4.00 (1H, m), 5.18 (1H, s), 6.50-6.53 (1H, m), 6.86 (1H, s), 7.15-7.20 (2H, m), 7.29-7.33 (1H, m), 7.40-7.43 (2H, m), 7.59-7.62 (2H, m), 7.71-7.79 (2H, m), 8.34-8.36 (1H, m), 8.59-8.60 (1H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 33.41, 54.72, 66.21, 88.98, 99.57, 113.87, 123.69, 123.67, 123.90, 128.01. 128.09, 128.51, 130.72, 131.21, 135.09, 135.63, 135.93, 136.60, 143.59, 144.00, 149.76, 150.67, 151.12. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₅F₃NO₂: 532.1976; found: 532.1978.

TBI-162, 5-(4-Trifluoromethoxyphenyl)-3-(4-methoxycyclohexyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.09-1.20 (2H, m), 1.37-1.44 (2H, m), 1.67-1.71 (2H, m), 2.05-2.08 (2H, m), 3.07 (1H, m), 3.16 (1H, m), 3.36 (3 s), 5.20 (1H, s), 6.49 (2H, m), 6.84 (1H, s), 7.12-7.18 (2H, m), 7.40-7.43 (2H, m), 7.58-7.61 (2H, m), 7.79 (1H, m), 8.33-8.35 (2H, m), 8.58 (1H, s). HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₂₉F₃N₅O₂: 560.2257; found: 560.2259.

TBI-163, 5-(4-Trifluoromethoxyphenyl)-3-(N-cyclopentyl-4-piperidyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.43-1.58 (4H, m), 1.68 (6H, m), 1.86 (2H, m), 2.01 (2H, m), 2.46-2.51 (1H, m), 2.93-2.97 (2H, m), 3.11 (1H, m), 5.30 (1H, s), 6.50-6.52 (1H, d), 6.85 (1H, s), 7.15-7.23 (2H, m), 7.27-7.33 (1H, m), 7.41-7.43 (2H, d), 7.59-7.62 (2H, d), 7.70-7.78 (2H, m), 8.33-8.35 (1H, d), 8.57-8.58 (1H, m). HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₄H₃₄F₃N₆O: 599.2705; found: 599.2702.

TBI-164, 5-(4-Trifluoromethoxyphenyl)-3-(1-methylethyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.08-1.11 (6H, d, J=6.6 Hz), 3.38-3.47 (1H, m, J=6.3 Hz), 4.03 (3H, s), 5.22 (1H, s), 6.42-6.45 (1H, m), 6.89-6.93 (2H, m), 7.10-7.23 (2H, m), 7.39-7.42 (2H, m), 7.57-7.59 (2H, m), 7.68-7.71 (1H, m), 7.80-7.85 (2H, m), 8.92 (1H, brs). ¹³C NMR (100 MHz, CDCl₃)₆: 23.47, 49.23, 53.70, 89.30, 100.08, 113.71, 116.77, 122.93, 123.61, 124.81, 124.92, 127.64, 128.25, 130.84, 131.54, 134.84, 135.60, 135.96, 138.85, 142.89, 149.68, 150.60, 151.23, 155.48. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₅F₃N₅O₂: 520.1921; found: 520.1909.

TBI-165, 5-(4-Trifluoromethoxyphenyl)-3-(N-isobutyl-4-piperidyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 0.83-0.91 (6H, d, J=−6.3 Hz), 1.63-1.80 (5H, m), 1.94 (2H, m), 2.05-2.07 (2H, m), 2.75-2.79 (2H, m), 3.11 (1H, brs), 4.03 (3H, s), 5.18 (1H, s), 6.47-6.49 (1H, m), 6.89-6.93 (2H, m), 7.10-7.23 (2H, m), 7.39-7.42 (2H, m), 7.57-7.59 (2H, m), 7.68-7.71 (1H, m), 7.80-7.85 (2H, m), 8.92 (1H, brs). ¹³C NMR (100 MHz, CDCl₃) δ: 21.06, 25.68, 32.78, 52.21, 53.71, 55.65, 67.32, 89.32, 100.14, 113.74, 116.80, 119.15, 123.02, 124.40, 124.88, 127.72, 128.33, 130.80, 131.44, 134.92, 135.64, 136.02, 138.69, 142.71, 149.68, 151.01, 151.21, 155.33. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₄H₃₆F₃N₆O₂: 617.3442; found: 617.3443.

TBI-166, 5-(4-Trifluoromethoxyphenyl)-(4-methoxycyclohexyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.14-1.25 (2H, m), 1.38-1.49 (2H, m), 1.68-1.72 (2H, m), 2.04-2.08 (2H, m), 3.06-3.13 (1H, m), 3.19-3.26 (1H, m), 3.35 (3H, m), 4.02 (3H, s), 5.19 (1H, s), 6.47-6.49 (1H, m), 6.89-6.93 (2H, m), 7.12-7.21 (2H, m), 7.39-7.42 (2H, m), 7.57-7.59 (2H, m), 7.69-7.71 (1H, m), 7.80-7.85 (2H, m), 8.92 (1H, brs). ¹³C NMR (100 MHz, CDCl₃) δ: 29.44, 30.78, 53.71, 55.74, 56.95, 78.28, 89.29, 100.20, 113.78, 116.82, 123.02, 123.67, 124.65, 124.82, 127.77, 128.31, 130.76, 131.47, 134.88, 135.63, 135.87, 138.78, 142.73, 149.73, 151.14, 151.23, 155.36. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₂H₃₁F₃N₅O₃: 590.2978; found: 590.2977.

TBI-167, 5-(4-Trifluoromethoxyphenyl)-3-(4-tetrahydropyranyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.65-1.67 (4H, m), 3.35-3.48 (4H, m), 3.97-4.02 (1H, m), 4.03 (3H, s), 5.18 (1H, s), 6.48-6.51 (1H, m), 6.90-6.93 (2H, m), 7.16-7.21 (2H, m), 7.40-7.43 (2H, m), 7.59-7.62 (2H, m), 7.72-7.74 (1H, m), 7.81-7.86 (2H, m), 9.03 (1H, brs). ¹³C NMR (100 MHz, CDCl₃) δ: 33.23, 53.76, 53.82, 65.79, 89.05, 100.27, 113.82, 116.82, 123.17, 123.84, 124.48, 124.79, 127.86, 128.40, 130.76, 131.33, 135.06, 135.65, 135.95, 138.83, 142.66, 149.72, 150.96, 151.22, 155.34. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₂₇F₃N₅O₃: 562.2109: found: 562.2107.

TBI-168, 5-(4-Trifluoromethoxyphenyl)-3-(N-methyl-4-piperidyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 1.68-1.69 (4H, m), 2.07 (2H, brs), 2.30 (3H, s), 2.77-2.81 (2H, m), 3.15 (1H, s), 4.03 (3H, s), 5.17 (1H, s), 6.47-6.50 (1H, m), 6.89-6.95 (2H, m), 7.13-7.22 (2H, m), 7.39-7.42 (2H, m), 7.58-7.61 (2H, m), 7.70-7.73 (1H, m), 7.80-7.85 (2H, m), 9.06 (1H, brs). HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₀F₃N₆O₂: 575.2443; found: 575.2446.

TBI-169, 5-(4-Trifluoromethoxyphenyl)-3-(2-morpholinoethyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 2.24-2.32 (4H, m), 2.46-2.54 (2H, m), 2.72-2.77 (2H, m), 3.31-3.36 (2H, m), 3.69-3.72 (2H, m), 4.03 (3H, s), 5.23 (1H, s), 6.49 (2H, m), 6.84 (1H, s), 7.12-7.18 (2H, m), 7.39-7.42 (2H, m), 7.56-7.59 (2H, m), 7.75 (1H, m), 7.81-7.86 (2H, m). HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₀F₃N₆O₃: 591.2479; found: 591.2481.

TBI-1001, 5-(4-Fluorophenyl)-3-(4-methoxycyclohexyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.44 (1H, dd, J=2.1 Hz), 7.69 (2H, m), 7.42 (2H, t, J=8.4 Hz), 7.32 (2H, dd, J=8.7, 4.5 Hz), 7.16 (3H, m), 6.72 (1H, s), 6.48 (1H, dd, J=7.5 Hz, 1.8 Hz), 5.25 (1H, s), 3.36 (3H, s), 3.08 (1H, m), 3.07 (1H, m), 2.56 (3H, s), 2.06 (2H, 1.70 (2H, m), 1.43 (2H, m), 1.13 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 162.7, 153.4, 151.2, 150.9, 144.3, 143.7, 135.7, 135.1, 134.0, 133.4, 131.6, 130.8, 130.7, 129.4, 128.3, 127.7, 123.0, 118.4, 113.9, 98.9, 89.1, 78.5, 65.5, 55.8, 31.2, 30.0, 23.8. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₁FN₅O: 508.2513; found: 508.2512.

TBI-1002, 5-(4-Fluorophenyl)-3-(4-methoxycyclohexyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.92 (1H, s), 7.85 (1H, d, J=7.5 Hz), 7.81 (1H, d, J=4.8 Hz), 7.70 (1H, dd, J=7.5 Hz, 1.2 Hz), 7.42 (2H, t, J=8.4 Hz), 7.32 (2H, dd, J=8.4 Hz, 4.8 Hz), 7.16 (2H, m), 6.94 (1H, s), 6.90 (1H, dd, J=7.5 Hz, 2.7 Hz), 6.48 (1H, dd, J=7.5 Hz, 1.5 Hz), 5.24 (1H, s), 4.03 (3H, s), 3.37 (3H, s), 3.25 (1H, m), 3.12 (1H, m), 2.08 (2H, m), 1.72 (2H, m), 1.43 (2H, m), 1.23 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8, 155.4, 151.3, 151.2, 142.7, 138.7, 135.7, 135.1, 133.4, 131.8, 130.9, 130.8, 128.3, 127.7, 122.9, 118.4, 116.8, 113.9, 100.2, 89.2, 78.3, 57.0, 55.8, 53.7, 30.8, 29.5. HRMS (ESI-TOF⁺); m/z [M+H]⁺ calcd for C₃₁H₃₁FN₅O₂: 524.2462; found: 524.2457.

TBI-1003, 5-(4-Fluorophenyl)-(4-tetrahydropyranyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 9.08 (1H, s), 7.85 (1H, J=7.8, 1.5 Hz), 7.81 (1H, dd, J=5.1, 1.5 Hz), 7.72 (1H, dd, J=7.5, 1.8 Hz), 7.43 (2H, t, J=8.7 Hz), 7.33 (2H, dd, J=8.7, 4.8 Hz), 7.17 (2H, m), 6.97 (1H, s), 6.92 (1H, dd, J=7.8, 5.1 Hz), 6.48 (1H, dd, J=7.8, 1.2 Hz), 5.24 (1H, s), 4.04 (3H, s), 4.00 (2H, m), 3.50 (2H, m), 3.42 (1H, m), 1.69 (4H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8, 155.3, 151.2, 151.0, 142.6, 138.7, 135.7, 135.2, 133.4, 131.7, 130.8, 130.7, 128.3, 127.8, 124.9, 124.3, 123.0, 118.4, 116.8, 113.9, 100.3, 88.9, 65.6, 53.7, 53.3, 33.3. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₇FN₅O₂: 496.2149; found: 496.2145.

TBI-1004, 5-(4-Fluorophenyl)-3-(1-methylethyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 7.83 (m, 2H), 7.70 (dd, J=7.5, 1.5 Hz, 1H), 7.42 (t, J=8.7 Hz, 2H), 7.34 (dd, J=8.7, 4.8 Hz, 2H), 7.16 (m, 2H), 6.91 (m, 2H), 6.47 (d, J=7.2 Hz, 1H), 5.28 (s, 1H), 4.03 (s, 3H), 3.45 (m, 1H), 1.11 (d, J=6.6 Hz, 6H). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, J=248.9 Hz), 155.6, 151.1, 150.8, 142.9, 139.0, 135.7, 135.1, 133.5, 131.7, 130.9, 130.8, 128.2, 127.7, 125.3, 124.8, 123.0, 118.5 (d, J=23.1 Hz), 116.8, 113.9, 100.3, 89.3, 53.7, 49.3, 23.4. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₅FN₅O: 454.2043; found: 454.2042.

TBI-1005, 5-(4-Fluorophenyl)-3-(N-methyl-4-piperidyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 9.12 (s, 1H), 7.85 (dd, J=7.8, 1.5 Hz, 1H), 7.80 (dd, J=4.8, 1.5 Hz, 1H), 7.71 (dd, J=7.2, 1.5 Hz, 1H), 7.43 (t, 8.7 Hz, 2H), 7.33 (dd, J=8.7, 5.1 Hz, 2H), 7.16 (m, 2H), 6.97 (s, 1H), 6.92 (dd, J=7.8, 4.8 Hz, 1H), 6.48 (d, J=7.8 Hz, 1H), 5.24 (s, 1H), 4.04 (s, 3H), 3.21 (m, 1H), 2.75 (m, 2H), 2.31 (s, 3H), 2.14 (m, 2H), 1.70 (m, 4H). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, J=250 Hz), 155.3, 151.1, 151.0, 142.6, 138.6, 135.6, 135.2, 133.4, 131.8, 130.9, 130.8, 128.3, 127.7, 125.0, 124.1, 123.0, 118.4 (d, J=23.1 Hz), 116.8, 113.9, 100.2, 89.0, 53.7, 53.4, 46.5, 32.6. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₃₀FN₆O: 509.2465: found: 509.2466.

TBI-1008, 5-(4-Fluorophenyl)-3-(4-hydroxycyclohexyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 7.84 (d, J=7.8 Hz, 1H), 7.8 (d, J=5.1 Hz, 1H), 7.70 (dd, J=7.5, 1.5 Hz, 1H), 7.43 (t, J=8.7 Hz, 2H), 7.33 (dd, J=8.7, 5.1 Hz, 2H), 7.16 (m, 2H), 6.94 (s, 1H), 6.90 (dd, J=7.8, 5.1 Hz, 1H), 6.48 (d, J=7.5 Hz, 1H), 5.24 (s, 1H), 4.03 (s, 3H), 3.73 (m, 1H), 3.10 (m, 1H), 2.03 (m, 2H), 1.70 (m, 2H), 1.48 (m, 2H), 1.27 (m, 2H). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, J=249.3 Hz), 155.4, 151.4, 151.1, 142.8, 138.8, 135.6, 135.1, 133.4, 131.8, 130.9, 130.8, 128.3, 127.7, 124.8, 124.7, 122.9, 118.4 (d, J=22.7 Hz), 116.8, 113.9, 100.2, 89.2, 69.8, 56.8, 53.7, 33.4, 30.9. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₂₉FN₅O₂: 510.2305; found: 510.2304.

TBI-1009, 5-(4-Fluorophenyl)-3-cyclohexylimino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 9.04 (s, 1H), 7.84 (d, J=7.5 Hz, 1H), 7.80 (d, J=4.8 Hz, 1H), 7.69 (d, J=7.5 Hz, 1H), 7.42 (t, 8.4 Hz, 2H), 7.34 (dd, J=8.4, 4.8 Hz, 2H), 7.14 (m, 2H), 6.91 (m, 2H), 6.47 (d, J=8.1 Hz, 1H), 5.24 (s, 1H), 4.03 (s, 3H), 3.13 (m, 1H), 1.76 (m, 2H), 1.59 (m, 3H), 1.33 (m, 5H). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, J=248.9 Hz), 155.4, 151.4, 150.6, 142.9, 138.6, 135.6, 135.0, 133.5, 131.9, 130.9, 130.8, 128.2, 127.6, 125.0, 124.5, 122.8, 118.3 (d, J=22.6 Hz), 116.8, 113.8, 100.1, 89.4, 57.4, 53.7, 33.5, 26.0, 24.3. HRMS (ESI-TOF⁺): m/z calcd for C₃₀H₂₉FN₅O: 494.2356: found: 494.2358.

TBI-1010, 5-(4-Fluorophenyl)-3-cyclopropylimino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.58 (s, 1H), 7.81 (m, 2H), 7.66 (d, J=7.2 Hz, 1H), 7.37 (m, 4H), 7.13 (m, 2H), 6.90 (m, 2H), 6.42 (d, J=7.8 Hz, 1H), 5.52 (s, 1H), 3.99 (s, 3H), 2.73 (m, 1H), 0.88 (d, J=4.8 Hz, 2H), 0.82 (s, 2H). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, J=248.9 Hz), 155.4, 152.7, 151.5, 142.7, 138.9, 135.8, 134.9, 133.5, 132.0, 131.0, 130.9, 128.1, 127.6, 125.0, 124.8, 122.8, 118.5 (d, J=22.7 Hz), 116.8, 113.8, 100.1, 89.6, 53.7, 32.9, 10.0. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₃FN₅O: 452.1887: found: 452.1885.

TBI-1012, 5-(4-Fluorophenyl)-3-(4-tetrahydropyranyl)imino-2-(2-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.29 (d, J=4.5 Hz, 1H), 7.83 (d, J=8.1 Hz, 1H), 7.70 (d, J=7.8 Hz, 1H), 7.44 (t, J=8.1 Hz, 2H), 7.33 (dd, J=8.1, 4.8 Hz, 2H), 7.18 (m, 3H), 6.64 (s, 1H), 6.49 (d, J=7.2 Hz, 1H), 5.26 (s, 1H), 3.98 (m, 2H), 3.43 (m, 3H), 2.50 (s, 3H), 1.66 (m, 4H). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, J=249.7 Hz), 152.1, 151.1, 150.7, 144.2, 144.0, 135.6, 135.3, 134.6, 133.4, 131.5, 130.8, 130.7, 129.0, 128.3, 127.8, 123.1, 121.7, 118.5 (d, J=22.7 Hz), 114.0, 99.0, 88.8, 65.9, 53.7, 33.3, 20.9. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₇FN₅O: 480.2200; found: 480.2197.

TBI-1013, 5-(4-Fluorophenyl)-3-(4-methoxycyclohexyl)imino-2-(2-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.27 (d, J=4.2 Hz, 1H), 7.81 (d, J=8.1 Hz, I H), 7.68 (dd, J=7.5, 1.8 Hz, 1H), 7.42 (t, J=8.7 Hz, 2H), 7.33 (dd, J=8.7, 5.1 Hz, 2H), 7.16 (m, 3H), 6.60 (s, 1H), 6.49 (dd, J=7.2, 1.8 Hz, 1H), 5.26 (s, 1H), 3.36 (s, 3H), 3.22 (m, 1H), 3.11 (m, 1H), 2.54 (s, 3H), 2.06 (m, 2H), 1.72 (m, 2H), 1.42 (m, 2H), 1.21 (m, 2H). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, J=249.7 Hz), 152.0, 151.1, 150.9, 144.1, 144.0, 135.6, 135.1, 134.7, 133.4, 133.3, 131.6, 130.8, 130.7, 128.9, 128.2, 127.7, 123.0, 121.7, 118.4 (d, J=22.7 Hz), 113.9, 98.9, 89.0, 57.0, 55.8, 31.0, 29.7, 20.9. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₁FN₅O: 508.2513; found: 508.2516.

TBI-1014, 5-(4-Fluorophenyl)-3-cyclopropylimino-2-(2-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.28 (d, J=7.5 Hz, 1H), 7.78 (d, J=8.1 Hz, 1H), 7.65 (d, J=7.2 Hz, 1H), 7.38 (m, 4H), 7.14 (m, 3H), 6.49 (s, 1H), 6.43 (d, J=8.1 Hz, 1H), 5.54 (s, 1H), 2.76 (m, 1H), 2.51 (s, 3H), 0.90 (m, 2H), 0.80 (m, 2H). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, J=250.0 Hz), 152.6, 152.3, 151.2, 144.5, 144.1, 135.7, 135.0, 134.5, 133.5, 131.8, 131.0, 130.9, 129.8, 128.1, 127.6, 122.9, 121.7, 118.5 (d, J=22.6 Hz), 113.9, 98.9, 89.4, 32.8, 20.9, 10.1. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₃FN₅: 436.1937; found: 436.1939.

TBI-1015, 5-(4-Fluorophenyl)-(4-hydroxycyclohexyl)imino-2-(2-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.28 (d, J=4.8 Hz, 1H), 7.82 (d, J=8.1 Hz, 1H), 7.69 (d, J=7.5 Hz, 1H), 7.44 (t, J=8.1 Hz, 2H), 7.34 (dd, J=8.1, 4.5 Hz, 2H), 7.17 (m, 3H), 6.61 (s, 1H), 6.50 (d, J=7.8 Hz, 1H), 5.26 (s, 1H), 3.71 (m, 1H), 3.11 (m, 1H), 2.54 (s, 3H), 2.00 (m, 2H), 1.71 (m, 2H), 1.46 (m, 2H), 1.28 (m, 2H). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, J=249.3 Hz), 152.1, 151.2, 150.9, 144.2, 144.0, 135.6, 135.2, 134.7, 133.4, 131.6, 130.8, 130.7, 129.1, 128.3, 127.7, 123.0, 121.7, 118.4 (d, J=22.7 Hz), 114.0, 98.9, 89.0, 69.8, 56.9, 33.5, 31.1, 20.9. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₂₉FN₅O: 494.2356; found: 494.2357.

TBI-1016, 5-(4-Fluorophenyl)-3-cyclobutylimino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 7.83 (m, 2H), 7.70 (d, J=7.5 Hz, 1H), 7.42 (t, J=8.1 Hz, 2H), 7.32 (dd, J=8.1, 4.5 Hz, 2H), 7.16 (m, 2H), 6.91 (m, 2H), 6.47 (d, J=7.5 Hz, 1H), 5.07 (s, 1H), 4.04 (s, 3H), 3.88 (m, 1H), 2.18 (n), 2H), 2.06 (m, 2H), 1.75 (m, 2H). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, J=249.3 Hz), 155.4, 151.5, 151.2, 142.7, 138.8, 135.7, 134.6, 133.4, 131.7, 131.0, 130.9, 128.3, 127.7, 124.8, 123.0, 118.4 (d, J=22.7 Hz), 116.8, 113.9, 100.3, 90.8, 54.9, 53.7, 32.0, 16.0. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₅FN₅O: 466.2043; found: 466.2042.

TBI-1017, 5-(4-Fluorophenyl)-3-cyclobutylimino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.46 (s, 1H), 7.69 (m, 2H), 7.43 (t, J=8.4 Hz, 2H), 7.34 (dd, J=8.4, 5.1 Hz, 2H), 7.16 (m, 3H), 6.72 (s, 1H), 6.49 (d, J=8.4 Hz, 1H), 5.09 (s, 1H), 3.86 (m, 1H), 2.57 (s, 3H), 2.17 (m, 2H), 2.05 (m, 2H), 1.74 (m, 2H). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, J=249.3 Hz), 153.5, 151.3, 150.9, 144.3, 143.8, 135.7, 134.7, 133.9, 133.5, 131.5, 130.9, 130.8, 129.5, 128.3, 127.7, 123.1 (d, J=16.5 Hz), 118.4 (d, J=22.7 Hz), 113.9, 98.9, 90.6, 54.8, 32.0, 23.8, 16.0. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₅FN₅: 450.2094; found: 450.2092.

TBI-1018, 5-(4-Fluorophenyl)-3-cyclobutylimino-2-(2-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.30 (d, J=4.8 Hz, 1H), 7.80 (d, J=7.5 Hz, 1H), 7.68 (d, J=7.5 Hz, 1H), 7.44 (t, J=8.4 Hz, 2H), 7.34 (dd, J=8.4, 4.8 Hz, 2H), 7.17 (m, 3H), 6.55 (s, 1H), 6.49 (d, J=7.8 Hz, 1H), 5.10 (s, 1H), 3.91 (m, 1H), 2.57 (s, 3H), 2.18 (m, 2H), 2.04 (m, 2H), 1.78 (m, 2H). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, J=248.9 Hz), 152.5, 151.2, 150.9, 144.4, 144.2, 135.7, 134.7, 134.6, 133.5, 131.5, 130.9, 130.8, 129.6, 128.2, 127.7, 123.0, 121.7, 118.4 (d, J=22.7 Hz), 114.0, 99.0, 90.5, 54.8, 32.0, 21.0, 16.0. HRMS (ESI-TOF⁺): [M+H]⁺ calcd for C₂₈H₂₅FN₅: 450.2094: found: 450.2096.

TBI-1019, 5-(3-Trifluoromethoxyphenyl)-3-(1-methylethyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.59 (d, J=2.1 Hz, 1H), 8.34 (d, J=4.5 Hz, 1H), 7.8 (t, J=8.4 Hz, 2H), 7.70 (d, J=7.2 Hz, 1H), 7.53 (d, J=8.7 Hz, 1H), 7.30 (m, 3H), 7.17 (m, 2H), 6.83 (s, 1H), 6.46 (d, J=8.1 Hz, 1H), 5.25 (s, 1H), 3.43 (m, 1H), 1.10 (d, J=7.8 Hz, 3H), 1.07 (d, J=7.8 Hz, 3H). ¹³C NMR (100 MHz, CDCl₃) δ: 151.2, 151.0, 150.3, 144.3, 144.0, 143.7, 138.9, 136.8, 135.6, 134.7, 132.7, 131.2, 128.4, 128.0, 127.8, 127.6, 123.6, 123.1, 122.4. 122.0, 118.0 (q, J=249.3 Hz), 113.7, 99.4, 89.1, 49.5, 23.7, 23.2. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₃F₃N₅O: 490.1855; found: 490.1855.

TBI-1020, 5-(3-Trifluoromethoxyphenyl)-3-(4-tetrahydropyranyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.61 (s, 1H), 8.36 (d, J=4.5 Hz, 1H), 7.80 (m, 2H), 7.73 (d, J=7.8 Hz, 1H), 7.56 (d, J=7.8 Hz, 1H), 7.30 (m, 3H), 7.20 (m, 2H), 6.87 (s, 1H), 6.50 (d, J=7.5 Hz, 1H), 5.22 (s, 1H), 3.97 (m, 2H), 3.34 (m, 3H), 1.65 (m, 4H). ¹³C NMR (100 MHz, CDCl₃) δ: 151.1, 150.7, 144.5, 144.0, 143.6, 138.8, 136.6, 135.6, 134.8, 132.7, 131.0, 128.5, 128.1, 128.0, 127.6, 123.7, 123.3, 122.6, 122.1, 119.0 (q, J=249.3 Hz), 113.8, 99.6, 89.0, 66.2, 54.7, 33.6, 33.2. HRMS (ESI-TOP): m/z [M+H]⁺ calcd for C₂₉H₂₅F₃N₅O₂: 532.1960; found: 532.1958.

TBI-1021, 5-(3-Trifluoromethoxyphenyl)-3-cyclopropylimino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.59 (d, J=2.7 Hz, 1H), 8.48 (s, 1H), 8.31-4.5 Hz, 1H), 7.95 (t, J=8.1 Hz, 1H), 7.84 (d, J=8.1 Hz, 1H), 7.75 (m, 2H), 7.64 (d, J=7.4 Hz, 2H), 7.44 (dd, J=8.1, 4.5 Hz, 1H), 7.21 (m, 2H), 6.61 (s, 1H), 6.42 (d, J=7.8 Hz, 1H), 5.44 (s, 1H), 2.65 (m, 1H), 0.83 (d, J=6.3 Hz, 2H), 0.76 (s, 2H). ¹³C NMR (100 MHz, CDCl₃) δ: 152.0, 150.4, 150.1, 144.1, 144.0, 143.4, 138.4, 136.6, 135.3, 134.2, 133.4, 131.2, 128.5, 128.4, 128.1, 127.8, 123.9, 122.7, 122.3, 119.0 (q, J=249.3 Hz), 113.7, 98.8, 88.7, 32.6, 9.6. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₁F₃N₅O: 488.1698; found: 488.1697.

TBI-1022, 5-(3-Trifluoromethoxyphenyl)-3-cyclohexylimino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.58 (d, J=2.6 Hz, 1H), 8.33 (dd, J=4.8, 1.2 Hz, 1H), 7.80 (m, 2H), 7.69 (dd, J=7.8, 1.8 Hz, 1H), 7.54 (d, J=7.2 Hz, 1H), 7.30 (m, 4H), 7.17 (m, 2H), 6.79 (s, 1H), 6.48 (dd, J=7.2, 2.1 Hz, 1H), 5.23 (s, 1H), 3.06 (m, 1H), 1.73 (m, 2H), 1.58 (m, 3H), 1.38 (m, 2H), 1.20 (m, 3H). ¹³C NMR (100 MHz, CDCl₃) δ: 151.1, 151.0, 150.4, 144.3, 143.9, 143.7, 138.9, 136.8, 135.6, 134.6, 132.6, 131.2, 128.4, 127.9, 127.8, 127.6, 123.6, 123.1, 122.4, 122.1, 120.0 (q, J=249.3 Hz), 113.7, 99.4, 89.4, 58.1, 33.8, 33.4, 25.8, 24.7, 24.6. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₂₇F₃N₅O: 530.2168; found: 530.2170.

TBI-1023, 5-(4-Fluorophenyl)-3-cyclohexylimino-2-(2-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.26 (dd, J=4.5, 1.2 Hz, 1H), 7.82 (dd, J=8.4, 1.2 Hz, 1H), 7.67 (dd, J=7.5, 2.0 Hz, 1H), 7.43 (t, J=8.4 Hz, 2H), 7.34 (dd, J=8.7, 5.1 Hz, 2H), 7.15 (m, 3H), 6.61 (s, 1H), 6.48 (dd, J=7.8, 1.5 Hz, 1H), 5.26 (s, 1H), 3.13 (m, 1H), 2.55 (s, 3H), 1.74 (m, 2H), 1.62 (m, 3H), 1.39 (m, 2H), 1.26 (m, 3H). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, J=248.9 Hz), 152.0, 151.1, 150.5, 144.0, 135.6, 135.1, 134.8, 133.5, 131.7, 130.9, 130.8, 128.8, 128.2, 127.6, 122.9, 121.7, 118.4 (d, J=22.7 Hz), 113.9, 98.8, 89.2, 57.4, 33.6, 25.9, 24.4, 20.9. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₂₉FN₅: 478.2407; found: 478.2408.

TBI-1024, 5-(3-Trifluoromethoxyphenyl)-3-(4-methoxycyclohexyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.58 (d, J=2.4 Hz, 1H), 8.34 (d, J=4.8 Hz, 1H), 780 (t, J=8.1 Hz, 2H), 7.72 (dd, J=7.2, 2.1 Hz, 1H), 7.53 (dd, J=8.4, 0.6 Hz, 1H), 7.31 (m, 2H), 7.27 (m, 1H), 7.19 (m, 2H), 6.84 (s, 1H), 6.50 (dd, J=7.5, 1.8 Hz, 1H), 5.20 (s, 1H), 3.36 (s, 3H), 3.18 (m, 1H), 3.05 (m, 1H), 2.07 (m, 2H), 1.66 (m, 2H), 1.44 (m, 2H), 1.16 (m, 2H). ¹³C NMR (100 MHz, CDCl₃) δ: 151.2, 151.1, 150.8, 144.4, 144.0, 143.6, 138.7, 136.7, 135.6, 134.8, 132.7, 131.1, 128.5, 128.0, 127.5, 123.7, 123.2, 122.5, 121.9, 119.0 (q, J=249.3 Hz), 113.8, 99.5, 89.2, 57.5, 55.8, 31.4, 30.9, 30.1, 29.9. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₂₉F₃N₅O₂: 560.2273; found: 560.2274.

TBI-1025, 5-(4-Fluorophenyl)-3-(1-methylethyl)imino-2-(5-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.40 (s, 1H), 8.17 (s, 1H), 7.69 (d, J=7.5 Hz, 1H), 7.58 (s, 1H), 7.42 (t, J=8.4 Hz, 2H), 7.34 (m, 2H), 7.16 (m, 2H), 6.83 (s, 1H), 6.46 (d, J=7.8 Hz, 1H), 5.27 (s, 1H), 3.45 (m, 1H), 2.38 (s, 3H), 1.10 (s, 3H), 1.08 (s, 3H). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, J=249.3 Hz), 151.0, 150.4, 144.9, 143.7, 141.1, 136.4, 135.6, 135.1, 133.5, 131.7, 130.9, 130.8, 128.4, 128.2, 127.7, 122.9, 118.5 (d, J=22.7 Hz), 113.9, 99.3, 89.1, 49.4, 23.5, 18.4. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₅FN₅: 438.2094; found: 438.2095.

TBI-1026, 5-(4-Fluorophenyl)-3-(4-methoxycyclohexyl)imino-2-(5-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.39 (d, J=2.4 Hz, 1H), 8.17 (s, 1H), 7.70 (dd, J=7.5, 1.5 Hz, 1H), 7.58 (s, 1H), 7.42 (t, J=8.4 Hz, 2H), 7.33 (dd, J=8.7, 5.1 Hz, 2H), 7.17 (m, 2H), 6.83 (s, 1H), 6.50 (dd, J=7.5, 1.8 Hz, 1H), 5.25 (s, 1H), 3.36 (s, 3H), 3.20 (m, 1H), 3.08 (m, 1H), 2.38 (s, 3H), 2.07 (m, 2H), 1.68 (m, 2H), 1.42 (m, 2H), 1.18 (m, 2H). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, J=249.4 Hz), 151.1, 150.9, 144.9, 143.6, 141.1, 136.3, 135.6, 135.1, 133.5, 133.3, 131.6, 130.8, 130.7, 128.3, 128.2, 127.8, 123.0, 118.4 (d, J=22.7 Hz), 114.0, 99.4, 89.1, 78.4, 57.4, 55.8, 31.1, 29.9, 18.5. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₁FN₅O: 508.2513; found: 508.2516.

TBI-1027, 5-(3-Trifluoromethoxyphenyl)-3-cyclobutylimino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.60 (d, J=2.4 Hz, 1H), 8.34 (d, J=4.8 Hz, 1H), 7.80 (m, 2H), 7.71 (d, J=7.2 Hz, 1H), 7.54 (d, J=8.4 Hz, 1H), 7.31 (m, 3H), 7.18 (m, 2H), 6.83 (s, 1H), 6.48 (d, J=8.1 Hz, 1H), 5.07 (s, 1H), 3.87 (m, 1H), 2.14 (m, 2H), 2.04 (m, 2H), 1.72 (m, 2H). ¹³C NMR (100 MHz, CDCl₃) δ: 151.1, 150.9, 144.4, 144.0, 143.6, 138.8, 136.6, 135.6, 134.3, 132.6, 131.1, 128.4, 128.1, 128.0, 127.6, 123.7, 123.2, 122.4, 122.0, 119.0 (q, J=249.3 Hz), 113.8, 99.5, 90.6, 54.9, 32.0, 31.8, 16.0. HRMS (ESI-TOF⁺): [M+H]⁺ calcd for C₂₈H₂₃F₃N₅O: 502.1855; found: 502.1858.

TBI-1028, 5-(4-Fluorophenyl)-3-(4-tetrahydropyranyl)imino-2-(5-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.30 (d, J=2.1 Hz, 1H), 8.07 (s, 1H), 7.60 (dd, J=7.2, 1.8 Hz, 1H), 7.46 (s, 1H), 7.32 (t, J=8.4 Hz, 2H), 7.23 (dd, J=8.7, 5.1 Hz, 2H), 7.07 (m, 2H), 6.75 (s, 1H), 6.38 (dd, J=7.5, 1.5 Hz, 1H), 5.14 (s, 1H), 3.86 (m, 2H), 3.29 (m, 3H), 2.27 (s, 3H), 1.54 (m, 4H). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, J=249.7 Hz), 151.1, 150.8, 145.1, 143.7, 141.1, 136.3, 135.6, 135.2, 133.6, 133.4, 131.5, 130.8, 130.7, 128.5, 128.3, 127.9, 123.1, 118.4 (d, J=22.7 Hz), 114.0, 99.5, 88.9, 66.1, 54.3, 33.4, 18.4. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₇FN₅O: 480.2200; found: 4807201.

TBI-1029, 5-(4-Fluorophenyl)-3-cyclohexylimino-2-(5-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.39 (s, 1H), 8.16 (s, 1H), 7.69 (d, J=7.2 Hz, 1H), 7.58 (s, 1H), 7.43 (t, J=7.5 Hz, 2H), 7.34 (m, 2H), 7.16 (m, 2H), 6.82 (s, 1H), 6.48 (d, J=7.8 Hz, 1H), 5.25 (s, 1H), 3.08 (m, 1H), 2.38 (s, 3H), 1.75 (m, 2H), 1.60 (m, 3H), 1.38 (m, 2H), 1.22 (m, 3H). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, J=249.4 Hz), 151.1, 150.5, 144.9, 143.8, 141.1, 136.5, 135.7, 135.0, 133.5, 131.7, 130.9, 130.8, 128.3, 128.2, 127.6, 122.9, 118.4 (d, J=22.9 Hz), 113.9, 99.3, 89.3, 57.9, 33.6, 25.8, 24.6, 18.5. HRMS (ESI-TOF⁺): [M+H]⁺ calcd for C₃₀H₂₉FN₅: 478.2407; found: 478.2405.

TBI-1030, 5-(4-Fluorophenyl)-3-cyclopropylimino-2-(5-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.35 (d, J=1.5 Hz, 1H), 8.16 (s, 1H), 7.67 (dd, J=7.2, 1.5 Hz, 1H), 7.55 (s, 1H), 7.38 (m, 4H), 7.15 (m, 2H), 6.78 (s, 1H), 6.44 (d, J=7.3 Hz, 1H), 5.53 (s, 1H), 2.74 (m, 1H), 2.37 (s, 3H), 0.87 (m, 2H), 0.81 (m, 2H). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, J=248.9 Hz), 152.4, 151.3, 145.0, 143.5, 141.2, 136.2, 135.7, 134.9, 133.5, 131.9, 131.0, 130.9, 128.5, 128.1, 127.6, 122.9, 118.5 (d, J=22.4 Hz), 113.8, 99.3, 89.4, 32.8, 18.4, 9.9. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₃FN₅: 436.1937; found: 436.1940.

TBI-1031, 5-(4-Fluorophenyl)-3-cyclobutylimino-2-(5-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.41 (d, J=2.1 Hz, 1H), 8.18 (s, 1H), 7.72 (dd, J=7.8, 1.2 Hz, 1H), 7.58 (s, 1H), 7.43 (t, J=8.4 Hz, 2H), 7.33 (dd, 8.7, 5.1 Hz, 2H), 7.17 (m, 2H), 6.83 (s, 1H), 6.49 (dd, J=7.5, 1.5 Hz, 1H), 5.08 (s, 1H), 3.86 (m, 1H), 2.38 (s, 3H), 2.16 (m, 2H), 2.04 (m, 2H), 1.75 (m, 2H). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, J=248.9 Hz), 151.2, 151.0, 145.1, 143.7, 141.2, 136.3, 135.7, 134.7, 133.5, 131.6, 130.9, 130.8, 128.5, 128.3, 127.8, 123.1, 118.4 (d, J=22.9 Hz), 114.0, 99.4, 90.6, 54.8, 32.0, 18.5, 16.0. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₅FN₅: 450.2094; found: 450.2092.

TBI-1032, 5-(3-Trifluoromethoxyphenyl)-3-(1-methylethyl)imino-2-(2-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.28 (dd, J=5.4, 1.8 Hz, 1H), 7.80 (t, J=8.1 Hz, 2H), 7.68 (dd, J=7.5, 1.8 Hz, 1H), 7.53 (d, J=8.1 Hz, 1H), 7.30 (d, J=7.8 Hz, 1H), 7.28 (m, 1H), 7.17 (m, 3H), 6.57 (s, 1H), 6.46 (dd, J=7.8, 1.5 Hz, 1H), 5.26 (s, 1H), 3.45 (m, 1H), 2.55 (s, 3H), 1.10 (d, J=6.6 Hz, 3H), 1.07 (d, J=6.3 Hz, 3H). ¹³C NMR (100 MHz, CDCl₃) δ: 152.4, 151.2, 151.0, 150.3, 144.3, 144.2, 139.0, 135.5, 134.7, 132.7, 131.2, 129.3, 128.3, 127.7, 127.6, 123.1, 122.4, 122.0, 121.7, 119.0 (q, J=249.3 Hz), 113.7, 98.8, 89.1, 49.4, 23.7, 23.2, 20.9. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₅F₃N₅O: 504.2011; found: 504.2009.

TBI-1033, 5-(3-Trifluoromethoxyphenyl)-3-(4-methoxycyclohexyl)imino-2-(2-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.28 (dd, J=5.4, 1.8 Hz, 1H), 7.80 (t, J=8.1 Hz, 2H), 7.68 (dd, J=7.2, 2.1 Hz, 1H), 7.53 (d, J=8.1 Hz, 1H), 7.33 (d, J=7.8 Hz, 1H), 7.26 (m, 1H), 7.18 (m, 3H), 6.59 (s, 1H), 6.50 (dd, J=7.8, 1.5 Hz, 1H), 5.21 (s, 1H), 3.36 (s, 3H), 3.20 (m, 1H), 3.08 (m, 1H), 2.54 (s, 3H), 2.06 (m, 2H), 1.70 (m, 2H), 1.40 (m, 2H), 1.19 (m, 2H). ¹³C NMR (100 MHz, CDCl₃) δ: 152.2, 151.2, 151.1, 150.9, 144.3, 144.0, 138.8, 135.5, 134.7, 134.6, 132.7, 131.1, 129.2, 128.3, 127.8, 127.5, 123.2, 122.5, 121.9, 121.7, 119.0 (q, J=249.3 Hz), 113.7, 98.9, 89.1, 78.4, 57.2, 55.8, 31.3, 30.8, 29.8, 29.7, 20.9. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₂H₃₁F₃N₅O₂: 574.2430; found: 574.2430.

TBI-1034, 5-(3-Trifluoromethoxyphenyl)-3-cyclohexylimino-2-(2-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.28 (dd, J=5.4, 1.8 Hz, 1H), 7.80 (t, J=8.1 Hz, 2H), 7.68 (dd, J=7.2, 1.8 Hz, 1H), 7.53 (d, J=8.7 Hz, 1H), 7.33 (d, J=9.0 Hz, 1H), 7.29 (m, 1H), 7.16 (m, 3H), 6.59 (s, 1H), 6.48 (dd, J=7.5, 1.8 Hz, 1H), 5.23 (s, 1H), 3.09 (m, 1H), 2.55 (s, 3H), 1.73 (m, 1H), 1.58 (m, 3H), 1.36 (m, 2H), 1.22 (m, 3H). ¹³C NMR (100 MHz, CDCl₃) δ: 152.1, 151.1, 151.0, 150.0, 144.1, 138.9, 135.5, 134.7, 134.6, 132.6, 131.1, 128.9, 128.3, 127.6, 123.0, 122.4, 122.1, 121.6, 119.0 (q, J=249.3 Hz), 113.6, 98.8, 89.3, 57.7, 33.8, 33.4, 25.8, 24.4, 20.9. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₂₉F₃N₅O: 544.2324; found: 544.2324.

TBI-1035, 5-(3-Trifluoromethoxyphenyl)-3-(4-tetrahydropyranyl)imino-2-(2-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.30 (dd, J=4.8, 1.2 Hz, 1H), 7.82 (t, J=7.5 Hz, 2H), 7.71 (dd, J=7.5, 1.8 Hz, 1H), 7.56 (d, J=8.1 Hz, 1H), 7.33 (d, J=7.8 Hz, 1H), 7.29 (m, 1H), 7.19 (m, 3H), 6.62 (s, 1H), 6.50 (dd, J=7.8, 1.5 Hz, 1H), 5.23 (s, 1H), 3.96 (m, 2H), 3.42 (m, 3H), 2.56 (s, 3H), 1.64 (m, 4H). ¹³C NMR (100 MHz, CDCl₃) δ: 152.2, 151.0, 150.7, 144.3, 144.0, 138.8, 135.6, 134.8, 134.5, 132.7, 131.0, 129.2, 128.4, 127.9, 127.6, 123.3, 122.6, 122.1, 121.7, 119.0 (q, J=249.3 Hz), 113.8, 99.0, 88.9, 66.0, 54.1, 33.5, 33.1, 20.9. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₂₇F₃N₅O₂: 546.2117: found: 546.2119.

TBI-1038, 5-(3-Trifluoromethoxyphenyl)-3-(1-methylethyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 7.82 (m, 3H), 7.70 (dd, J=7.8, 1.8 Hz, 1H), 7.52 (d, J=8.7 Hz, 1H), 7.32 (d, J=7.8 Hz, 1H), 7.28 (brs, 1H), 7.16 (m, 2H), 6.90 (m, 2H), 6.45 (dd, J=7.2, 1.8 Hz, 1H), 5.24 (s, 1H), 4.04 (s, 3H), 3.42 (m, 1H), 1.11 (d, J=6.3 Hz, 3H), 1.08 (d, J=6.3 Hz, 3H). ¹³C NMR (100 MHz, CDCl₃) δ: 155.5, 151.2, 151.1, 150.6, 142.9, 138.9, 135.5, 134.6, 132.6, 131.3, 128.3, 127.7, 127.6, 125.0, 124.8, 123.0, 122.3, 122.0, 120.0 (q, J=249.3 Hz), 116.8, 113.6, 100.1, 89.3, 53.7, 49.4, 23.7, 23.2. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₅F₃N₅O₂: 520.1960; found: 520.1959.

TBI-1039, 5-(3-Trifluoromethoxyphenyl)-3-(4-methoxycyclohexyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.90 (brs, 1H), 7.82 (m, 3H), 7.71 (dd, J=6.9, 2.1 Hz, 1H), 7.53 (d, J=7.8 Hz, 1H), 7.33 (d, J=7.8 Hz, 1H), 7.26 (brs, 1H), 7.17 (m, 2H), 6.92 (m, 2H), 6.49 (dd, J=7.5, 1.5 Hz, 1H), 5.20 (s, 1H), 4.03 (s, 3H), 3.36 (s, 3H), 3.22 (m, 1H), 3.08 (m, 1H), 2.05 (m, 2H), 1.70 (m, 2H), 1.44 (m, 2H), 1.18 (m, 2H). ¹³C NMR (100 MHz, CDCl₃) δ: 155.4, 151.2, 151.1, 142.8, 138.8, 135.6, 134.7, 132.6, 131.2, 128.3, 127.8, 127.6, 124.8, 123.1, 122.4, 122.0, 119.0 (q, J=249.3 Hz), 116.8, 113.7, 100.2, 89.3, 78.4, 57.1, 55.8, 53.7, 31.1, 30.6, 29.7, 29.5. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₂H₃₁F₃N₅O₃: 590.2379; found: 590.2378.

TBI-1040, 5-(3-Trifluoromethoxyphenyl)-3-cyclohexylimino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 9.00 (brs, 1H), 7.80 (m, 3H), 7.69 (dd, J=7.5, 1.8 Hz, 1H), 7.53 (d, J=8.7 Hz, 1H), 7.33 (d, J=7.8 Hz, 1H), 7.28 (brs, 1H), 7.16 (m, 2H), 6.92 (m, 2H), 6.46 (dd, J=7.8, 1.5 Hz, 1H), 5.22 (s, 1H), 4.03 (s, 3H), 3.09 (m, 1H), 1.74 (m, 2H), 1.58 (m, 3H), 1.37 (m, 2H), 1.22 (m, 3H). ¹³C NMR (100 MHz, CDCl₃) δ: 155.4, 151.3, 151.1, 150.5, 142.9, 138.9, 138.7, 135.6, 134.6, 132.6, 131.3, 128.3, 127.7, 124.9, 124.6, 123.0, 122.3, 122.2, 120.0 (q, J=249.3 Hz), 116.8, 113.6, 100.1, 89.5, 57.6, 53.7, 33.7, 33.3, 25.9, 24.3. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₂₉F₃N₅O₂: 560.2273; found: 560.2272.

TBI-1041, 5-(3-Trifluoromethoxyphenyl)-3-(4-tetrahydropyranyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 7.82 (m, 3H), 7.72 (d, J=7.2 Hz, 1H), 7.55 (d, J=8.1 Hz, 1H), 7.33 (d, J=8.1 Hz, 1H), 7.29 (brs, 1H), 7.18 (m, 2H), 6.93 (m, 2H), 6.48 (d, J=7.8 Hz, 1H), 5.21 (s, 1H), 4.04 (s, 3H), 3.99 (m, 2H), 3.41 (m, 3H), 1.66 (m, 4H). ¹³C NMR (100 MHz, CDCl₃) δ: 155.3, 151.1, 150.9, 142.6, 138.8, 135.6, 134.8, 132.7, 131.1, 128.4, 127.9, 127.6, 124.7, 124.5, 123.2, 122.5, 122.1, 119.0 (q, J=249.3 Hz), 116.8, 113.7, 100.3, 89.0, 65.7, 53.7, 33.4, 33.0. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₂₇F₃N₅O₃: 562.2066; found: 562.2065.

TBI-1042, 5-(4-Fluorophenyl)-3-(4-tetrahydrothiopyranyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 9.11 (1H, s), 7.85 (1H, dd, J=7.5, 1.5 Hz), 7.81 (1H, dd, J=5.1, 1.5 Hz), 7.72 (1H, dd, J=7.5, 1.8 Hz), 7.43 (2H, t, J=8.7 Hz), 7.33 (2H, dd, J=9.0, 5.1 Hz), 7.17 (2H, m), 6.98 (1H, s), 6.92 (1H, dd, J=7.8, 5.1 Hz), 6.49 (1H, dd 7.8, 1.2 Hz), 5.19 (1H, s), 4.06 (3H, s), 3.28 (1H, m), 2.95 (2H, m), 2.48 (2H, m), 1.86 (4H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, J=249.4 Hz), 155.3, 151.0, 150.8, 142.6, 138.7, 135.7, 135.3, 133.4, 131.7, 130.8, 130.7, 128.3, 127.8, 124.9, 124.2, 123.1, 118.5 (d, J=22.7 Hz), 116.8, 114.0, 100.3, 88.9, 55.1, 53.8, 34.0, 25.7. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₇FN₅OS: 512.1920: found: 512.1917.

TBI-1043, 5-(4-Fluorophenyl)-3-(4-tetrahydrothiopyranyl)imino-2-ethyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.29 (1H, d, J=4.5), 7.83 (1H, d, J=8.1 Hz), 7.70 (1H, d, J=7.5 Hz), 7.44 (2H, t, J=8.4 Hz), 7.34 (2H, dd, J=8.4, 4.8 Hz), 7.18 (3H, m), 6.63 (1H, s), 6.50 (1H, d, J=7.5 Hz), 5.21 (1H, s), 3.23 (1H, m), 2.83 (2H, m), 2.56 (3H, s), 2.50 (2H, m), 1.92 (2H, m), 1.81 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, J=249.4 Hz), 152.1, 150.8, 150.7, 144.3, 144.0, 135.7, 135.3, 134.6, 133.4, 131.5, 130.8, 130.7, 129.0, 128.3, 127.8, 123.1, 121.7, 118.5 (d, J=22.7 Hz), 114.0, 99.0, 88.8, 55.7, 34.2, 26.3, 20.9.

TBI-1044, 5-(2-Trifluoromethoxyphenyl)-3-(4-methoxycyclohexyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.90 (1H, hrs), 7.85 (1H, d, J=7.8 Hz), 7.81 (1H, dd, J=4.8, 0.9 Hz), 7.71 (2H, m), 7.62 (2H, m), 7.42 (1H, d, J=7.5 Hz), 7.17 (2H, m), 6.92 (2H, m), 6.45 (1H, d, J=7.5 Hz), 5.20 (1H, s), 4.03 (3H, s), 3.36 (3H, s), 3.23 (1H, m), 3.08 (1H, m), 2.05 (2H, m), 1.70 (2H, m), 1.44 (2H, m), 1.18 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 155.4, 152.1, 151.5, 146.2, 142.7, 138.8, 135.6, 134.0, 131.6, 131.3, 130.9, 128.7, 128.3, 127.8, 124.8, 121.5, 116.8, 113.5, 100.3, 89.2, 78.4, 57.2, 55.8, 53.7, 31.0, 30.6, 29.7, 29.6.

TBI-1045, 5-(2-Trifluoromethoxyphenyl)-3-(4-tetrahydropyranyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 9.04 (1H, s), 7.86 (1H, dd, J=7.8, 1.5 Hz), 7.82 (1H, dd, J=5.1, 1.5 Hz), 7.73 (2H, m), 7.64 (2H, m), 7.43 (1H, dd, J=7.8, 1.2 Hz), 7.19 (2H, m), 6.98 (1H, s), 6.93 (1H, dd, J=7.8, 5.1 Hz), 6.44 (1H, d, J=7.5 Hz), 5.21 (1H, s), 4.04 (3H, s), 4.00 (2H, m), 3.47 (3H, m), 1.65 (4H, m). ¹³C NMR (100 MHz, CDCl₃) 155.3, 151.3, 151.0, 146.2, 142.6, 138.8, 135.6, 134.2, 131.6, 131.3, 130.8, 128.8, 128.4, 127.9, 124.8, 124.5, 123.2, 121.6, 116.8, 113.5, 100.4, 88.9, 65.7, 65.6, 53.8, 53.5, 33.4, 33.1.

TBI-1046 5-(2-Trifluoromethoxyphenyl)-3-(1-methylethyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.88 (brs, I D), 7.83 (m, 2H), 7.69 (m, 4H), 7.43 (d, J=6.9 Hz, 1H), 7.16 (m, 2H), 6.92 (m, 2H), 6.40 (d, J=7.2 Hz, 1H), 5.24 (s, 1H), 4.04 (s, 3H), 3.45 (m, 1H), 1.11 (d, J=6.3 Hz, 3H), 1.10 (d, J=6.3 Hz, 3H). ¹³C NMR (100 MHz, CDCl₃) δ: 155.5, 151.3, 150.7, 146.3, 142.9, 138.8, 135.5, 134.0, 131.5, 131.4, 131.0, 128.9, 128.8, 128.2, 127.7, 125.0, 124.8, 123.0, 121.7, 116.8, 113.4, 100.2, 89.2, 53.7, 49.4, 23.6, 23.3.

TBI-1047, 5-(2-Trifluoromethoxyphenyl)-3-cyclohexylimino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 9.00 (br s, 1H), 7.85 (dd, J=8.1, 1.5 Hz, 1H), 7.80 (dd, J=4.2, 1.5 Hz, 1H), 7.67 (m, 4H), 7.43 (dd, J=7.8, 1.2 Hz, 1H), 7.16 (m, 2H), 6.93 (m, 2H), 6.43 (dd, J=7.5, 1.5 Hz, 1H), 5.21 (s, 1H), 4.03 (s, 3H), 3.10 (m, 1H), 1.76 (m, 2H), 1.58 (m, 3H), 1.41 (m, 2H), 1.22 (m, 3H). ¹³C NMR (100 MHz, CDCl₃) δ: 155.4, 151.4, 150.7, 146.3, 142.8, 138.7, 135.6, 133.9, 131.4, 131.0, 128.9, 128.7, 128.2, 127.7, 124.9, 124.7, 123.0, 121.5, 116.8, 113.4, 100.2, 89.4, 57.6, 53.7, 33.6, 33.3, 25.9, 24.3.

TBI-1048, 5-(4-Fluorophenyl)-3-(1,3-dimethoxyisopropyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.90 (brs, 1H), 7.83 (m, 2H), 7.72 (d, J=6.6 Hz, 1H), 7.36 (m, 4H), 7.17 (m, 2H), 6.92 (m, 2H), 6.48 (d, J=7.5 Hz, 1H), 5.47 (s, 1H), 4.02 (s, 3H), 3.70 (m, 1H), 3.55 (m, 2H), 3.39 (m, 2H), 3.28 (s, 6H). ¹³C NMR (100 MHz, CDCl₃) δ: 162.9 (d, J=250.0 Hz), 155.4, 153.5, 151.0, 142.7, 138.9, 135.7, 135.0, 133.4, 131.8, 130.9, 128.3, 127.8, 125.0, 123.0, 118.4 (d, J=23.1 Hz), 116.8, 114.0, 100.2, 90.2, 74.4, 59.1, 58.7, 53.7

TBI-1049, 5-(4-Fluorophenyl)-3-(2,3-dimethoxy-1-propyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 9.34 (brs, 1H), 8.78 (s, 1H), 8.13 (m, 2H), 7.89 (d, J=7.2 Hz, 1H), 7.63 (m, 4H), 7.46 (m, 2H), 6.99 (m, 2H), 6.83 (s, 1H), 6.14 (s, 1H), 3.96 (s, 3H), 3.59 m, 2H), 3.49 (m, 1H), 3.37 (m, 3H), 3.34 (s, 3H). ¹³C NMR (100 MHz, CDCl₃) δ: 163.6 (d, J=250.0 Hz), 157.8, 153.2, 144.1, 141.0, 138.7, 135.2, 134.4, 131.8, 130.3, 129.9, 129.6, 129.5, 127.3, 122.0, 118.9 (d, J=23.1 Hz), 117.3, 116.3, 107.0, 90.4, 78.2, 71.4, 59.5, 57.8, 53.7, 45.4,

TBI-1050, 5-(4-Chlorophenyl)-3-(1-methylethyl)imino-2-(3-nitro-2-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 12.24 (s, 1H), 8.72 (s, 1H), 8.66 (d, J=3.0 Hz, 1H), 8.56 (dd, J=8.4, 1.8 Hz, 1 Hz), 7.45 (m, 3H), 7.32 (m, 2H), 7.17 (m, 1H), 6.95 (dd, J=8.1, 4.5 Hz, 1H), 6.42 (m, 1H), 5.29 (s, 1H), 3.47 (m, 1H), 1.15 (d, J=6.3 Hz, 6H). ¹³C NMR (100 MHz, CDCl₃) δ: 154.3, 151.9, 150.5, 148.7, 140.4, 135.8, 135.7, 135.6, 135.2, 135.1, 132.2, 131.8, 130.8, 130.4, 129.0, 128.8, 122.9, 114.8, 113.8, 111.5, 89.1, 49.5, 23.5.

TBI-90B, 5-(4-Fluorophenyl)-3-(4-tetrahydrothiopyranyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.55 (1H, s), 8.17 (1H, d, J=4.8 Hz), 8.03 (2H, m), 7.76 (5H, m), 7.40 (1H, d, J=8.4 Hz), 7.20 (1H, s), 7.07 (1H, d, 4.8 Hz), 6.22 (1H, s), 3.03 (1H, m), 2.66 (4H, m), 2.53 (3H, s), 2.18 (2H, m), 1.60 (2H, m).

TBI-900, 5-(4-Fluorophenyl)-3-(4-tetrahydropyranyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.46 (1H, d, J=2.4 Hz), 7.69 (1H, d, J=7.8 Hz), 7.67 (1H, dd, J=7.8, 2.4 Hz), 7.43 (2H, dd, J=8.4, 8.1 Hz), 7.31 (2H, dd, J=8.4, 5.1 Hz), 7.17 (3H, m), 6.74 (1H, s), 6.49 (1H, d, J=7.5 Hz), 5.24 (1H, s), 3.97 (2H, m), 3.40 (3H, m), 2.58 (3H, s), 1.66 (4H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, J=250 Hz), 153.5, 151.1, 150.7, 144.3, 143.8, 135.7, 135.2, 133.9, 133.4, 131.5, 130.8, 130.7, 130.1, 129.5, 128.3, 127.7, 123.1 (d, J=12 Hz), 118.4 (d, J=23 Hz), 114.0, 99.0, 88.8, 66.1, 54.3, 33.4, 23.8. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₇FN₅O: 480.2199: found: 480.2206.

TBI-901, 5-(4-Fluorophenyl)-3-(N-methyl-4-piperidyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.47 (1H, d, J=2.4 Hz), 7.74 (1H, d, J=7.8 Hz), 7.68 (1H, dd, J=7.8, 2.4 Hz), 7.46 (2H, dd, J=8.4, 8.1 Hz), 735 (2H, dd, J=8.4, 5.1 Hz), 7.23 (3H, m), 6.79 (1H, s), 6.56 (1H, d, J=7.8 Hz), 5.27 (1H, s), 3.18 (1H, m), 2.87 (2H, m), 2.57 (3H, s), 2.36 (3H, s), 1.74 (2H, m), 1.28 (4H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 162.9 (d, J=250 Hz), 153.6, 152.5, 151.0, 144.2, 143.8, 135.7, 135.1, 134.0, 133.4, 131.5, 130.7, 130.6, 129.5, 129.3, 128.4, 127.7, 123.2 (d, J=23 Hz), 118.4 (d, J=23 Hz), 114.1, 99.4, 88.7, 60.51, 51.8, 45.3, 31.9, 23.5. HRMS (EST-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₃₀FN₆: 493.2516; found: 493.2512.

TBI-902, 5-(4-Fluorophenyl)-3-(N-methyl-3-piperidylmethyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.45 (1H, d, J=2.4 Hz), 7.70 (1H, d, J=7.5 Hz), 7.67 (1H, dd, J=7.5, 2.7 Hz), 7.42 (2H, dd, J=8.7, 8.1 Hz), 7.33 (2H, dd, J=8.4, 4.8 Hz), 7.16 (3H, m), 6.73 (1H, s), 6.47 (1H, d, J=7.8 Hz), 5.22 (1H, s), 3.00 (2H, m), 2.91 (1H, d, J=10.5 Hz), 2.79 (1H, d, J=10.5 Hz), 2.56 (3H, s), 2.26 (3H, s), 1.86 (2H, u J=9.6 Hz), 1.66 (4H, m), 1.26 (1H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, J=250 Hz), 153.5, 151.6, 149.8. 143.9, 143.6, 135.8, 135.1, 133.8, 133.0, 131.0, 130.7, 130.4, 130.3, 129.9, 128.6, 128.3, 123.4 (d, J=12 Hz), 118.8 (d, J=23 Hz), 114.1, 98.9, 89.0, 60.9, 56.3, 54.1, 46.7, 38.1, 28.6, 25.2, 23.8. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₂FN₆: 507.2672; found: 507.2668.

TBI-904, 5-(4-Fluorophenyl)-3-(N-isobutyl-4-piperidyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.45 (1H, d, J=2.4 Hz), 7.70 (1H, d, J=7.5 Hz), 7.68 (1H, dd, J=7.5, 2.7 Hz), 7.44 (2H, dd, J=8.7, 8.1 Hz), 7.35 (2H, dd, J=8.4, 4.8 Hz), 7.17 (3H, m), 6.74 (1H, s), 6.48 (1H, d, J=7.8 Hz), 5.25 (1H, s), 3.12 (1H, m), 2.78 (2H, m), 2.57 (3H, s), 2.07 (2H, m), 1.90 (2H, m), 1.70 (4H, m), 1.46 (1H, m), 0.90 (6H, d, J=6.0 Hz). ¹³C NMR (100 MHz, CDCl₃) δ: 162.2 (d, J=250 Hz), 153.4, 151.0, 149.8, 144.4, 143.7, 135.7, 135.1, 134.1, 133.5, 131.6, 130.9, 129.4, 128.8, 128.3, 127.6, 123.1 (d, J=24 Hz), 118.4 (d, J=23 Hz), 113.9, 98.9, 89.1, 67.1, 56.1, 52.5, 32.8, 25.7, 23.8, 21.0. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₃H₃₆FN₆: 535.2985; found: 535.2982.

TBI-905, 5-(4-Fluorophenyl)-3-cyclohexylimino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.45 (1H, d, J=2.4 Hz), 7.70 (1H, d, J=7.5 Hz), 7.67 (1H, dd, J=7.5, 2.7 Hz), 7.43 (2H, dd, J=8.7, 8.1 Hz), 7.35 (2H, dd, J=8.4, 4.8 Hz), 7.13 (3H, m), 6.72 (1H, s), 6.48 (1H, d, J=7.8 Hz), 5.26 (1H, s), 3.07 (1H, m), 2.57 (3H, s), 1.74 (2H, d, J=10.0 Hz), 1.61 (2H, d, J=10.0 Hz), 1.38 (3H, m), 1.23 (3H, m), ¹³C NMR (100 MHz, CDCl₃) δ: 162.2 (d, J=250 Hz), 153.3, 151.1, 150.6, 144.4, 143.7, 135.7, 135.0, 134.1, 133.5, 131.6, 130.9, 130.8, 129.4, 128.2, 127.5, 123.1 (d, J=32 Hz), 118.3 (d, J=23 Hz), 113.8, 98.9, 89.3, 58.0, 33.6, 25.8, 24.7, 23.8. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₂₉FN₅: 478.2407; found: 478.2405.

TBI-906, 5-(4-Fluorophenyl)-3-(1′,4′-trans-4-hydroxycyclohexyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.44 (1H, d, J=2.4 Hz), 7.70 (1H, d, J=7.5 Hz), 7.68 (1H, dd, J=7.5, 2.7 Hz), 7.43 (2H, dd, J=8.7, 8.1 Hz), 7.34 (2H, dd, J=8.4, 4.8 Hz), 7.16 (3H, m), 6.73 (1H, s), 6.49 (1H, d, J=7.8 Hz), 5.24 (1H, s), 3.66 (1H, m), 3.07 (1H, m), 2.56 (3H, s), 2.00 (2H, d, J=9.6 Hz), 1.68 (2H, d, J=9.6 Hz), 1.45 (2H, m), 1.24 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 162.2 (d, J=250 Hz), 153.4, 151.3, 150.8, 144.3, 143.6, 135.6, 135.1, 134.0, 133.4, 131.5, 130.8, 130.7, 129.5, 128.2, 127.7, 123.1 (d, J=23 Hz), 118.4 (d, J=23 Hz), 113.9, 98.9, 89.0, 69.9, 57.2, 33.8, 30.7, 23.8. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₂₉FN₅O: 494.2356; found: 494.2352.

TBI-907, 5-(4-Fluorophenyl)-3-(1′,4′-trans-4-methoxycyclohexyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.44 (1H, d, J=2.4 Hz), 7.70 (1H, d, J=7.5 Hz), 7.68 (1H, dd, 7.5, 2.7 Hz), 7.54 (2H, dd, J=8.7, 8.1 Hz), 7.43 (2H, dd, J=8.4, 4.8 Hz), 7.16 (3H, m), 6.73 (1H, s), 6.51 (1H, d, J=7.8 Hz), 5.25 (1H, s), 3.36 (3H, s), 3.16 (1H, m), 3.09 (1H, m), 2.56 (3H, s), 2.07 (2H, J=10.1 Hz), 1.71 (2H, d, J=10.1 Hz), 1.45 (2H, m), 1.17 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 162.2 (d, J=250 Hz), 153.4, 151.3, 150.8, 144.2, 143.7, 135.4, 135.1, 134.0, 133.2, 131.5, 130.8, 130.7, 128.8, 128.3, 127.3, 123.7 (d, J=23 Hz), 118.4 (d, J=23 Hz), 113.9, 98.9, 89.1, 78.4, 63.7, 55.8, 30.5, 30.0, 23.8. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₁FN₅O: 508.2513; found: 508,2513.

TBI-908, 5-(4-Fluorophenyl)-3-cyclopropylimino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.41 (1H, d, J=2.4 Hz), 7.65H, dd, J=8.7, 8.1 Hz), 7.39 (2H, dd, J=8.4, 4.8 Hz), 7.36 (2H, m), 7.15 (3H, m), 6.66 (1H, s), 6.43 (1H, d, J=7.8 Hz), 5.54 (1H, s), 2.73 (1H, m), 2.56 (3 s), 0.89 (2H, m), 0.81 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 162.2 (d, J=250 Hz), 153.4, 151.3, 150.8, 144.2, 143.7, 135.4, 135.1, 134.0, 133.2, 131.5, 130.8, 130.7, 128.8, 128.3, 127.3, 123.7 (d. J=23 Hz), 118.4 (d, J=23 Hz), 113.9, 989, 89.1, 32.8, 23.8, 9.9. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₃FN₅: 436.1937; found: 436.1932.

TBI-910, 5-(4-Fluorophenyl)-3-(1-methylethyl)imino-2-(6-acetamino-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.29 (1H, d, J=2.4 Hz), 8.22 (1H, d, J=8.7 Hz), 7.75 (1H, dd, J=8.7, 2.4 Hz), 7.68 (1H, d, J=7.2 Hz), 7.42 (2H, dd, J=9.0, 8.1 Hz), 7.34 (2H, dd, J=8.4, 4.8 Hz), 7.15 (2H, m), 6.70 (1H, s), 6.46 (1H, d, J=7.8 Hz), 5.27 (1H, s), 3.45 (1H, m), 2.23 (3H, s), 1.09 (6H, d, J=6.0 Hz). ¹³C NMR (100 MHz, CDCl₃) 168.2, 162.8 (d, J=250 Hz), 150.9, 150.4, 147.1, 144.4, 142.1, 135.7, 135.1, 133.5, 133.2, 132.1, 131.7, 128.2, 127.6, 122.9, 118.5 (d, J=22 Hz), 114.0 (d, J=7.5 Hz), 98.8, 89.0, 49.4, 24.7, 23.5. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₆FN₆O: 481.2152; found: 481.2148.

TBI-911, 5-(4-Fluorophenyl)-3-(4-tetrahydropyranyl)imino-2-(6-acetamino-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.29 (1H, d, J=2.4 Hz), 8.23 (1H, d, J=8.7 Hz), 7.75 (1H, dd, J=8.7, 2.4 Hz), 7.70 (1H, d, J=7.2 Hz), 7.42 (2H, t, J=8.4 Hz), 7.33 (2H, dd, J=8.4, 4.8 Hz), 7.17 (2H, m), 6.73 (1H, s), 6.49 (1H, d, J=7.8 Hz), 5.24 (1H, s), 3.97 (2H, m), 3.45 (3H, m), 2.23 (3H, s), 1.65 (4H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 168.3, 162.8 (d, J=250 Hz), 151.1, 150.6, 147.4, 144.3, 142.2, 135.7, 135.3, 133.4, 132.9, 132.1, 131.5, 130.8, 130.7, 128.4, 127.8, 123.1, 118.4 (d, J=23 Hz), 114.0 (d, J=7.5 Hz), 99.0, 88.8, 66.1, 54.3, 33.4, 24.6. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₂₈FN₆O₂: 523.2258; found: 523.2252.

TBI-912, 5-(4-Fluorophenyl)-3-(N-methyl-4-piperidyl)imino-2-(6-acetamino-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.29 (1H, d, J=2.4 Hz), 8.23 (1H, d, J=8.4 Hz), 7.75 (1H, dd, J=8.7, 2.4 Hz), 7.72 (1H, d, J=7.2 Hz), 7.44 (2H, dd, J=8.4, 8.1 Hz), 7.33 (2H, dd, J=8.7, 4.8 Hz), 7.20 (2H, m), 6.74 (1H, s), 6.52 (1H, d, J=7.2 Hz), 5.26 (1H, s), 3.18 (1H, m), 2.87 (2H, m), 2.36 (3H, s), 2.23 (3H, s), 1.74 (2H, m), 1.28 (4H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 168.3, 162.9 (d, J=250 Hz), 151.4, 150.7, 147.4, 144.2, 142.4, 135.9, 135.2, 133.4, 132.9, 132.1, 131.4, 130.7, 130.6, 128.5, 128.0, 123.5, 118.5 (d, J=23 Hz), 114.1 (d, J=7.5 Hz), 99.2, 89.0, 60.51, 53.5, 45.9, 31.9, 24.7. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₁FN₇O: 536.2574; found: 536.2576.

TBI-913, 5-(4-Fluorophenyl)-3-(N-isobutyl-4-piperidyl)imino-2-(6-acetamino-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.29 (1H, d, J=2.4 Hz), 8.22 (1H, d, J=8.4 Hz), 7.75 (1H, dd, J=8.7, 2.4 Hz), 7.72 (1H, d, J=7.2 Hz), 7.48 (2H, dd, J=8.4, 8.1 Hz), 7.33 (2H, dd, J=8.7, 4.8 Hz), 6.99 (2H, m), 6.78 (1H, s), 6.55 (1H, d, J=7.2 Hz), 5.31 (1H, s), 3.17 (1H, m), 2.81 (2H, m), 2.22 (3H, s), 1.96 (2H, m), 1.90 (2H, m), 1.73 (4H, m), 1.49 (1H, m), 0.89 (6H, d, J=6.0 Hz). ¹³C NMR (100 MHz, CDCl₃) δ: 168.5, 163.0 (d, J=250 Hz), 151.3, 150.7, 147.5, 144.0, 142.3, 135.8, 135.2, 133.2, 132.8, 132.3, 131.2, 130.6, 130.4, 128.7, 128.0, 123.6, 118.5 (d, J=23 Hz), 114.2 (d, J=7.5 Hz), 99.3, 89.2, 66.7, 52.5, 45.4, 32.0, 25.6, 24.6, 20.9. HRMS (ESI-TOF⁺): m/z. [M+H]⁺ calcd for C₃₄H₃₇FN₇O: 578.3044; found: 578.3041.

TBI-915, 5-(4-Fluorophenyl)-3-(1′,4′-trans-4-methoxycyclohexyl)imino-2-(6-acetamino-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.27 (1H, d, J=2.4 Hz), 8.23 (1H, d, J=8.4 Hz), 7.74 (1H, dd, J=8.7, 2.4 Hz), 7.72 (1H, d, J=7.5 Hz), 7.43 (2H, dd, J=8.7, 8.1 Hz), 7.33 (2H, dd, J=8.7, 4.8 Hz), 7.20 (2H, m), 6.74 (1H, s), 6.53 (1H, d, J=7.5 Hz), 5.28 (1H, s), 3.36 (3H, s), 3.19 (1H, m), 3.09 (1H, m), 2.23 (3H, s), 2.07 (2H, d, J=10.1 Hz), 1.71 (2H, d, J=10.1 Hz), 1.45 (2H, m), 1.17 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 168.4, 163.0 (d, J=250 Hz), 151.5, 150.6, 147.4, 144.1, 142.1, 135.7, 135.2, 133.2, 132.8, 132.3, 131.2, 130.6, 130.4, 128.8, 127.9, 123.4, 118.5 (d, J=23 Hz), 114.2 (d, J=7.5 Hz), 99.9, 89.2, 78.2, 56.2, 55.8, 30.7, 30.0, 24.6. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₂H₃₂FN₆O₂: 551.2571: found: 551.2571.

TBI-916, 5-(4-Fluorophenyl)-3-cyclohexylimino-2-(6-acetamino-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.28 (1H, d, J=2.4 Hz), 8.21 (1H, d, J=9.0 Hz), 7.74 (1H, dd, J=9.0, 2.4 Hz), 7.68 (1H, d, J=7.5 Hz), 7.43 (2H, dd, J=8.7, 8.1 Hz), 7.33 (2H, dd, J=8.7, 4.8 Hz), 7.15 (2H, m), 6.70 (1H, s), 6.48 (1H, d, J=7.5 Hz), 5.25 (1H, s), 3.06 (1H, m), 2.23 (3H, s), 1.74 (2H, d, J=10.0 Hz), 1.61 (2H, d, J=10.0 Hz), 1.37 (3H, m), 1.21 (3H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 168.4, 163.0 (d, J=250 Hz), 151.5, 150.6, 147.4, 144.1, 142.1, 135.7, 135.2, 133.2, 132.8, 132.3, 131.2, 130.6, 130.4, 128.8, 127.9, 123.4, 118.5 (d, J=23 Hz), 114.2 (d, J=7.5 Hz), 99.9, 89.2, 58.0, 33.6, 25.8, 24.7, 24.6. HRMS (ESI-TOF⁺): m/z calcd for C₃₁H₃₀FN₆O: 521.2465: found: 521.2465.

TBI-917, 5-(4-Fluorophenyl)-3-(1′,4′-trans-4-hydroxycyclohexyl)imino-2-(6-acetamino-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.28 (1H, d, 0.1-2.4 Hz), 8.22 (1H, d, J=9.0 Hz), 7.74 (1H, dd, J=9.0, 2.4 Hz), 7.69 (1H, d, J=7.5 Hz), 7.43 (2H, dd, J=8.7, 8.1 Hz), 7.33 (2H, dd, J=8.7, 4.8 Hz), 7.16 (2H, m), 6.70 (1H, s), 6.49 (1H, d, J=7.5 Hz), 5.24 (1H, s), 3.69 (1H, m), 3.07 (1H, m), 2.23 (3H, s), 2.01 (2H, d, J=9.6 Hz), 1.68 (2H, d, J=9.6 Hz), 1.46 (2H, m), 1.25 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 168.2, 162.8 (d, J=250 Hz), 151.2, 150.8, 147.2, 144.3, 142.2, 135.7, 135.1, 133.4, 133.0, 132.0, 131.6, 130.8, 130.7, 128.3, 127.7, 123.0, 118.4 (d, J=23 Hz), 114.0 (d, J=7.5 Hz), 98.9, 89.0, 70.0, 57.2, 33.7, 31.2, 24.7. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₀FN₆O₂: 537.2414; found: 537.2419.

TBI-920, 5-(4-Fluorophenyl)-3-cyclohexylimino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.58 (1H, d, J=2.4 Hz), 8.32 (1H, dd, J=4.8, 1.2 Hz), 7.77 (1H, dd, J=8.4, 1.2 Hz), 7.69 (1H, d, J=7.5 Hz), 7.43 (2H, m), 7.35 (2H, m), 7.31 (1H, m), 7.30 (1H, m), 7.16 (2H, m), 6.84 (1H, s), 6.49 (1H, d, 0.1-7.5 Hz), 5.26 (1H, s), 3.09 (1H, m), 1.74 (2H, m), 1.61 (3H, m), 1.38 (2H, m), 1.15 (3H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, J=250 Hz), 151.0, 150.5, 144.2, 143.9, 143.7, 136.9, 135.7, 135.1, 133.5, 131.7, 130.9, 130.8, 128.3, 127.8, 127.7, 123.6, 122.9, 118.4 (d, J=23 Hz), 113.9 (d, J=7.5 Hz), 99.4, 89.3, 57.9, 33.7, 25.7, 24.7. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₇FN₅: 464.2250; found: 464.2252.

TBI-921, 5-(4-Fluorophenyl)-3-(1′,4′-trans-4-hydroxycyclohexyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.57 (1H, d, J=2.4 Hz), 8.33 (1H, dd, J=4.8, 1.2 Hz), 7.79 (1H, dd, J=8.4, 1.2 Hz), 7.71 (1H, d, J=7.5 Hz), 7.43 (2H, m), 7.36 (2H, m), 7.31 (1H, m), 7.17 (2H, m), 6.85 (1H, s), 6.50 (1H, d, J=7.5 Hz), 5.25 (1H, s), 3.70 (1H, m), 3.08 (1H, m), 2.00 (2H, m), 1.68 (2H, m), 1.43 (2H, m), 1.25 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, J=250 Hz), 151.2, 150.8, 144.3, 143.9, 143.5, 136.8, 135.6, 135.2, 133.4, 131.7, 130.8, 130.7, 128.4, 127.9, 123.7, 123.1, 118.4 (d, J=23 Hz), 114.0 (d, J=7.5 Hz), 99.5, 89.0, 70.0, 57.2, 33.7, 31.2. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₇FN₅O: 480.2200; found: 480.2199.

TBI-922, 5-(4-Fluorophenyl)-3-cyclopropylimino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.54 (1H, d, J=2.4 Hz), 8.31 (1H, dd, J=4.8, 1.2 Hz), 7.74 (1H, dd, J=8.4, 1.2 Hz), 7.66 (1H, d, J=7.5 Hz), 7.44 (3H, m), 7.28 (2 dd, J=8.4, 4.8 Hz), 7.13 (2H, m), 6.78 (1H, s), 6.42 (1H, d, J=7.5 Hz), 5.53 (1H, s), 2.73 (1H, m), 0.88 (2H, m), 0.80 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, J=250 Hz), 152.4, 151.2, 144.3, 143.9, 143.4, 136.6, 135.7, 134.9, 133.4, 131.9, 130.9, 130.8, 128.2, 127.8, 123.6, 122.9, 118.5 (d, J=23 Hz), 113.9 (d, J=7.5 Hz), 99.4, 89.4, 32.8, 9.9. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₆H₂₁FN₅: 422.1781; found: 422.1780.

TBI-923, 5-(4-Fluorophenyl)-3-cyclobutylimino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.60 (1H, d, J=2.4 Hz), 8.33 (1H, dd, J=4.8, 1.2 Hz), 7.77 (1H, dd, J=8.4, 1.2 Hz), 7.70 (1H, d, J=7.5 Hz), 7.43 (3H, m), 7.31 (2H, dd, J=8.4, 4.8 Hz), 7.17 (2H, m), 6.83 (1H, s), 6.49 (1H, d, J=7.5 Hz), 5.09 (1H, s), 3.89 (1H, m), 2.17 (2H, m), 2.04 (2H, m), 1.69 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, 250 Hz), 151.2, 150.9, 144.3, 143.9, 143.5, 136.7, 135.7, 134.7, 133.4, 131.6, 130.9, 130.8, 128.3, 127.8, 123.6, 123.1, 118.4 (d, J=23 Hz), 113.9 (d, J=7.5 Hz), 99.5, 90.5, 54.8, 31.9, 16.0. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₃FN₅: 436.1937; found: 436.1936.

TBI-930, 5-(4-Fluorophenyl)-3-(1-methylethyl)imino-2-(6-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.15 (1H, d, J=2.4 Hz), 7.64 (2H, m), 7.42 (2H, m), 7.34 (2H, m), 7.13 (2H, m), 6.78 (1H, d, J=8.7 Hz), 6.50 (1H, s), 6.46 (1H, d, J=7.8 Hz), 5.27 (1H, s), 3.96 (3H, s), 3.46 (1H, m), 1.09 (6H, d, J=6.3 Hz). ¹³C NMR (100 MHz, CDCl₃) δ: 162.7 (d, J=250 Hz), 161.2, 150.9, 150.5, 145.8, 142.4, 135.6, 135.2, 135.0, 133.5, 131.5, 130.9, 130.8, 130.1, 128.0, 127.3, 122.8, 118.4 (d, J=23 Hz), 113.8, 111.0, 98.0, 89.0, 53.6, 49.3, 22.7.

TBI-931, 5-(4-Fluorophenyl)-3-cyclopropylmino-2-(6-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃)₆: 8.10 (1H, d, J=2.4 Hz), 7.62 (2H, m), 7.44 (2H, m), 7.36 (2H, m), 7.12 (2H, m), 6.79 (1H, d, J=8.7 Hz), 6.43 (1H, s), 6.42 (1H, d, J=7.8 Hz), 5.53 (1H, s), 3.95 (3H, s), 2.73 (1H, m), 0.87 (2H, m), 0.79 (2H, m). ¹³C NMR (100 MHz, CDCl₃) 162.7 (d, J=250 Hz), 161.3, 152.6, 151.2, 145.8, 142.7, 135.8, 135.3, 134.9, 133.6, 131.7, 130.9, 130.8, 130.0, 128.0, 127.3, 122.8, 118.4 (d, J=23 Hz), 113.8, 111.1, 98.1, 89.4, 53.6, 32.8, 9.8.

TBI-932, 5-(4-Fluorophenyl)-3-cyclohexylimino-2-(6-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.15 (1H, d, J=2.4 Hz), 7.63 (2H, m), 7.42 (2H, m), 7.32 (2H, m), 7.13 (2H, m), 6.78 (1H, d, J=8.7 Hz), 6.49 (1H, s), 6.47 (1H, d, J=7.8 Hz), 5.24 (1H, s), 3.95 (3H, s), 3.07 (1H, m), 1.73 (2H, m), 1.61 (3H, m), 1.33 (2H, m), 1.21 (3H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 162.7 (d, J=250 Hz), 161.2, 151.1, 150.6, 145.9, 142.4, 135.6, 135.0, 134.9, 133.6, 131.5, 130.9, 130.8, 130.2, 128.1, 127.2, 122.8, 118.4 (d, J=23 Hz), 113.8, 111.0, 98.0, 89.3, 58.0, 53.6, 33.6, 25.8, 24.7.

TBI-933, 5-(4-Fluorophenyl)-3-(1′,4′-trans-4-methoxycyclohexyl)imino-2-(6-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) 8.14 (1H, d, J=2.4 Hz), 7.68 (2H, m), 7.41 (2H, m), 7.32 (2H, m), 7.15 (2H, m), 6.78 (1H, d, J=8.7 Hz), 6.50 (1H, s), 6.48 (1H, d, J=7.8 Hz), 5.24 (1H, s), 3.96 (3H, s), 3.36 (3H, s), 3.19 (1H, m), 3.08 (1H, m), 2.08 (2H, m), 1.70 (2H, m), 1.40 (2H, m), 1.20 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 162.7 (d, J=250 Hz), 161.2, 151.3, 150.9, 145.9, 142.5, 135.7, 135.1, 134.9, 133.5, 131.5, 130.8, 130.7, 130.2, 128.2, 127.4, 122.9, 118.4 (d, J=23 Hz), 113.9, 111.0, 98.1, 89.0, 57.4, 55.8, 53.6, 31.2, 30.0.

TBI-934, 5-(4-Fluorophenyl)-3-cyclobutylimino-2-(6-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.13 (1H, d, J=2.4 Hz), 7.63 (2H, m), 7.43 (2H, m), 7.30 (2H, m), 7.12 (2H, m), 6.77 (1H, d, J=8.7 Hz), 6.48 (1H, s), 6.46 (1H, d, J=7.8 Hz), 5.06 (1H, s), 3.93 (3H, s), 3.87 (1H, m), 2.15 (2H, m), 2.03 (2H, m), 1.73 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 162.7 (d, J=250 Hz), 161.1, 151.2, 150.6, 145.5, 142.2, 135.5, 134.9, 134.4, 133.4, 131.2, 130.8, 130.7, 130.0, 128.0, 127.3, 122.8, 118.2 (d, J=23 Hz), 113.8, 110.9, 98.0, 90.4, 54.7, 53.4, 31.8, 15.9.

TBI-935, 5-(4-Fluorophenyl)-3-(4-tetrahydropyranyl)imino-2-(6-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.15 (1H, d, J=2.4 Hz), 7.65 (2H, m), 7.43 (2H, m), 7.34 (2H, m), 7.16 (2H, m), 6.79 (1H, d, J=8.7 Hz), 6.53 (1H, s), 6.48 (1H, d, J=7.5 Hz), 5.24 (1H, s), 3.99 (2H, m), 3.96 (3 s), 3.40 (3H, m), 1.65 (4H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 162.7 (d, J=250 Hz), 161.3, 151.2, 150.7, 145.9, 142.5, 135.7, 135.1, 134.4, 133.5, 131.4, 130.8, 130.7, 130.0, 128.2, 127.4, 123.0, 118.2 (d, J=23 Hz), 114.0, 111.1, 98.2, 88.8, 66.1, 54.4, 53.4, 33.4.

TBI-940, 5-(4-Fluorophenyl)-3-cyclopropylimino-2-(4-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.53 (1H, s), 8.26 (1H, d, 4.8 Hz), 7.55 (1H, d, J=7.5 Hz), 7.35 (2H, t, J=8.4 Hz), 7.29 (2H, m), 7.10 (2H, d, J=4.8 Hz), 7.05 (2H, m), 6.36 (1H, d, J=7.5 Hz), 6.16 (1H, s), 5.47 (1H, s), 2.69 (1H, m), 2.19 (3H, s), 0.83 (2H, m), 0.78 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 162.7 (d, J=250 Hz), 152.3, 151.2, 146.7, 146.4, 145.2, 142.5, 135.7, 135.3, 134.9, 133.6, 131.8, 130.9, 130.8, 128.1, 127.4, 122.8, 118.5 (d, J=23 Hz), 113.8, 98.8, 89.3, 32.8, 17.4, 10.0.

TBI-950, 5-(4-Trifluoromethoxyphenyl)-3-(4-tetrahydropyranyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.47 (1H, s), 7.70 (3H, m), 7.60 (2H, d, J=8.7 Hz), 7.41 (2H, d, J=8.7 Hz), 7.19 (2H, m), 6.74 (1H, s), 6.51 (1H, d, J=8.1 Hz), 5.17 (1H, s), 3.97 (2H, m), 3.36 (3H, m), 1.63 (4H, m).

TBI-951, 5-(4-Trifluoromethoxyphenyl)-3-(1-methylethyl)imino-2-(pyrimidin-2-yl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 9.55 (1H, br. s), 8.36 (2H, d, J=4.8 Hz), 8.30 (1H, s), 7.58 (1H, d, J=7.5 Hz), 7.40 (2H, d, J=7.8 Hz), 7.23 (2H, d, 7.8 Hz), 6.99 (2H, m), 6.64 (1H, s), 6.24 (1H, d, J=7.5 Hz), 5.03 (1H, s), 3.24 (1H, m), 1.06 (61-1, d, J=6.0 Hz).

TBI-952, 5-(4-Trifluoromethoxyphenyl)-3-(1-methylethyl)imino-2-(2-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 9.31 (1H, br. s), 8.38 (1H, d, J=3.9 Hz), 8.28 (1H, s), 7.76 (1H, d 7.5 Hz), 7.58 (2H, d, J=7.8 Hz), 7.42 (2H, d, J=7.8 Hz), 7.16 (2H, m), 6.98 (1H, d, J=8.4 Hz), 6.85 (1H, m), 6.44 (1H, d, J=7.5 Hz), 5.21 (1H, s), 3.44 (1H, m), 1.07 (6H, d, J=6.0 Hz).

TBI-953, 5-(4-Trifluoromethoxyphenyl)-3-(1-methylethyl)imino-2-(pyrazin-2-yl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.44 (1H, br. s), 8.31 (1H, s), 8.28 (1H, d, J=2.4 Hz), 8.05 (1H, d, J=2.4 Hz), 7.78 (1H, d, J=9.3 Hz), 7.59 (2H, d, J=7.8 Hz), 7.42 (2H, d, J=7.8 Hz), 7.19 (2H, m), 6.45 (1H, d, J=9.3 Hz), 5.30 (1H, s), 5.22 (1H, s), 3.43 (1H, m), 1.10 (6H, d, J=6.0 Hz).

TBI-954, 5-(4-Trifluoromethoxyphenyl)-3-(1-methylethyl)imino-2-(3-nitro-2-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 12.24 (1H, br. s), 8.73 (1H, s), 8.66 (1H, d, J=4.5 Hz), 8.56 (1H, d, J=8.1 Hz), 7.78 (1H, d, J=9.3 Hz), 7.59 (2H, d, J=8.4 Hz), 7.42 (2H, d, J=8.4 Hz), 7.19 (2H, m), 6.95 (1H, dd, J=8.1, 4.5 Hz), 6.44 (1H, d, J=9.3 Hz), 5.23 (1H, s), 3.45 (1H, m), 1.14 (6H, d, J=6.0 Hz).

TBI-960, 5-(4-Chlorophenyl)-3-(4-tetrahydropyranyl)imino-2-(pyrimidin-5-yl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 9.67 (1H, br. s), 9.00 (2H, s), 8.67 (1H, s), 7.71 (1H, d, J=7.5 Hz), 7.70 (2H, d, J=7.5 Hz), 7.27 (2H, d, J=7.5 Hz), 7.14 (2H, m), 6.47 (1H, d, J=7.5 Hz), 5.19 (1H, s), 3.96 (2H, m), 3.35 (3H, m), 1.61 (4H, m).

TBI-961, 5-(4-Chlorophenyl)-3-cyclohexylimino-2-(pyrimidin-5-yl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 9.68 (1H, br. s), 9.01 (2H, s), 8.67 (1H, s), 7.73 (1H, d, J=7.5 Hz), 7.69 (2H, d, J=7.5 Hz), 7.27 (2H, d, J=7.5 Hz), 7.11 (2H, m), 6.43 (1H, d, J=7.5 Hz), 5.19 (1H, s), 3.05 (1H, m), 1.73 (2), 1.57 (3 m), 1.33 (2 m), 1.19 (3H, m).

TBI-980, 5-(3-Chlorophenyl)-3-(4-tetrahydropyranyl)imino-2-(pyrimidin-5-yl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 9.67 (1H, br. s), 9.00 (2H, s), 8.67 (1H, s), 7.70 (3H, m), 7.36 (1H, s), 7.24 (1H, m), 7.15 (2H, m), 6.49 (1H, d, J=7.5 Hz), 6.39 (1H, s), 5.19 (1H, s), 3.96 (2H, m), 3.35 (3H, m), 1.61 (4H, m).

TBI-80A, 5-(3-Chlorophenyl)-3-(4-tetrahydropyranyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.47 (1H, s), 7.68 (4H, m), 7.38 (1H, s), 7.27 (1H, m), 7.18 (3H, m), 6.74 (1H, s), 6.53 (1H, d, J=7.5 Hz), 5.26 (1H, s), 3.98 (2H, m), 3.40 (2H, m), 2.84 (1H, m), 2.57 (3H, s), 1.67 (4H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 153.8, 153.7, 151.2, 150.7, 144.3, 143.9, 138.6, 136.8, 135.7, 134.7, 133.9, 132.3, 131.0, 130.2, 129.6, 129.3, 128.4, 127.8. 127.2, 123.2, 114.0, 99.0, 89.1, 66.9, 54.5, 34.3, 23.8.

TBI-80B, 5-(3-Chlorophenyl)-3-cyclohexylimino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.45 (1H, s), 7.67 (4H, m), 7.38 (1H, s), 7.28 (1H, m), 7.16 (3H, m), 6.7 ((1H, s), 6.50 (1H, d, J=7.5 Hz), 5.25 (1H, s), 3.08 (1H, m), 1.76 (2H, m), 1.61 (3H, m), 1.35 (2H, m), 1.23 (3H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 153.8, 153.3, 151.0, 150.6, 144.4, 143.7, 138.7, 136.7, 135.6, 134.5, 134.0, 132.2, 131.2, 130.2, 129.4, 128.2, 127.6, 127.3, 123.2, 123.0, 113.8, 98.8, 89.5, 58.1, 33.6, 25.8, 24.7, 23.8.

TBI-80C, 5-(3-Chlorophenyl)-3-(1,3-dimethoxyisopropyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.44 (1H, s), 7.67 (4H, m), 7.37 (1H, s), 7.28 (1H, m), 7.16 (3H, m), 6.74 (1H, s), 6.49 (1H, d, J=7.5 Hz), 5.47 (1H, s), 3.73 (1H, s), 3.52 (2H, m), 3.44 (2H, m), 3.36 (3H, s), 3.28 (3H, s), 2.56 (3H, s). ¹³C NMR (100 MHz, CDCl₃) δ: 153.5, 153.3, 151.0, 150.7, 144.4, 143.7, 138.7, 136.7, 135.6, 134.5, 134.0, 132.2, 131.2, 130.2, 129.4, 128.2, 127.6, 127.3, 123.2, 123.1, 114.0, 99.0, 90.1, 74.6, 74.3, 59.1, 59.0, 58.4, 23.8.

TBI-810, 5-(3-Chlorophenyl)-3-(1-methylethyl)imino-2-(3-pyrid amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.55 (1H, s), 8.33 (1H, d, J=4.8 Hz), 7.76 (1H, d, J=7.5 Hz), 7.66 (3H, m), 7.40 (1H, s), 7.29 (2H, m), 7.15 (2H, m), 6.78 (1H, s) 6.44 (1H, d, J=7.5 Hz), 5.55 (1H, s), 3.45 (1H, m), 1.09 (6H, d, J=6.0 Hz). ¹³C NMR (100 MHz, CDCl₃) δ: 152.3, 151.2, 144.4, 144.0, 143.4, 138.7, 136.8, 136.6, 135.6, 134.5, 132.4, 131.5, 130.1, 129.4, 128.2, 128.1, 127.8, 127.4, 123.6, 123.0, 113.8, 99.4, 89.6, 49.4, 23.6.

TBI-811, 5-(3-Chlorophenyl)-3-(1′,4′-trans-4-hydroxycyclohexyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.49 (1H, s), 8.25 (1H, d, J=3.7 Hz), 8.03 (1H, s), 7.72 (1H, d, J=7.5 Hz), 7.62 (3H, m), 7.31 (1H, s), 7.25 (2H, m), 7.12 (2H, m), 6.77 (1H, s), 6.46 (1H, d, J=7.5 Hz), 5.18 (1H, s), 3.71 (1H, m), 3.05 (1H, m), 1.96 (2H, m), 1.69 (2H, m), 1.47 (2H, m), 1.25 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 151.2, 150.7, 144.1, 143.7, 143.4, 138.5, 136.7, 135.5, 134.7, 132.2, 131.1, 130.1, 129.2, 128.3, 128.0, 127.1, 125.0, 123.7, 123.2, 119.2, 113.9, 99.5, 89.2, 70.1, 57.3, 33.7, 31.2

TBI-812, 5-(3-Chlorophenyl)-3-cyclopropylimino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.55 (1H, d, 0.1-1.7 Hz), 8.33 (1H, d, J=4.0 Hz), 8.03 (1H, s), 7.76 (1H, d, J=8.5 Hz), 7.65 (3H, m), 7.39 (1H, s), 7.28 (2H, m), 7.15 (2H, m), 6.78 (1H, s), 6.44 (1H, d, J=7.5 Hz), 5.55 (1H, s), 2.75 (1H, m), 0.89 (2H, m), 0.82 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 152.3, 151.2 144.4, 144.0, 143.4, 138.7, 136.8, 136.6, 1356, 134.5, 132.4, 131.5, 130.1, 129.4, 128.3, 128.1, 127.8, 127.4, 123.6, 123.0, 113.8, 99.4, 89.6, 32.9, 10.0.

TBI-814, 5-(3-Chlorophenyl)-3-cyclobutylimino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.59 (1H, d, J=2.4 Hz), 8.33 (1H, d, J=4.8 Hz), 8.03 (1H, s), 7.78 (1H, d, J=8.4 Hz), 7.65 (3H, m), 7.38 (1H, s), 7.29 (2H, m), 7.17 (2H, m), 6.83 (1H, s), 6.51 (1H, d, J=8.4 Hz), 5.09 (1H, s), 3.89 (1H, m), 2.17 (2H, m), 2.04 (2H, m), 1.71 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 151.0, 150.4 144.4, 143.5, 143.1, 138.3, 136.6, 136.6, 135.5, 134.1, 132.2, 130.8, 130.1, 129.0, 128.2, 128.0, 127.9, 127.0, 123.6, 123.2, 113.9, 99.5, 90.5, 54.4, 31.6, 15.9.

TBI-820, 5-(3-Chlorophenyl)-3-cyclohexylimino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 7.81 (5H, m), 7.55 (2H, m), 7.11 (3H, m), 6.81 (1H, s), 6.55 (2H, m), 5.12 (1H, s), 3.94 (3H, s), 2.98 (1H, m), 1.68 (2H, m), 1.53 (3H, m), 1.28 (2H, m), 1.10 (3H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 150.3, 150.1 141.5, 138.5, 138.2, 135.3, 135.1, 134.2, 132.9, 131.0, 130.0, 129.0, 128.2, 128.0, 127.9, 127.8, 124.1, 124.0, 122.8, 117.4, 113.9, 100.1, 88.7, 56.9, 53.6, 33.0, 25.4, 23.8.

TBI-821, 5-(3-Chlorophenyl)-3-(1-methylethyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 7.84 (2H, m), 7.74 (1H, m), 7.64 (2H, m), 7.37 (1H, s), 7.17 (3H, m), 6.90 (2H, m), 6.49 (1H, m), 5.48 (1H, s), 2.38 (3H, s), 1.09 (6H, d, J=6.0 Hz). ¹³C NMR (100 MHz, CDCl₃) δ: 161.0, 155.4, 153.5, 150.9, 142.7, 142.2, 138.9, 138.6, 136.7, 134.6, 132.3, 130.1, 129.3, 128.3, 127.8, 127.2, 127.1, 124.7, 124.4, 116.8, 113.9, 96.9, 90.4, 53.7, 49.4, 23.5.

TBI-822, 5-(1-Chlorophenyl)-3-(4-tetrahydropyranyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 7.84 (2H, m), 7.74 (1H, m), 7.64 (2H, m), 7.38 (1H, s), 7.17 (3H, m), 6.90 (2H, m), 6.53 (1H, m), 5.27 (1H, s), 4.03 (3H, s), 3.96 (2H, m), 3.43 (2H, m), 2.85 (1H, m), 1.75 (4H, m). ¹³C NMR (100 MHz, CDCl₃) 161.0, 155.4, 153.5, 150.9, 142.7, 142.2, 138.9, 138.6, 136.7, 134.6, 132.3, 130.1, 129.3, 128.3, 127.8, 127.2, 127.1, 124.7, 124.4, 116.7, 113.9, 100.4, 89.1, 66.9, 53.8, 53.5, 34.2.

TBI-823, 5-(3-Chlorophenyl)-3-cyclopropylimino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 7.80 (2H, m), 7.74 (1H, m), 7.66 (2 m), 7.38 (1H, s), 7.17 (3H, m), 6.90 (2H, m), 6.44 (1H, m), 5.54 (1H, s), 4.04 (3H, s), 2.72 (1H, m), 0.84 (4H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 161.0, 155.4, 153.5, 150.9, 142.7, 142.2, 138.9, 138.6, 136.7, 134.6, 132.3, 130.1, 129.3, 128.3, 127.8, 127.2, 127.1, 124.7, 124.4, 116.8, 113.9, 100.2, 89.8, 53.7, 32.9, 10.1.

TBI-824, 5-(3-Chlorophenyl)-3-cyclobutylimino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 7.84 (2H, m), 7.69 (3H, m), 7.38 (1H, s), 7.17 (3H, m), 6.93 (2H, m), 6.50 (1H, m), 5.08 (1H, s), 4.04 (3H, s), 3.93 (1H, m), 2.20 (2H, m), 2.07 (2H, m), 1.75 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 161.0, 155.4, 153.5, 150.9, 142.7, 142.2, 138.9, 138.6, 136.7, 134.6, 132.3, 130.1, 129.3, 128.3, 127.8, 127.2, 127.1, 124.7, 124.4, 116.8, 113.9, 100.2, 90.4, 54.8, 53.7, 31.9, 16.0.

TBI-825, 5-(3-Chlorophenyl)-3-(1,3-dimethoxyisopropyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) 7.86 (2H, m), 7.64 (3H, m), 7.37 (1H, s), 7.18 (3 m), 6.91 (2H, m), 6.49 (1H, m), 5.48 (1H, s), 4.02 (3H, s), 3.72 (1H, s), 3.57 (2 m), 3.41 (2H, m), 3.30 (3H, s), 3.29 (3H, s). ¹³C NMR (100 MHz, CDCl₃) δ: 161.0, 155.4, 153.5, 150.9, 142.7, 142.2, 138.9, 138.6, 136.7, 134.6, 132.3, 130.1, 129.3, 128.3, 127.8, 127.2, 127.1, 124.7, 124.4, 116.8, 113.9, 96.9, 90.4, 74.6, 74.3, 59.2, 59.1, 58.6, 53.6.

TBI-826, 5-(3-Chlorophenyl)-3-(2,3-dimethoxy-1-propyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 7.83 (2H, m), 7.73 (1H, d, J=7.5 Hz), 7.68 (2H, m), 7.36 (1H, s), 7.19 (2H, m), 6.98 (1H, s), 6.93 (1H, dd, J=7.5, 5.1 Hz), 6.47 (1H, d, J=7.5 Hz), 5.28 (1H, s), 4.03 (3H, s), 368 (2H, m), 3.57 (1H, m), 3.48 (3H, s), 3.39 (3H, s), 3.25 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 161.0, 155.4, 153.5, 150.9, 142.7, 142.2, 138.9, 138.6, 136.7, 134.6, 132.3, 130.1, 129.3, 128.3, 127.8, 127.2, 127.1, 124.7, 124.4, 1169, 114.1, 100.2, 89.3, 81.1, 73.3, 59.3, 57.9, 53.7, 50.3.

TBI-830, 5-(4-Trifluoromethoxyphenyl)-3-(4-tetrahydropyranyl)imino-2-(pyrimidin-2-yl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 9.66 (1H, br. s), 8.55 (2H, d, J=4.8 Hz), 8.52 (1H, s), 7.78 (1H, d, J=7.8 Hz), 7.60 (2H, d, J=7.8 Hz), 7.42 (2H, d, J=7.8 Hz), 7.20 (2H, m), 6.83 (1H, t, J=4.8 Hz), 6.49 (1H, d, J=7.8 Hz), 5.16 (1H, s), 3.97 (2H, m), 3.35 (3H, m), 1.65 (4H, m).

TBI-860, 5-(4-Chlorophenyl)-3-(4-tetrahydropyranyl)imino-2-(pyrimidin-2-yl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 9.69 (1H, br. s), 8.55 (2H, d, J=4.8 Hz), 8.53 (1H, s), 7.79 (1H, d, J=7.8 Hz), 7.72 (2H, d, J=8.1 Hz), 7.31 (2H, J=8.1 Hz), 7.20 (2H, m), 6.83 (1H, t, J=4.8 Hz), 6.47 (1H, d, J=7.5 Hz), 5.24 (1H, s), 3.98 (2H, m), 3.41 (3H, m), 1.62 (4H, m).

TBI-870, 5-(2-Chlorophenyl)-3-(4-tetrahydropyranyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 9.05 (1H, br. s), 7.87 (1H, d, J=8.1 Hz), 7.79 (3H, m), 7.63 (2H, dd, J=6.0, 3.0 Hz), 7.40 (1H, dd, J=6.0, 3.0 Hz), 7.20 (2H, m), 7.00 (1H, s), 6.93 (1H, m), 6.42 (1H, d, J=8.1 Hz), 5.16 (1H, s), 4.05 (3H, s), 4.00 (2H, m), 3.48 (3H, m), 1.68 (4H, m).

TBI-871, 5-(4-Chlorophenyl)-3-(1,3-dimethoxyisopropyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 7.83 (2H, m), 7.72 (3H, m), 7.31 (2H, d, J=8.1 Hz), 7.16 (2H, m), 7.00 (1H, s), 6.92 (1H, dd, J=7.8, 4.8 Hz), 6.47 (1H, d, J=7.5 Hz), 5.49 (1H, s), 4.02 (3H, s), 3.72 (1H, m), 3.57 (2H, m), 3.39 (2 D, m), 3.26 (6H, s). ¹³C NMR (100 MHz, CDCl₃) 155.5, 153.5, 150.9, 142.7, 139.0, 135.9, 135.8, 134.7, 131.6, 131.5, 130.4, 128.7, 128.5, 128.4, 127.8, 125.0, 124.7, 123.1, 114.0, 101.7, 89.7, 74.4, 59.1, 58.7, 53.7.

TBI-872, 5-(4-Chlorophenyl)-3-(2,3-dime oxy-1-propyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 7.85 (2H, m), 7.71 (3H, m), 7.30 (2H, d, J=8.1 Hz), 7.15 (2H, m), 6.99 (1H, s), 6.93 (1H, dd, J=7.8, 4.8 Hz), 6.46 (1H, J=7.5 Hz), 5.29 (1H, s), 4.03 (3H, s), 3.68 (2H, m), 3.57 (1H, dd, J=9.9, 5.4 Hz), 3.49 (3H, s), 3.40 (3H, s), 3.28 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 155.2, 153.2, 150.9, 142.4, 138.7, 135.9, 135.8, 134.8, 131.8, 131.7, 130.2, 129.6, 129.3, 128.3, 127.9, 124.7, 124.4, 123.2, 114.1, 100.2, 89.2, 81.0, 73.3, 59.3, 57.9, 53.7, 50.4.

TBI-880, 5-(4-Chlorophenyl)-3-(4-tetrahydropyranyl)imino-2-(5-bromo-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.52 (1H, d, J=1.8 Hz), 8.37 (1H, d, J=1.5 Hz), 7.91 (1H, s), 7.74 (1H, dd, J=7.8, 1.5 Hz), 7.73 (2H, d, J=8.4 Hz), 7.30 (2H, d, J=8.4 Hz), 7.18 (2H, m), 6.90 (1H, s), 6.50 (1H, dd, J=7.8, 1.5 Hz), 5.25 (1H, s), 3.97 (2H, m), 3.41 (3H, m), 1.63 (4H, m).

TBI-881, 5-(4-Chlorophenyl)-3-(1′,4′-trans-4-methoxycyclohexyl)imino-2-(5-bromo-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.50 (1H, d, J=1.8 Hz), 8.36 (1H, d, J=1.5 Hz), 7.90 (1H, s), 7.72 (1H, dd, J=7.8, 1.5 Hz), 7.71 (2H, d, J=7.8 Hz), 7.30 (2H, d, J=7.8 Hz), 7.18 (2H, m), 6.87 (1H, s), 6.50 (1H, dd, J=7.8, 1.5 Hz), 5.27 (1H, s), 3.37 (3H, s), 3.20 (1H, m), 3.10 (1H, m), 2.07 (2H, m), 1.70 (2H, m), 1.42 (2H, m), 1.22 (2H, m).

TBI-882, 5-(4-Chlorophenyl)-3-cyclopropylimino-2-(5-bromo-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.55 (1H, s), 8.47 (1H, s), 7.88 (1H, s), 7.72 (2H, d, J=8.1 Hz), 7.70 (1H, d, J=7.5 Hz), 7.33 (2H, d, J=8.1 Hz), 7.17 (2H, m), 6.82 (1H, s), 6.44 (1H, d, J=7.5 Hz), 5.54 (1H, s), 2.74 (1H, m), 0.91 (2H, m), 0.81 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 150.9, 150.5, 144.8, 142.5, 141.5, 137.8, 135.9, 135.8, 134.8, 131.8, 131.7, 130.5, 129.5, 128.4, 128.2, 123.1, 120.6, 113.9, 99.8, 89.5, 32.9, 10.1.

TBI-883, 5-(4-Chlorophenyl)-3-cyclobutylimino-2-(5-bromo-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR 300 MHz, CDCl₃) δ: 8.52 (1H, s), 8.36 (1H, s), 7.90 (1H, s), 7.73 (2H, d, J=8.1 Hz), 7.72 (1H, d, J=7.5 Hz), 7.30 (2H, d, J=8.1 Hz), 7.20 (2H, m), 6.88 (1H, s), 6.50 (1H, d, J=7.5 Hz), 5.11 (1H, s), 3.89 (1H, m), 2.18 (2H, m), 2.05 (2H, m), 1.76 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 151.0, 150.6, 144.7, 142.7, 141.5, 138.1, 135.9, 135.8, 134.6, 131.8, 131.7, 130.3, 129.4, 128.5, 128.2, 123.4, 120.6, 114.1, 100.5, 90.5, 54.6, 31.9, 16.0.

TBI-890, 5-(2-Chlorophenyl)-3-(1-methylethyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.58 (1H, d, J=2.3 Hz), 8.32 (1H, d, J=4.8 Hz), 8.10 (1H, s), 7.78 (2H, m), 7.72 (1H, d, J=7.5 Hz), 7.62 (2H, m), 7.40 (1H, m), 7.29 (1H, m), 7.15 (2H, m), 6.85 (1H, s), 6.42 (1H, d, J=7.5 Hz), 5.16 (1H, s), 3.46 (1H, m), 1.08 (6H, d, J=6.0 Hz). ¹³C NMR (100 MHz, CDCl₃) δ: 151.0, 150.7, 144.1, 143.8, 143.6, 136.8, 135.6, 134.6, 133.5, 133.4, 131.8, 131.2, 130.7, 130.5, 129.4, 128.4, 128.0, 127.9, 123.6, 123.1, 113.4, 99.7, 89.1, 49.5, 23.7.

TBI-891, 5-(2-Chlorophenyl)-3-cyclohexylimino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.58 (1H, d, J=2.3 Hz), 8.32 (1H, d, J=4.7 Hz), 7.78 (2H, m), 7.72 (1H, dd, J=7.8, 2.5 Hz), 7.62 (2H, m), 7.40 (1H, m), 7.29 (1H, m), 7.18 (2H, m), 6.85 (1H, s), 6.42 (1H, dd, J=7.8, 2.5 Hz), 5.16 (1H, s), 3.06 (1H, m), 1.71 (2H, m), 1.61 (3H, m), 1.43 (2H, m), 1.22 (3H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 151.0, 150.7, 144.1, 143.8, 143.6, 136.8, 135.6, 134.6, 133.5, 133.4, 131.7, 131.2, 130.7, 130.5, 129.4, 128.4, 128.0, 127.9, 123.6, 123.1, 113.4, 99.7, 89.1, 57.9, 33.7, 25.7, 24.7.

TBI-892, 5-(2-Chlorophenyl)-3-cyclopropylimino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.56 (1H, d, J=2.3 Hz), 8.31 (1H, d, J=4.7 Hz), 7.79 (2H, m), 7.74 (1H, dd, J=7.8, 2.5 Hz), 7.61 (2H, m), 7.42 (1H, m), 7.30 (1H, m), 7.18 (2H, m), 6.85 (1H, s), 6.42 (1H, dd, J=7.8, 2.5 Hz), 5.16 (1H, s), 2.74 (1H, m), 0.83 (2H, mL 0.78 (2H, m).

TBI-678, 5-(4-Trifluoromethyl phenyl)-3-(1-methylethyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.64 (brs, 1H), 8.61 (d, J=2.4 Hz, 1H), 8.34˜8.32 (dd, J=4.5, 1.2 Hz, 1H), 8.20 (d, 8.4 Hz, 2H), 7.89˜7.88 (m, 1H), 7.84 (d, J=8.4 Hz, 2H), 7.66˜7.63 (m, 1H), 7.47˜7.43 (dd, J=8.1, 4.5 Hz, 1H), 7.24˜7.21 (m, 2H), 6.67 (s, 1H), 6.43˜6.40 (m, 1H), 5.15 (s, 1H), 3.39˜3.31 (m, 1H), 1.04 (d, J=6.0 Hz, 6H). ¹³C NMR (100 MHz, CDCl₃) δ: 150.9, 150.2, 144.4, 144.0, 143.7, 140.8, 136.7, 135.6, 134.6, 131.2, 129.9, 128.6, 128.5, 128.4, 128.0, 127.8, 123.6, 123.2, 113.7, 99.4, 89.1, 49.4, 23.5. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₃F₃N₅: 474.19055; found: 474.1906.

TBI-679, 5-(4-Fluorophenyl)-3-(1-methylethyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, DMSO-d₆) δ: 8.61 (d, J=2.1 Hz, 1H), 8.32 (d, J=4.5 Hz, 1H), 7.88˜7.85 (m, 1H), 7.65˜7.63 (m, 5H), 7.47˜7.43 (dd, J=8.1, 4.2 Hz, 1H), 7.25 (br. 2H), 6.70 (s, 1H), 6.51 (br, 1H), 5.23 (s, 1H), 3.42˜3.38 (m, 1H), 1.07 (d, J=6.3 Hz, 6H). ¹³C NMR (100 MHz, CDCl₃) δ: 162.9 (d, J=250.0 Hz), 150.9, 150.4, 144.3, 144.0, 143.7, 136.8, 135.6, 135.2, 133.5, 131.7, 130.9, 130.8, 128.3, 127.9, 127.7, 123.6, 123.0, 118.5 (d, J=22.7 Hz), 113.9, 99.4, 89.1, 49.4, 23.5. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₆H₂₃FN₅: 424.1937; found: 424.1938.

TBI-680, 5-(4-Fluorophenyl)-3-(2-morpholinoethyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.58 (s, 1H), 8.34 (d, J=4.5 Hz, 1H), 7.78˜7.71 (m, 2H), 7.45˜7.40 (m, 2H), 7.35˜7.31 (m, 3H), 7.21˜7.14 (m, 2H), 6.86 (s, 1H), 6.48 (d, J=7.5, 1H), 5.27 (s, 1H), 3.71 (t, J=4.5 Hz, 4H), 3.34 (t, J=7.5 Hz, 2H), 2.71 (t, J=7.5 Hz, 2H), 2.48 (br, 4H). ¹³C NMR (100 MHz, CDCl₃) δ: 162.9 (d, J=250.0 Hz) 152.8, 150.7, 144.5, 144.0, 143.4, 136.7, 135.7, 135.2, 1313, 131.6, 130.7, 130.7, 128.5, 128.0, 123.7, 123.2, 118.7 (d, J=22.6 Hz), 114.1, 99.5, 89.0, 66.9, 59.9, 54.1, 47.9. HRMS (ESI-TOF^3-): m/z [M+H]⁺ calcd for C₂₉H₂₈FN₆O: 495.2308; found: 495.2307.

TBI-681, 5-(4-Fluorophenyl)-3-(4-tetrahydropyranyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, DMSO-d₆) δ: 8.66 (brs, 1H), 8.62 (d, J=2.4 Hz, 1H), 8.34˜8.32 (dd, J=4.8, J=1.2, 1H), 7.90˜7.86 (m, 1H), 7.68˜7.62 (m, 5H), 7.48=7.44 (m, 1H), 7.28˜7.20 (m, 2H), 6.68 (s, 1H), 6.52˜6.49 (m, 1H), 5.19 (s, 1H), 3.90˜3.86 (m, 2H), 3.30˜3.24 (m, 3H), 1.58˜1,48 (m, 4H). ¹³C NMR (100 MHz, CDCl₃) δ: 162.9 (d, J=250.0 Hz) 151.1, 150.7, 144.5, 144.0, 143.6, 136.6, 135.7, 135.3, 133.4, 131.6, 130.8, 130.7, 128.4, 128.0, 127.9, 123.7, 123.1, 118.5 (d, J=22.7 Hz), 114.0, 99.6, 88.9, 66.1, 54.3, 33.4. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₅FN₅O: 466.2043; found: 466.2042.

TBI-682, 5-(4-Fluorophenyl)-3-(N-methyl-4-piperidyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.60 (br, 1H), 8.34 (d, J=4.5 Hz, 1H), 7.78 (d, J=8.7 Hz, 1H), 7.71 (d, J=7.5 Hz, 1H), 7.47˜7.42 (m, 2H), 7.37˜7.27 (m, 3H), 7.22˜7.13 (m, 2H), 6.86 (s, 1H), 6.50 (d, J=7.5 Hz, 1H), 5.21 (s, 1H), 3.15˜3.11 (m, 1H), 2.81˜2.77 (m, 2H), 2.30 (s, 3H), 2.05 (br, 2H), 1.68 (br, 4H). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, J=249.3 Hz) 151.0, 150.8, 144.4, 144.0, 143.5, 136.7, 135.7, 135.2, 133.4, 131.6, 130.8, 130.7, 128.4, 128.0, 127.9, 123.6, 123.1, 118.4 (d, J=22.6 Hz), 114.0, 99.5, 89.0, 54.0, 46.4, 32.7. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₈FN₆: 479.2359: found: 479.2358.

TBI-683, 5-(4-Fluorophenyl)-3-(N-isobutyl-4-piperidyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.58 (d, J=1.8 Hz, 1H), 8.34 (d, J=3.9 Hz, 1H), 7.78 (d, J=7.8, 1H), 7.70 (d, J=7.5 Hz, 1H), 7.46˜7.41 (m, 2H), 7.36˜7.26 (m, 3H), 7.21˜7.12 (m, 2H), 6.85 (s, 1H), 6.49 (d, J=7.5 Hz, 1H), 5.25 (s, 1H), 3.13˜3.11 (m, 1H), 2.80˜2.77 (m, 2H), 2.06 (d, J=7.2 Hz, 2H), 1.96˜1.81 (m, 2H), 1.81˜1.62 (m, 5H), 0.90 (d, J=6.6 Hz, 6H). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, J=248.9 Hz), 151.0, 150.9, 144.3, 143.9, 143.6, 136.8, 135.7, 135.1, 133.4, 131.7, 130.9, 130.8, 128.4, 127.8, 123.6, 123.0, 118.4 (d, J=22.7 Hz), 114.0, 99.5, 89.1, 67.1, 56.0, 52.5, 32.8, 25.7, 21.0. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₂H₃₄FN₆: 521.2828; found: 521.2819.

TBI-684, 5-(4-Fluorophenyl)-3-(N-cyclopentyl-4-piperidyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.58 (d, J=2.7 Hz, 1H), 8.35˜8.33 (dd, J=4.8, 1.2 Hz, 1H), 7.79˜7.76 (m, 1H), 7.72˜7.69 (m, 1H), 7.47˜7.41 (m, 2H), 7.36˜7.28 (m, 3H), 7.21˜7.12 (m, 2H), 6.50˜6.47 (m, 1H), 6.85 (s, 1H), 5.25 (s, 1H), 3.15 (m, 1H), 2.95˜2.91 (m, 2H), 2.49˜2.44 (m, 1H), 2.05 (br, 2H), 1.87 (br, 2H), 1.67 (br, 6H), 1.58˜1.54 (m, 2H), 1.41 (br. 2H). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, J=248.9 Hz), 150.9, 144.3, 143.9, 143.6, 136.8, 135.7, 135.2, 133.4, 131.7, 130.9, 130.8, 128.4, 127.8, 123.6, 123.0, 118.4 (d, J=22.7 Hz), 113.9, 99.5, 89.0, 67.7, 55.5, 50.9, 32.8, 30.7, 24.2. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₃H₃₄FN₆: 533.28289; found: 533.2827.

TBI-685, 5-(4-Fluorophenyl)-3-(4-methoxycyclohexyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.58 (d, J=14, 1H), 8.33 (d, J=3.9 Hz, 1H), 7.80˜7.45 (m, 2H), 7.42˜7.39 (m, 2H), 7.35˜7.28 (m, 1H), 7.21˜7.13 (m, 4H), 6.85 (s, 1H), 6.51˜6.48 (m, 1H), 5.25 (s, 1H), 3.37 (s, 3H), 3.23˜3.15 (m, 1H), 3.12˜3.06 (m, 1H), 2.10˜2.05 (m, 2H), 1.72˜1.68 (m, 2H), 1.49˜1.37 (m, 2H), 1.26˜1.12 (m, 2H). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, J=250.1 Hz), 151.2, 150.9, 144.3, 143.9, 143.6, 136.7, 135.6, 135.1, 133.3, 131.7, 130.8, 130.7, 128.4, 127.9, 123.6, 123.0, 118.4 (d, J=22.7 Hz), 114.0, 99.5, 89.1, 78.4, 57.4, 55.8, 31.1, 30.0. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₂₉FN₅O: 494.23561; found: 494.2355

TBI-686, 5-(4-Trifluoromethylphenyl)-3-(4-tetrahydropyranyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.61 (d, J=2.4 Hz, 1H), 8.36 (d, J=4.2 Hz, 1H), 8.04 (d, J=8.4 Hz, 2H), 7.79=7.72 (m, 2H), 7.53 (d, J=8.4 Hz, 2H), 7.34˜7.29 (dd, J=8.1, 4.5 Hz, 1H), 7.25˜7.14 (m, 2H), 6.87 (s, 1H), 6.46 (d, J=8.1 Hz, 1H), 5.16 (s, 1H), 3.99˜3.94 (m, 2H), 3.41˜3.28 (m, 3H), 1.73˜1.57 (m, 4H), ¹³C NMR (100 MHz, CDCl₃) δ: 151.0, 150.6, 144.6, 144.0, 143.6, 140.8, 136.5, 135.6, 134.8, 130.9, 129.8, 128.6, 128.1, 128.0, 123.7, 123.4, 113.8, 99.6, 89.0, 66.1, 54.5, 33.4. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₅F₃N₅O: 516.20112; found: 516.2011.

TBI-687, 5-(4-Trifluoromethylphenyl)-3-(N-isobutyl-4-piperidyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.59 (d, J=2.4 Hz, 1H), 8.34 (d, J=3.9 Hz, 1H), 8.03 (d, J=8.7 Hz, 2H), 7.77 (d, J=8.7 Hz, 1H), 7.72 (d, J=7.5 Hz, 1H), 7.52 (d, J=8.4 Hz, 2H), 7.33˜7.29 (dd, J=8.4, 4.5 Hz, 1H), 7.23˜7.13 (m, 2H), 6.85 (s, 1H), 6.45 (d, J=7.5 Hz, 1H), 5.15 (s, 1H), 3.09=3.05 (m, 1H), 2.80˜2.76 (m, 2H), 2.06 (d, J=7.2 Hz, 2H), 1.93˜1.86 (m, 2H), 1.81˜1.54 (m, 5H), 0.89 (d, J=6.6 Hz, 6 1˜1). ¹³C NMR (100 MHz, CDCl₃) δ: 150.9, 144.4, 144.0, 143.6, 140.9, 136.7, 135.6, 134.7, 131.0, 129.9, 128.6, 128.5, 128.0, 127.9, 123.7, 123.3, 113.7, 99.5, 89.3, 67.0, 56.1, 52.3, 32.7, 25.7, 21.0. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₃H₃₄F₃N₆: 571.2797; found: 571.2799.

TBI-688, 5-(4-Trifluoromethylphenyl)-3-(4-methoxycyclohexyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.58 (d, J=2.7 Hz, 1H), 8.34 (d, J=4.8 Hz, 1H), 8.02 (d, J=8.1 Hz, 2H), 7.78 (d, J=8.4 Hz, 1H), 7.73˜170 (dd, J=7.5, 1.2 Hz, 1H), 7.52 (d, J=8.1 Hz, 2H), 7.33˜7.28 (dd, J=8.4, 4.8 Hz, 1H), 7.23˜7.13 (m, 2H), 6.85 (s, 1H), 6.43 (d, J=7.5 Hz, 1H), 5.18 (s, 1H), 3.22˜3.15 (m, 1H), 3.09˜3.03 (m, 1H), 2.07˜2.04 (m, 2H), 1.70˜1.66 (m, 2H), 1.47˜1.35 (m, 2H), 1.21˜1.09 (m, 2H). ¹³C NMR (100 MHz, CDCl₃) δ: 151.0, 150.9, 144.5, 144.0, 143.6, 140.8, 136.7, 135.6, 134.7, 131.1, 129.8, 128.57, 128.53, 128.51, 128.0, 127.9, 123.7, 123.3, 113.8, 99.6, 89.2, 78.4, 57.3, 55.8, 31.1, 29.8. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₂₉F₃N₅O: 544.2324; found: 544.2328.

TBI-689, 5-(4-Trifluoromethylphenyl)-3-(N-methyl-4-piperidyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.60 (d, J=2.7 Hz, 1H), 8.36˜8.34 (m, 1H), 8.04 (d, J=8.4 Hz, 2H), 7.78 (d, J=8.4 Hz, 1H), 7.74˜7.71 (dd, J=7.5, 1.5 Hz, 1H), 7.53 (d, J=8.4 Hz, 2H), 7.33˜7.29 (dd, J=8.4, 4.8 Hz, 1H), 7.24˜7.14 (m, 2H), 6.85 (s, 1H), 6.46 (d, J=8.1 Hz, 1H), 5.14 (s, 1H), 3.06˜3.04 (m, 1H), 2.80˜2.76 (m, 2H), 2.26 (s, 3H), 1.97˜1.93 (m, 2H), 1.73˜1.62 (m, 4H). ¹³C NMR (100 MHz, CDCl₃) δ: 151.0, 150.8, 144.5, 144.1, 143.6, 140.9. 136.6, 135.6, 134.7, 131.2, 129.9, 128.6, 128.5, 128.4, 128.0, 127.8, 123.6, 123.2, 113.7, 99.5, 89.3, 58.4, 55.4, 54.1, 46.4, 32.8, 18.5. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₂₈F₃N₆: 529.2327; found: 529.2326.

TBI-690, 5-(4-Trifluoromethylphenyl)-3-(2-morpholinoethyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.59 (d, J=14 Hz, 1H), 8.35 (d, J=4.5 Hz, 1H), 2.47 (t, J=4.5 Hz, 4H), 8.03 (d, J=8.4 Hz, 2H), 7.79˜7.73 (m, 2H) 7.52 (d, J=8.4 Hz, 2H), 2.70 (t, J=7.5 Hz, 2H), 7.34˜7.29 (dd, J=8.1, 4.5 Hz, 1H), 7.27˜7.14 (m, 2H), 6.87 (s, 1H), 6.40 (d, J=8.1 Hz, 1H), 5.23 (s, 1H), 3.70 (t, J=4.8 Hz, 4H), 3.34 (t, J=7.5 Hz, 2H). ¹³C NMR (100 MHz, CDCl₃) δ: 152.7, 150.7, 144.6, 144.0, 143.4, 140.7, 136.6, 135.7, 134.7, 131.0, 129.8, 128.8, 128.6, 128.1, 123.7, 123.5, 113.9, 99.6, 89.0, 66.9, 59.7, 54.1, 48.0. HR-MS/TOF: [M+H]⁺:545.2280. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₂₈F₃N₆O: 545.2276; found: 545.2280.

TBI-691, 5-(4-Trifluoromethylphenyl)-3-(N-cyclopentyl-4-piperidyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.59 (br, 1H), 8.35 (d, J=3.9 Hz, 1H) 8.04 (d, J=8.1 Hz, 2H), 7.77 (d, J=8.1 Hz, 1H), 7.73 (d, J=7.8 Hz, 1H), 7.53 (d, J=8.1 Hz, 2H), 7.34˜7.29 (m, 1H), 7.24˜7.14 (m, 2H), 6.86 (s, 1H), 6.46 (d, J=8.1 Hz, 1H) 5.15 (s, 1H) 3.09 (br, 1H), 2.96˜2.92 (br, 2H), 2.47 (br, 1H), 2.00 (br, 2H), 1.85 (br, 2H), 1.67˜1.57 (br, 8H), 1.42 (br, 2H). ¹³C NMR (100 MHz, CDCl₃) δ: 150.9, 144.5, 144.0, 143.6, 140.8, 136.6, 135.6, 134.7, 131.0, 129.9, 128.5, 128.0, 123.7, 123.3, 113.7, 99.5, 89.3, 67.6, 50.7, 32.6, 30.5, 24.2. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₄H₃₄F₃N₆: 583.2797; found: 583.2797.

TBI-692, 5-(4-Fluorophenyl)-3-(1-methylethyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.45 (d, J=2.4 Hz, 1H ), 7.70˜7.67 (m, 2H), 7.45˜7.39 (m, 2H), 7.35˜7.31 (m, 2H), 7.19˜7.10 (m, 3H), 6.71 (s, 1H), 6.47˜6.44 (dd, J=8.1, 1.5 Hz, 1H), 5.27 (s, 1H), 3.50˜3.41 (m, 1H), 2.56 (s, 3H), 1.10 (d, J=6.3 Hz, 6H). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, J=248.5 Hz), 153.3, 151.0, 150.5, 144.4, 143.7, 135.6, 135.1, 134.1, 133.5, 131.7, 130.9, 130.8, 129.4, 128.2, 127.5, 123.1, 122.9, 118.4 (d, J=22.7 Hz), 113.9, 98.8, 89.0, 49.4, 23.8, 23.5. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₅FN₅: 438.2088; found: 438.2090.

TBI-693, 5-(4-Fluorophenyl)-3-(1-methylethyl)imino-2-(2-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.28 (d, J=4.2 Hz, 1H), 7.81 (d, J=8.1 Hz, 1H), 7.67 (d, 7.2 Hz, 1H), 7.45˜7.40 (m, 2H), 7.36˜7.31 (m, 2H), 7.20˜7.10 (m, 3H), 6.58 (s, 1H), 6.46 (d, J=7.8 Hz, 1H), 5.27 (s, 1H), 3.51˜3.43 (m, 1H), 2.55 (s, 3H), 1.10 (d, J=6.3 Hz, 6H). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, J=248.9 Hz), 152.2, 151.0, 150.4, 144.2, 135.6, 135.1, 134.8, 133.5, 131.7, 130.9, 130.8, 129.1, 128.2, 127.5, 122.9, 121.6, 118.5 (d, J=23.1 Hz), 113.9, 98.8, 89.0, 49.3, 23.6, 20.9. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₅FN₅: 438.2088: found: 438.2094.

TBI-694, 5-(4-Trifluoromethylphenyl)-3-ethylethyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.46 (d, J=2.4 Hz, 1H), 8.02 (d, J=7.8 Hz, 2H), 7.69 (d, J=7.8, 2 Hz, 2H), 7.52 (d, J=8.1 Hz, 2H), 7.21˜7.09 (m, 3H), 6.72 (s, 1H), 6.38 (d, J=8.4 Hz, 1H), 5.22 (s, 1H), 3.45˜3.41 (m, 1H), 2.56 (s, 3H), 1.09 (d, J=6.0 Hz, 6H). ¹³C NMR (100 MHz, CDCl₃) δ: 153.5, 151.0, 150.3, 144.5, 143.8, 140.9, 135.6, 134.6, 131.1, 129.9, 129.5, 128.6, 128.3, 127.6, 123.2, 123.1, 113.6, 98.8, 89.1, 49.4, 23.8, 23.5. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₅F₃N₅: 488.2062; found: 488.2063.

TBI-695, 5-(4-Trifluoromethylphenyl)-3-(4-methoxycyclohexyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H, NMR (300 MHz, CDCl₃) δ: 8.44 (d, J=2.1 Hz, 1H), 8.02 (d, J=8.1 Hz, 2H), 7.71˜7.69 (m, 2H), 7.52 (d, J=8.1 Hz, 2H), 7.22˜7.12 (m, 3H), 6.72 (s, 1H), 6.42 (d, J=8.1 Hz, 1H), 5.17 (s, 1H), 3.35 (s, 3H), 3.22˜3.02 (m, 2H), 2.56 (s, 3H), 2.07˜2.04 (m, 2H), 1.69˜1.66 (m, 2H), 1.46˜1.08 (m, 4H). ¹³C NMR (100 MHz, CDCl₃) δ: 153.5, 151.0, 150.8, 144.3, 143.8, 140.8, 135.6, 134.6, 133.9, 131.0, 129.8, 129.5, 128.5, 128.4, 127.7, 123.2, 113.7, 98.9, 89.2, 78.4, 57.3, 55.8, 31.1, 30.6, 30.0, 29.8, 23.8. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₂H₃₁F₃N₅O: 558.5469; found: 558.2471.

TBI-696, 5-(4-Trifluoromethylphenyl)-3-(4-tetrahydropyranyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.47 (d, J=2.1 Hz, 1H), 8.03 (d, J=8.4 Hz, 2H), 7.73˜7.66 (m, 2H), 7.52 (d, J=8.4 Hz, 2H), 7.24˜7.13 (m, 3H), 6.74 (s, 1H), 6.45 (d, 8.1 Hz, 1H), 5.15 (s, 1H), 3.99˜3.95 (m, 2H), 3.39˜3.29 (m, 3H), 2.57 (s, 3H), 1.69˜1.57 (m, 4H). ¹³C NMR (100 MHz, CDCl₃) δ: 153.7, 151.1, 150.7, 144.4, 143.9, 140.9, 135.6, 134.7, 133.8, 130.9, 129.8, 129.6, 128.5, 127.8, 123.3, 123.2, 113.7, 99.0, 89.0, 66.5, 66.1, 54.6, 33.4, 32.5, 23.9. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₂₇F₃N₅O: 530.21677: found: 530.2167.

TBI-697, 5-(4-Trifluoromethylphenyl)-3-(N-methyl-4-piperidyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.47 (d, J=2.7 Hz, 1H), 8.03 (d, J=8.4 Hz, 2H), 7.71˜7.65 (m, 2H), 7.52 (d, J=8.4 Hz, 2H), 7.22˜7.12 (m, 3H), 6.72 (s, 1H), 6.45 (d, J=7.5 Hz, 1H), 5.12 (s, 1H), 3.05 (br, 1H), 2.80˜2.76 (m, 2H), 2.56 (s, 3H) 2.26 (s, 3H), 1.94 (br, 2H), 1.73˜1.62 (m, 4H). ¹³C NMR (100 MHz, CDCl₃) δ: 153.6, 151.1, 150.8, 144.4, 143.9, 140.9, 135.6, 134.6, 133.9, 130.9, 129.9, 129.6, 128.5, 127.7, 123.2, 113.7, 98.9, 89.2, 55.2, 54.0, 46.3, 32.7, 23.8. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₀F₃N₆: 543.2484; found: 543.2484.

TBI-698, 5-(4-Trifluoromethylphenyl)-3-(2-morpholinoethyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.46 (br, 1H), 8.03 (d, J=8.4 Hz, 2H), 7,70˜7.67 (m, 2H), 7.52 (d, J=8.1 Hz, 2H), 7.20˜7.17 (m, 3H), 6.75 (s, 1H), 6.41 (br, 1H), 5.22 (s, 1H), 3.70 (t, J=4.5 Hz, 4H), 3.34 (t, J=7.2 Hz, 2H), 2.70 (t, J=7.2 Hz, 2H), 2.57 (s, 3H), 2.47 (t, J=4.5 Hz, 4H). ¹³C NMR (100 MHz, CDCl₃) δ: 153.7, 152.8, 150.6, 143.9, 140.7, 135.6, 134.7, 133.8, 130.9, 129.7, 128.7, 127.9, 123.3, 113.9, 98.9, 89.0, 66.9, 59.7, 54.1, 47.9, 23.9. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₀F₃N₆O: 559.2433; found: 559.2433.

TBI-699, 5-(4-Trifluoromethylphenyl)-3-(1-methylethyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.92 (br, 1H), 8.02 (d, J=8.1 Hz, 2H), 7.86˜7.81 (m, 2H), 7.70 (d, J=8.4 Hz, 1H), 7.52 (d, J=8.4 Hz, 2H), 7.21˜7.09 (m, 2H), 6.94˜6.90 (m, 2H), 6.37 (d, J=8.1 Hz, 1H), 5.22 (s, 1H), 4.04 (s, 3H), 3.47˜3.38 (m, 1H), 1.09 (d, J=6.3 Hz, 6H). ¹³C NMR (100 MHz, CDCl₃) δ: 155.5, 151.2, 150.5, 142.9, 140.9, 138.9, 131.3, 129.9, 128.6, 128.3, 127.7, 125.0, 124.8, 123.0, 116.8, 113.6, 100.1, 89.3, 53.7, 49.4, 23.5. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₅F₃N₅O: 504.2011: found: 504.2013.

TBI-700, 5-(4-Trifluoromethylphenyl)-3-(4-methoxycyclohexyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.95 (br, 1H), 8.02 (d, J=8.1 Hz, 2H), 7.86˜7.81 (m, 2H), 7.73˜7.70 (dd, J=7.5, 1.5 Hz, 1H), 7.52 (d, J=7.8 Hz, 2H), 7.22˜7.11 (m, 2H), 7.06˜6.90 (m, 2H), 6.41 (d, J=8.1 Hz, 1H), 5.18 (s, 1H), 4.03 (s, 3H), 3.35 (s, 3H), 3.28˜3.20 (m, 1H), 3.13˜3.06 (m, 1H), 2.07˜2.03 (m, 2H), 1.72˜1.68 (m, 2H), 1,49˜1.36 (m, 2H), 1.25˜1.15 (m, 2H). ¹³C NMR (100 MHz, CDCl₃) δ: 155.4, 151.1, 142.8, 140.8, 138.8, 135.6, 134.6, 131.2, 129.9, 128.5, 128.4, 127.8, 124.8, 124.7, 123.1, 116.8, 113.7, 100.2, 89.3, 78.2, 56.8, 55.7, 53.7, 30.7, 29.3. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₂H₃₁F₃N₅O₂: 574.2429; found: 574.2432.

TBI-701, 5-(4-Trifluoromethylphenyl)-3-(4-tetrahydropyranyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 9.04 (brs, 1H), 8.03 (d, J=8.4 Hz, 2H), 7.87˜7.82 (m, 2H), 7.75˜7.72 (dd, J=8.1, 1.5 Hz, 1H), 7.43 (d, J=8.4 Hz, 2H), 7.24˜7.13 (m, 2H), 6.98 (s, 1H), 6.95˜6.91 (dd, J=7.5, 4.8 Hz, 1H), 6.43 (d, J=7.8 Hz, 1H), 5.16 (s, 1H), 4.04 (s, 3H), 4.02˜3.95 (m, 2H), 3.49˜3.37 (m, 3H), 1.66˜1.59 (m, 4H). ¹³C NMR (100 MHz, CDCl₃) δ: 155.3, 151.1, 150.9, 142.7, 140.8, 138.9, 135.6, 134.8, 131.6, 129.9, 128.5, 128.4, 127.9, 124.8, 124.5, 123.3, 116.8, 113.7, 100.3, 89.1, 65.6, 53.8, 53.6, 33.3. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₂₇F₃N₅O₂: 546.2116; found: 546.2126.

TBI-702, 5-(4-Trifluoromethylphenyl)-3-(N-isobutyl-4-piperidyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 9.03 (brs, 1H), 8.02 (d, J=8.1 Hz, 2H), 7.86˜7.81 (m, 2H), 7.72 (d, J=7.2 Hz, 1H), 7.52 (d, J=8.1 Hz, 2H), 7.22˜7.12 (m, 2H), 6.95˜6.90 (m, 2H), 6.43 (d, J=8.) Hz, 1H), 5.16 (s, 1H), 4.04 (s, 3H), 3.11 (br, 1H), 2.74 (br, 2H), 2.07˜1.96 (m, 4H), 1.80˜1.63 (m, 5H), 0.90 (d, J=6.6 Hz, 6H). ¹³C NMR (100 MHz, CDCl₃) δ: 155.3, 150.9, 142.7, 140.9, 138.7, 135.6, 134.7, 131.1, 129.9, 128.5, 128.4, 127.8, 124.8, 124.4, 123.2, 116.8, 113.7, 100.2, 89.3, 67.3, 55.4, 53.7, 52.0, 32.7, 25.6, 21.1. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₄H₃₆F₃N₆O: 601.2902; found: 601.2908.

TBI-703, 5-(4-Trifluoromethylphenyl)-3-(N-methyl-4-piperidyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 9.08 (brs, 1H), 8.03 (d, J=8.4 Hz, 2H), 7.86˜7.80 (m, 2H), 7.74˜7.71 (m, 1H), 7.52 (d, J=8.4 Hz, 2H), 7.23˜7.12 (m, 2H), 6.96 (s, 1H), 6.49˜6.90 (dd, J=7.8, 4.8 Hz, 1H) 6.42 (d, J=7.5 Hz, 1H), 5.16 (s, 1H), 4.03 (s, 3H), 3.15 (br, 1H), 2.79˜2.75 (m, 2H), 2.30 (s, 3H), 2.07 (br, 2H), 1.68˜1.67 (m, 4H). ¹³C NMR (100 MHz, CDCl₃) δ: 155.3, 151.0, 150.9, 142.6, 140.8, 138.7, 135.6, 134.7, 131.1, 129.9, 128.5, 128.4, 127.8, 124.8, 124.3, 123.2, 116.8, 113.7, 100.2, 89.2, 53.7, 53.4, 46.4, 32.5. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₀F₃N₆O: 559.2433; found: 559.2437.

TBI-704, 5-(4-Trifluoromethylphenyl)-3-(2-morpholinoethyl)imino-2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.82 (brs, 1H), 8.02 (d, J=8.1 Hz, 2H), 7.87˜7.82 (m, 2H), 7.74 (d, J=7.8 Hz, 1H), 7.52 (d, J=8.1 Hz, 2H), 7.24˜7.13 (m, 2H), 6.97 (s, 1H), 6.95˜6.91 (dd, J=7.2, 4.8 Hz, 1H), 6.39 (d, J=7.8 Hz, 1H), 5.21 (s, 1H), 4.04 (s, 3H), 3.70 (t, J=4.5 Hz, 4H), 3.34 (t, J=6.6 Hz, 2H), 2.74 (t, J=6.6 Hz, 2H), 2.53 (t, J=4.2 Hz, 4H). ¹³C NMR (100 MHz, CDCl₃) δ: 155.3, 152.8, 150.9, 142.5, 140.8, 139.0, 135.6, 134.6, 131.1, 129.8, 128.7, 128.7, 128.4, 127.9, 124.8, 124.6, 123.3, 116.8, 113.8, 100.1, 89.2, 67.0, 59.7, 54.2, 53.7, 48.5. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₀F₃N₆O₂: 575.2382; found: 575.2385.

TBI-705, 5-(4-Trifluoromethylphenyl)-3-(1-methylethyl)imino-2-(2-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.29 (d, J=3.6 Hz, 1H), 8.02 (d, J=8.1 Hz, 2H), 7.81 (d, J=7.2 Hz, 2H), 7.70˜7.67 (m, 1H), 7.52 (d, J=8.4 Hz, 2H), 7.21˜7.10 (m, 3H), 6.58 (s, 1H), 6.39˜6.37 (m, 1H), 5.23 (s, 1H), 3.49˜3.41 (m, 1H), 2.56 (s, 3H), 1.09 (d, J=6.0 Hz, 6H), ¹³C NMR (100 MHz, CDCl₃) δ: 152.3, 151.0, 150.2, 144.3, 144.2, 140.9, 135.5, 134.7, 131.1, 129.9, 129.3, 128.5, 128.3, 127.6, 123.1, 121.7, 113.7, 98.8, 89.1, 49.3, 23.6, 20.9. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₅F₃N₅: 488.2062: found: 488.2060.

TBI-706, 5-(4-Trifluoromethylphenyl)-3-(4-methoxycyclohexyl)imino-2-(2-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.29 (d, J=4.2 Hz, 1H), 8.02 (d, J=8.1 Hz, 2H), 7.82 (d, J=7.8 Hz, 2H), 7.70 (d, J=7.8 Hz, 1H), 7.52 (d, J=8.4 Hz, 2H), 7.22˜7.12 (m, 3H), 6.60 (s, 1H), 6.42 (d, J=7.8, 1H), 5.17 (s, 1H), 3.35 (s, 3H), 3.24˜3.06 (m, 2H), 2.54 (s, 3H), 2.06˜2.03 (m, 2H), 1.72˜1.68 (m, 2H), 1.47˜1.13 (m, 4H), ¹³C NMR (100 MHz, CDCl₃) δ: 152.2, 150.9, 150.8, 144.2, 144.0, 140.8, 135.6, 134.7, 134.6, 131.0, 129.8, 129.1, 128.5, 128.4, 127.8, 123.2, 121.7, 113.7, 99.0, 89.1, 78.2, 56.9, 55.8, 31.0, 29.9, 29.5, 20.9. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₂H₃₁F₃N₅O: 558.5480; found: 558.2479.

TBI-707, 5-(4-Trifluoromethylphenyl)-3-(4-tetrahydropyranyl)imino-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.30 (d, J=4.2 Hz, 1H), 8.04 (d, J=8.4 Hz, 2H), 7.82 (d, J=8.1 Hz, 1H), 7.71 (d, J=7.2 Hz, 1H) 7.53 (d, J=8.4 Hz, 2H), 7.24˜7.14 (m, 3H), 6.63 (s, 1H), 6.45 (d, J=7.8 Hz, 1H), 5.18 (s, 1H), 4.00˜3.94 (m, 2H), 3.46˜3.34 (m, 3H), 2.55 (s, 3H), 1.67˜1.63 (m, 4H). ¹³C NMR (100 MHz, CDCl₃) δ: 152.4, 151.2, 150.9, 144.6, 144.3, 141.0, 135.8, 135.0, 134.7, 131.1, 130.1, 129.4, 128.8, 128.7, 128.1, 123.6, 121.9, 114.0, 99.3, 89.2, 66.1, 54.2, 33.6, 21.2. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₂₇F₃N₅O: 530.2167; found: 530.2165.

TBI-708, 5-(4-Trifluoromethylphenyl)-cyclohexylimino-2-(2-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.28˜8.27 (m, 1H), 8.03 (d, J=8.1 Hz, 2H), 7.83˜7.80 (m, 1H), 7.70˜7.67 (dd, J=7.5, 1.2 Hz, 1H), 7.53 (d, J=8.4 Hz, 2H), 7.21˜7.10 (m, 3H), 6.60 (s, 1H), 6.45˜6.42 (dd, J=7.8, 1.2 Hz, 1H), 5.17 (s, 1H), 3.11=3.04 (m, 1H), 2.55 (s, 3H), 1.75˜1.71 (m, 2H), 1.60˜1.57 (m, 3H), 1.43˜1.11 (m, 5H). ¹³C NMR (100 MHz, CDCl₃) δ: 152.1, 151.0, 150.4, 144.2, 140.9, 135.6, 134.7, 134.6, 131.0, 129.9, 129.0, 128.5, 128.3, 127.6, 123.1, 121.7, 113.6, 98.8, 89.4, 57.6, 33.6, 25.8, 24.4, 20.9. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₂₉F₃N₅: 528.2375; found: 528.2374.

TBI-709, 5-(4-Trifluoromethylphenyl)-3-(4-hydroxycyclohexyl)imino-2-(2-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.28 (d, J=3.6, 1H), 8.04 (d, J=8.4, 2H), 7.84 (d, J=7.2, 1H), 7.72˜7.69 (dd, J=8.1, J=1.5, 1H), 7.53 (d, J=8.1, 2H), 7,21˜7,12 (n), 3H), 6.60 (s, 1H), 6.44 (d, J=7.8, 1H), 5.17 (s, 1H), 3.74˜3.66 (m, 1H), 3.10˜3.04 (m, 1H), 2.53 (s, 3H), 2.05˜1.97 (m, 2H), 1.70˜1.67 (m, 2H), 1.50˜1.39 (m, 2H), 1.28˜1.17 (m, 2H). ¹³C NMR (100 MHz, CDCl₃) δ: 152.2, 151.0, 150.8, 144.3, 144.1, 140.8, 135.6, 134.7, 134.6, 131.0, 129.8, 129.2, 128.5, 128.4, 127.8, 123.2, 121.7, 113.7, 98.9, 89.1, 69.8, 56.8, 33.4, 31.1, 20.9. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₂₉F₃N₅O: 544.2324; found: 544.2324.

TBI-710, 5-(4-Trifluoromethylphenyl)-3-cyclohexylimino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.02 (d, J=8.1 Hz, 2H), 7.85˜7.80 (m, 2H), 7.72˜7.69 (dd, J=7.2, 1.2 Hz, 1H), 7.52 (d, J=8.4 Hz, 2H), 7.21˜7.10 (m, 2H), 6.93=6.90 (m, 2H), 6.43˜6.41 (m, 1H), 5.16 (s, 1H), 4.03 (s, 3H), 3.10˜3.04 (m, 1H), 1.78=1.74 (m, 2H), 1.60˜1.56 (m, 3H), 1.46˜1.15 (m, 5H). ¹³C NMR (100 MHz, CDCl₃) δ: 155.4, 151.3, 150.5, 142.8, 140.9, 138.7, 135.6, 134.5, 131.2, 129.9, 128.5, 128.4, 128.3, 127.7, 124.9, 124.6, 123.0, 116.8, 113.6, 100.1, 89.6, 67.1, 57.5, 53.7, 33.5, 25.9, 24.2. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₂₉F₃N₅O: 544.2324; found: 544.2327.

TBI-711, 5-(4-Trifluoromethylphenyl)-3-(1-methylethyl)(6-acetamino-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, DMSO-d₆) δ: 8.37 (brs, 1H), 8.27 (d, J=1.8 Hz, 1H), 8.24 (s, 1H), 8.03 (d, J=8.4 Hz, 2H), 7.78˜7.74 (dd, J=8.7, 1.8 Hz, 1H), 7.71 (d, J=7.2 Hz, 1H), 7.52 (d, J=8.4 Hz, 2H), 7.24˜7.12 (m, 2H), 6.72 (s, 1H), 6.40 (d, J=8.1 Hz, 1H), 5.24 (s, 1H), 3.48˜3.39 (m, 1H), 2.23 (s, 3H), 1.10 (d, J=6.3 Hz, 6H). ¹³C NMR (100 MHz, CDCl₃) δ: 168.4, 150.7, 150.4, 147.4, 144.4, 141.2, 140.8, 135.7, 134.7, 133.0, 132.4, 131.0, 129.8, 128.6, 128.5, 128.4, 127.8, 123.4, 114.2, 113.8, 99.1, 89.1, 49.3, 24.6, 23.4. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₆F₃N₆O: 531.2120; found: 531.2122.

TBI-712, 5-(4-Trifluoromethylphenyl)-3-(4-tetrahydropyranyl)imino-2-(6-acetamino-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, DMSO-d₆) δ: 8.29 (d, J=2.7 Hz, 1H), 8.25 (d, J=9.3 Hz, 1H), 8.17 (brs, 1H), 8.03 (d, J=8.4 Hz, 2H), 7.77˜7.70 (m, 2H), 7.52 (d, J=8.4 Hz, 2H), 7.24˜7.13 (m, H), 6.72 (s, 1H), 6.45 (d, J=7.8 Hz, 1H), 5.15 (s, 1H), 3.98˜3.93 (m, 2H), 3.40˜3.27 (m, 3H), 2.23 (s, 3H), 1.71˜1.57 (m, 4H). ¹³C NMR (100 MHz, CDCl₃) δ: 168.3, 151.0, 150.6, 147.4, 144.4, 142.2, 140.8, 135.6, 134.8, 132.8, 132.2, 130.8, 129.8, 128.6, 128.5, 127.8, 123.3, 114.1, 113.7, 98.9, 89.0, 66.1, 54.6, 33.4, 24.6. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₂₈F₃N₆O₂: 573.2225; found: 573.2227.

TBI-713, 5-(4-Trifluoromethylphenyl)-3-cyclohexylimino-2-(6-acetamino-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, DMSO-d₆) δ: 8.28 (d, J=2.4 Hz, 1H), 8.23 (d, J=8.7 Hz, 1H), 8.02 (d, J=8.1 Hz, 3H), 7.76˜7.72 (dd, J=9.0, 2.4 Hz, 1H), 7.71˜7.68 (m, 1H), 7.52 (d, J=8.1 Hz, 2H), 7.21˜7.11 (m, 2H), 6.69 (s, 1H), 6.44 (d, J=7.8 Hz, 1H), 5.15 (s, 1H), 3.06˜2.99 (m, 1H), 2.23 (s, 3H), 1.75˜1.71 (m, 2H), 1.61˜1.57 (m, 3H), 1.42˜1.07 (m, 5H). ¹³C NMR (100 MHz, CDCl₃) δ: 168.2, 150.9, 150.4, 147.2, 144.5, 142.1, 140.9, 135.6, 134.6, 133.0, 132.1, 131.0, 129.9, 128.5, 128.4, 128.3, 127.6, 123.1, 114.1, 113.6, 98.8, 89.4, 58.1, 33.6, 25.8, 24.7, 24.6. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₂H₃₀F₃N₆O: 571.2433; found: 571.2437.

TBI-714, 5-(4-Trifluoromethylphenyl)-3-(4-hydroxycyclohexyl)imino-2-(6-acetamino-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, DMSO-d₆) δ: 8.27 (d, J=2.4 Hz, 1H), 8.23 (d, J=8.7 Hz, 1H), 8.13 (brs, 1H), 8.02 (d, J=8.4 Hz, 2H), 7.75 (d, J=2.4 Hz, 1H), 7.71˜7.68 (m, 1H), 7.52 (d, J=7.8 Hz, 2H), 7.22˜7.11 (m, 2H), 6.69 (s, 1H), 6.43 (d, J=7.2, 1H), 5.15 (s, 1H), 3.70˜3.63 (m, 1H), 3.06˜2.99 (m, 1H), 2.22 (s, 3H), 2.03˜1.95 (m, 2H), 1.67˜1.63 (m, 2H), 1.50˜1.39 (m, 2H), 1.25˜1.13 (m, 2H). ¹³C NMR (100 MHz, CDCl₃) δ: 168.2, 151.0, 150.8, 147.3, 144.3, 142.2, 140.9, 135.6, 134.7, 132.9, 132.1, 131.0, 129.9, 128.5, 127.8, 125.0, 123.3, 114.1, 113.7, 98.9, 89.1, 69.9, 57.1, 33.6, 32.2, 31.2, 26.4, 24.7. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₂H F₃N₆O₂: 587.2382; found: 587.2379.

TBI-715, 5-(4-Trifluoromethylphenyl)-3-(4-methoxycyclohexyl)imino-2-(6-acetamino-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, DMSO-d₆) δ: 8.57 (brs, 1H), 8.28˜8.26 (m, 2H), 8.03 (d, J=8.4, 2H), 7.78˜7.72 (m, 2H), 7.52 (d, J=8.4 Hz, 2H), 7.23˜7.14 (m, 2H), 6.73 (s, 1H), 6.45 (d, J=8.1 Hz, 1H), 5.20 (s, 1H), 3.35 (s, 3H), 3.21˜3.15 (m, 1H), 3.09˜3.02 (m, 1H), 2.23 (s, 3H), 2.10˜2.05 (m, 2H), 1.71˜1.1.67 (m, 2H), 1.49˜1.38 (m, 2H), 1.19˜1.08 (m, 2H). ¹³C NMR (100 MHz, CDCl₃) δ: 168.5, 151.1, 150.5, 147.5, 144.2, 141.7, 140.7, 135.8, 134.7, 132.9, 132.5, 130.8, 129.7, 128.5, 128.0, 123.5, 114.3, 113.9, 99.2, 89.1, 78.3, 57.1, 55.8, 30.9, 29.8, 24.6. HRMS (ESI-TOF⁺): [M+H]⁺ calcd for C₃₃H₃₂F₃N₆O₂: 601.2539; found: 601.2538.

TBI-716, 5-(4-Trifluoromethylphenyl)-3-cyclopropylimino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.41 (br, 1H), 8.02 (d, J=8.1 Hz, 2H), 7.67˜7.64 (m, 2H), 7.54 (d, J=8.1 Hz, 2H), 7.19˜7.09 (m, 3H), 6.66 (s, 1H), 6.35 (d, J=7.8 Hz, 1H), 5.49 (s, 1H), 2.71 (br, 1H), 2.56 (s, 3H), 0.90˜0.87 (m, 2H), 0.82 (br, 2H). ¹³C NMR (100 MHz, CDCl₃) δ: 153.6, 152.3, 151.1, 144.2, 143.9, 140.9, 135.7, 134.4, 133.8, 131.2, 129.9, 129.8, 128.6, 128.3, 127.6, 123.2, 113.7, 98.8, 89.5, 32.9, 23.8, 10.0. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₃F₃N₅: 486.1905; found: 486.1907.

TBI-717, 5-(4-Trifluoromethylphenyl)-3-cyclohexylimino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.45 (d, J=2.4 Hz, 1H), 8.02 (d, J=8.1 Hz, 2H), 7.70˜7.66 (m, 2H), 7.54 (d, J=8.4 Hz, 2H), 7.21˜7.11 (m, 3H), 6.71 (s, 1H), 6.45˜6.42 (dd, J=7.8, 1.2 Hz, 1H), 5.15 (s, 1H), 3.06˜2.99 (m, 1H), 2.56 (s, 3H), 1.75˜1.71 (m, 2H), 1.61˜1.57 (m, 3H), 1.43˜1.11 (m, 5H). ¹³C NMR (100 MHz, CDCl₃) δ: 153.4, 151.0, 150.5, 144.5, 143.8, 140.9, 135.6, 134.5, 134.0, 131.0, 129.9, 129.5, 128.5, 128.3, 127.6, 123.2, 123.1, 113.6, 98.8, 89.5, 58.1, 33.6, 25.8, 24.6, 23.8. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₂₉F₃N₅: 528.2375; found: 528.2378.

TBI-718, 5-(4-Trifluoromethylphenyl)-3-cyclopropylimino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃)₆: 8.58 (brs, 1H), 8.02 (d, J=8.1 Hz, 2H), 7.84˜7.82 (m, 2H), 7.70˜7.67 (m, 1H), 7.54 (d, J=8.1 Hz, 2H), 7.20˜7.09 (m, 2H), 6.93˜6.89 (m, 2H), 6.35 (d, J=7.2 Hz, 1H), 5.49 (s, 1H), 4.01 (s, 3H), 2.71 (br, 1H), 0.91˜0.83 (m, 4H). ¹³C NMR (100 MHz, CDCl₃) δ: 155.5, 152.4, 151.4, 142.7, 140.9, 139.0, 135.7, 134.4, 131.4, 130.0, 128.6, 128.6, 128.2, 127.6, 125.1, 124.7, 123.0, 116.8, 113.6, 100.0, 89.7, 53.7, 32.9, 10.2. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₃F₃N₅O: 502.1854; found: 502.1854.

TBI-719, 5-(4-Trifluoromethylphenyl)-3-(4-hydroxycyclohexyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.03 (d, J=8.3 Hz, 2H), 7.86˜7.81 (m, 2H), 7.73˜7.70 (dd, J=7.2, J=1.5 Hz, 1H), 7.53 (d, J=8.4 Hz, 2H), 7.26 (s, 2H), 7.23˜7.12 (m, 2H), 6.94 (s, 1H), 6.92˜6.90 (m, 1H), 6.44˜6.41 (m, 1H), 5.16 (s, 1H), 4.03 (s, 3H), 3.76˜3.69 (m, 1H), 3.10˜3.03 (m, 1H), 2.05˜1.98 (m, 2H), 1.70˜1.66 (m, 2H), 1.53˜1.41 (m, 2H), 1.29˜1.16 (m, 1H). ¹³C NMR (100 MHz, CDCl₃) δ: 155.4, 151.2, 151.0, 142.8, 140.8, 138.9, 135.6, 134.6, 131.1, 129.9, 128.6, 128.5, 128.4, 127.8, 124.8, 123.2, 116.8, 113.7, 100.2, 89.3, 69.8, 56.8, 53.7, 33.2, 30.8. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₂₉F₃N₅O₂: 560.2273; found: 560.2271.

TBI-720, 5-(2-Trifluoromethylphenyl)-3-(1-methylethyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.59 (d, J=2.6, 1H), 8.33 (d, J=4.6, 1H), 8.05 (d, J=7.7 Hz, 1H), 7.94 (t, J=7.7 Hz, 1H), 7.81 (m, 2H), 7.70 (dd, J=7.7 Hz, 1.3, 1H), 7.41 (d, J=7.8 Hz, 1H), 7.35˜7.23 (m, 2H), 7.23˜7.02 (m, 2H), 6.83 (s, 1H), 6.28 (d, J=7.8 Hz, 1H), 5.07 (s, 1H), 3.39 (dt, J=12.6, 6.2 Hz, 1H), 1.20˜0.82 (m, 6H). ¹³C NMR (100 MHz, CDCl₃) δ: 150.9, 150.4, 144.3, 144.0, 143.5, 136.8, 135.5, 135.4, 135.2, 134.9, 131.8, 131.6, 130.5, 129.0, 128.9, 128.2, 128.0, 127.6, 123.6, 123.0, 114.2, 99.5, 90.1, 49.4, 23.6, 23.3. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₃F₃N₅: 474.1905; found: 474.1906.

TBI-721, 5-(4-Trifluoromethylphenyl)-3-(1-methylethyl)imino-2-(5-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.41 (d, J=2.1 Hz, 1H), 8.18 (s, 1H), 8.02 (d, J=8.3 Hz, 2H), 7.70 (dd, J=7.7, 1.3 Hz, 1H), 7.58 (s, 1H), 7.52 (d, J=8.2 Hz, 2H), 7.16 (dt, J=15.5, 6.7 Hz, 2H), 6.83 (s, 1H), 6.38 (d, J=8.7 Hz, 1H), 5.22 (s, 1H), 3.43 (dt, J=12.6, 6.2 Hz, 1H), 2.38 (s, 3H), 1.08 (d, J=6.2 Hz, 6H). ¹³C NMR (100 MHz, CDCl₃) δ: 151.0, 150.2, 145.0, 143.8, 141.2, 140.9, 136.3, 135.5, 134.6, 133.5, 131.2, 129.8, 128.5, 128.3, 127.7, 123.1, 113.7, 99.3, 89.1, 49.4, 23.5, 18.5. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₅F₃N₅: 488.2062; found: 488.2060.

TBI-722, 5-(4-Trifluoromethylphenyl)-3-cyclohexylimino-2-(5-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.40 (d, J=2.0 Hz, 1H), 8.18 (s, 1H), 8.03 (d, J=8.2 Hz, 2H), 7.71 (dd, J=7.6, 1.4 Hz, 1H), 7.57 (s, 1H), 7.52 (d, J=8.1 Hz, 2H), 7.24˜7.02 (m, 2H), 6.82 (s, 1H), 6.44 (d, J=7.2 Hz, 1H), 5.16 (s, 1H), 3.15˜2.86 (m, 1H), 2.38 (s, 3H), 1.75˜1.71 (m, 2H), 1.58 (br, 3H), 1.25 (ddt, J=43.9, 22.5, 11.3 Hz, 5H). ¹³C NMR (100 MHz, CDCl₃) δ: 151.1, 150.4, 145.0, 143.8, 141.1, 140.9, 136.3, 135.6, 134.6, 133.5, 131.1, 129.9, 128.5, 128.4, 128.3, 127.7, 123.1, 113.6, 99.3, 89.5, 58.1, 33.6, 25.8, 24.6, 18.5. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₂₉F₃N₅: 528.2375: found: 528.2372.

TBI-723, 5-(4-Trifluoromethylphenyl)-3-(4-tetrahydropyranyl)imino-2-(5-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.42 s, 1H), 8.20 (s, 1H), 8.04 (d, J=7.9 Hz, 2H), 7.74 (d, J=7.5 Hz, 1H), 7.58 (s, 1H), 7.53 (d, 7.8 Hz, 2H), 7.25˜7.13 (m, 2H), 6.86 (s, 1H), 6.46 (d, J=7.9 Hz, 1H), 5.16 (s, 1H), 3.68˜3.94 (m, 2H), 3.40˜3.33 (m, 3H), 2.39 (s, 3H), 1.82˜1.31 (m, 4H). ¹³C NMR (100 MHz, CDCl₃) δ: 151.0, 150.7, 145.3, 143.7, 141.2, 140.8, 136.2, 135.6, 134.8, 133.6, 131.0, 129.8, 128.7, 128.6, 128.0, 123.4, 113.8, 99.5, 89.0, 66.1, 54.5, 33.4, 18.5. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₂₇F₃N₅O: 530.2167: found: 530.2166.

TBI-724, 5-(4-Trifluoromethylphenyl)-3-(4-methoxycyclohexyl)imino-2-(5-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.39 (s, 1H), 8.18 (s, 1H), 8.02 (d, J=8.2 Hz, 2H), 7.71 (d, J=7.5 Hz, 1H), 7.58 (s, 1H), 7.52 (d, J=8.1 Hz, 2H), 7.26 (s, 1H), 7.25˜7.02 (m, 2H), 6.83 (s, 1H), 6.43 (d, J=7.9 Hz, 1H), 5.18 (s, 1H), 3.35 (s, 3H), 3.28˜3.12 (m, 1H), 3.12˜2.90 (m, 1H), 2.38 (s, 3H), 2.22˜1.86 (m, 2H), 1.69˜1.65 (m, 2H), 1.47˜1.36 (m, 2H), 1.21˜1.09 (m, 2H). ¹³C NMR (100 MHz, CDCl₃) δ: 150.9, 145.1, 143.7, 141.2, 140.8, 136.3, 135.6, 134.6, 133.5, 131.1, 129.8, 128.5, 128.4, 127.9, 123.2, 113.7, 99.4, 89.2, 78.4, 57.2, 55.8, 31.1, 29.7, 18.5. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₂H₃₁F₃N₅O: 558.2480; found: 558.2480.

TBI-725, 5-(4-Trifluoromethylphenyl)-3-cyclopropylimino-2-(5-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.36 (s, 1H), 8.18 (s, 1H), 8.02 (d, J=8.1 Hz, 2H), 7.68 (d, J=Hz, 1H), 7.55˜7.53 (m, 3H), 7.23˜6.99 (m, 2H), 6.78 (s, 1H), 6.36 (d, J=7.8 Hz, 1H), 5.49 (s, 1H), 2.88˜2.52 (m, 1H), 2.37 (s, 3H), 1.03˜0.60 (m, 4H). ¹³C NMR (100 MHz, CDCl₃) δ: 152.1, 151.2, 145.2, 143.6, 141.2, 140.9, 136.2, 135.7, 134.4, 133.5, 131.3, 129.9, 128.6, 128.6, 128.3, 127.7, 123.1, 113.6, 99.3, 89.5, 32.9, 18.5, 10.1. HRMS (ESI-TOF⁺): [M+H]⁺ calcd for C₂₈H₂₃F₃N₅: 486.1905; found: 486.1907.

TBI-726, 5-(4-Trifluoromethylphenyl)-3-cyclobutylimino-2-(5-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.38 (s, 1H), 8.16 (s, 1H), 8.00 (d, J=7.7 Hz, 2H), 7.69 (d, J=7.5, 1H), 7.63˜7.35 (m, 3H), 7.22˜6.99 (m, 2H), 6.81 (s, 1H), 6.39 (d, J=7.9 Hz, 1H), 4.99 (s, 1H), 4.03˜3.59 (m, 1H), 2.36 (s, 3H), 2.23˜1.88 (m, 4H), 1.70 (dt, J=17.6, 7.7 Hz, 2H). ¹³C NMR (100 MHz, CDCl₃) δ: 151.0, 150.9, 145.1, 143.7, 141.2, 140.8, 136.2, 135.6, 134.2, 133.5, 131.0, 129.9, 128.5, 128.4, 127.8, 123.3, 113.7, 99.4, 90.6, 54.8, 31.9, 18.4, 16.0. HRMS (ESI-TOF⁺): calcd for C₂₉H₂₅F₃N₅: 500.2062; found: 500.2061.

TBI-727, 5-(4-Trifluoromethylphenyl)-3-(4-hydroxycyclohexyl)imino-2-(5-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.39 (d, J=Hz, 1H), 8.18 (s, 1H), 8.03 (d, 8.3 Hz, 2H), 7.72 (d, J=6.5 Hz, 1H), 7.64˜7.39 (m, 3H), 7.25˜7.00 (m, 2H), 6.83 (s, 1H), 6.44 (d, J=7.1 Hz, 1H), 5.16 (s, 1H), 3.87˜3.50 (m, 1H), 3.20˜2.80 (m, 1H), 2.38 (s, 3H), 1.99 (d, J=11.7 Hz, 2H), 1.66 (d, J=13.9 Hz, 2H), 1.57˜1.33 (m, 2H), 1.25˜1.14 (m, 2H). ¹³C NMR (100 MHz, CDCl₃) δ: 151.0, 150.9, 145.1, 143.7, 141.1, 140.8, 136.2, 135.6, 134.6, 133.6, 131.0, 129.8, 128.5, 128.4, 127.9, 123.2, 113.7, 99.4, 89.2, 69.9, 57.1, 33.6, 31.2, 18.5. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₂₉F₃N₅O: 544.23242; found: 544.2321.

TBI-728, 5-(4-Trifluoromethylphenyl)-3-cyclobutylimino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.79 (s, 1H), 8.02 (d, J=8.2 Hz, 2H), 7.85˜7.81 (m, 2H), 7.73˜7.70 (dd, J=7.8, 1.5 Hz, 1H), 7.52 (d, J=8.2 Hz, 2H), 7.24˜7.04 (m, 2H), 6.93˜6.89 (m, 2H), 6.41 (d, J=8.1 Hz, 1H), 5.01 (s, 1H), 4.05 (s, 3H), 3.98˜3.70 (m, 1H), 2.3˜1.91 (m, 4H), 1.91˜1.47 (m, 2H). ¹³C NMR (100 MHz, CDCl₃) δ: 155.4, 151.3, 151.1, 142.8, 140.9, 139.0, 135.6, 134.1, 131.1, 123.0, 128.5, 128.4, 127.8, 124.9, 124.7, 123.2, 116.8, 113.7, 100.3, 90.8, 54.9, 53.7, 32.0, 16.1. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₅F₃N₅O: 516.2013: found: 516.2011.

TBI-729, 5-(4-Trifluoromethylphenyl)-3-cyclopropylimino-2-(2-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.29 (d, J=4.7 Hz, 1H), 8.02 (d, J=8.3 Hz, 2H), 7.77 (d, J=8.0 Hz, 1H), 7.66 (d, J=8.5 Hz, 1H), 7.54 (d, J=8.1 Hz, 2H), 7.20˜7.11 (m, 3H), 6.49 (s, 1H), 6.35 (d, J=7.7 Hz, 1H), 5.50 (s, 1H), 2.76˜2.72 (m, 1H), 2.51 (s, 3H), 1.04˜0.85 (m, 2H), 0.85˜0.65 (m, 2H). ¹³C NMR (100 MHz, CDCl₃) δ: 152.6, 152.0, 151.2, 144.6, 144.1, 140.9, 135.6, 134.4, 131.3, 129.9, 129.8, 128.6, 128.2, 127.6, 123.1, 121.7, 113.6, 98.8, 89.4, 32.9, 20.9, 10.2. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₃F₃N₅: 486.1905; found: 486.1906.

TBI-730, 5-(3-Trifluoromethylphenyl-3-(1-methylethyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.59 (d, J=2.4 Hz, 1H), 8.34 (d, J=3.8 Hz, 1H), 8.04˜7.84 (m, 2H), 7.78 (d, J=8.2 Hz, 1H), 7.70 (m, 2H), 7.60 (d, J=7.3 Hz, 1H), 7.30 (dd, J=8.2, 4.7 Hz, 1H), 7.25˜7.06 (m, 2H), 6.84 (s, 1H), 6.42 (d, J=7.1 Hz, 1H), 5.20 (s, 1H), 3.40 (dt, J=12.3, 6.2 Hz, 1H), 1.08 (t, J=0.8 Hz, 6H). ¹³C NMR (100 MHz, CDCl₃) δ: 150.9, 150.3, 144.3, 144.0, 143.7, 138.3, 136.8, 135.6, 134.8, 132.8, 132.1, 131.2, 128.5, 128.0, 127.8, 126.6, 126.5, 123.6, 123.2, 113.6, 99.5, 89.5, 49.5, 23.6, 23.2. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₃F₃N₅: 474.1903: found: 474.1905.

TBI-731, 5-(4-Trifluoromethylphenyl)-3-(1-methylethyl)imino-2-(6-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.15 (d, J=2.6 Hz, 1H), 8.02 (d, J=8.3 Hz, 2H), 7.75˜7.57 (m, 2H), 7.51 (d, J=8.2 Hz, 2H), 7.14 (m, 2H), 6.79 (d, J=8.8 Hz, 1H), 6.49 (s, 1H), 6.37 (d, J=8.1 Hz, 1H), 5.21 (s, 1H), 3.96 (s 3H), 3.57˜3.30 (m, 1H), 1.09 (d J=6.2 Hz, 6H). ¹³C NMR (100 MHz, CDCl₃) δ: 161.3, 150.9, 150.3, 146.0, 142.5, 141.0, 135.6, 135.1, 134.5, 131.0, 130.1, 129.9, 128.5, 128.2, 127.3, 123.1, 113.6, 111.0, 98.1, 89.1, 53.6, 49.4, 23.5. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₅F₃N₅O: 504.1012; found: 504.2011.

TBI-732, 5-(4-Trifluoromethylphenyl)-3-cyclohexylimino-2-(6-ethoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.15 (s, 1H), 8.02 (d, J=8.0 Hz, 2H), 7.65 (m, 3H), 7.52 (d, J=8.0 Hz, 2H), 7.24˜6.99 (m, 2H), 6.78 (d, J=8.7 Hz, 1H), 6.49 (s, 1H), 6.43 (d, J=8.2 Hz, 1H), 5.15 (s, 1H), 3.95 (s, 3H), 3.03 (m, 1H), 1.73 (d, J=11.0 Hz, 2H), 1.59 (d, J=11.5 Hz, 3H), 1.47˜0.86 (m, 5H). ¹³C NMR (100 MHz, CDCl₃) δ: 161.2, 151.0, 150.5, 146.0, 142.5, 141.0, 135.6, 135.1, 134.5, 131.0, 130.1, 129.9, 128.5, 128.2, 127.3, 123.0, 113.6, 111.0, 98.0, 89.4, 58.1, 53.6, 33.6, 25.8, 24.6. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₂₉F₃N₅O: 544.2322; found: 544.2324.

TBI-733, 5-(4-Trifluoromethylphenyl)-3-(4-tetrahydropyranyl)imino-2-(6-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.16 (d, J=2.3 Hz, 1H), 8.03 (d, J=8.2 Hz, 2H), 7.69 (dd, J=7.8, 1.4 Hz, 1H), 7.63 (dd, J=8.8, 2.7 Hz, 1H), 7.52 (d, J=8.2 Hz, 2H), 7.24˜7.05 (m, 2H), 6.80 (d, J=8.8 Hz, 1H), 6.52 (s, 1H), 6.44 (dd, J=8.0, 1.1 Hz, 1H), 5.14 (s, 1H), 4.10˜3.80 (m, 5H), 3.51˜3.15 (m, 3H), 1.81˜1.43 (m, 4H). ¹³C NMR (100 MHz, CDCl₃) δ: 161.4, 151.1, 150.7, 145.9, 142.6, 140.9, 135.6, 135.2, 134.7, 130.7, 129.9, 129.8, 128.5, 128.4, 128.3, 127.6, 123.3, 113.7, 111.1, 98.2, 89.0, 66.1, 54.6, 53.6, 33.4. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₂₇F₃N₅O₂: 546.2114: found: 546.2117.

TBI-734, 5-(4-Trifluoromethylphenyl)-3-cyclobutylimino-2-(2-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.31 (d, J=4.5 Hz, 1H), 8.04 (d, J=8.0 Hz, 2H), 7.80 (d, J=8.0 Hz, 1H), 7.70 (d, J=7.7 Hz, 1H), 7.52 (d, J=7.9 Hz, 2H), 7.16 (m, 3H), 6.54 (s, 1H), 6.42 (d, J=7.9 Hz, 1H), 5.04 (s, 1H), 3.89 (p, J=7.8 Hz, 1H), 2.57 (s, 3H), 2.14 (m, 2H), 2.01 (m, 2H), 1.90˜1.56 (m, 2H). ¹³C NMR (100 MHz, CDCl₃) δ: 152.7, 151.0, 150.8, 144.6, 144.3, 140.9, 135.6, 134.5, 134.2, 130.9, 129.9, 129.8, 128.5, 128.4, 127.7, 123.3, 121.7, 113.7, 99.0, 90.6, 54.8, 32.0, 21.0, 16.0. HRMS (ESI-TOF⁺): [M+H]⁺ calcd for C₂₉H₂F₃N₅: 500.2063; found: 500.2062.

TBI-735, 5-(4-Trifluoromethylphenyl)-3-(4-methoxycyclohexyl)imino-2-(6-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.14 (d, J=2.3 Hz, 1H), 8.02 (d, J=8.3 Hz, 2H), 7.68 (dd, J=7.8, 1.4 Hz, 1H), 7.63 (dd, J=8.8, 2.8 Hz, 1H), 7.51 (d, J=8.1 Hz, 2H), 7.23˜7.04 (m, 2H), 6.79 (d, J=8.8 Hz, 1H), 6.50 (s, 1H), 6.41 (dd, J=8.0, 1.1 Hz, 1H), 5.17 (s, 1H), 3.96 (s, 3H), 3.35 (s, 3H), 3.27˜3.12 (m, 1H), 3.05 (dq, J=10.8, 5.9 Hz, 1H), 2.05 (m, 2H), 1.68 (m, 2H), 1.55˜1.31 (m, 2H), 1.14 (m, 2H). ¹³C NMR (100 MHz, CDCl₃) δ: 161.3, 151.1, 150.8, 145.9, 142.5, 140.9, 135.6, 135.1, 134.6, 130.9, 130.0, 129.8, 128.5, 128.3, 127.5, 123.1, 113.7, 111.1, 98.7, 89.1, 78.5, 57.3, 55.7, 53.6, 31.1, 29.8.

TBI-736, 5-(4-Trifluoromethylphenyl)-3-cyclopropylimino-2-(6-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.10 (brs, 1H), 8.01 (d, J=8.2 Hz, 2H), 7.62 (2H), 7.53 (d, J=8.1 Hz, 2H), 7.12 (m, 2H), 6.77 (d, J=8.7 Hz, 1H), 6.43 (s, 1H), 6.34 (d, J=8.1 Hz, 1H), 5.48 (s, 1H), 3.95 (s, 3H), 2.84˜2.57 (m, 1H), 0.88 (m, 2H), 0.80 (m, 2H). ¹³C NMR (100 MHz, CDCl₃) δ: 161.4, 152.4, 151.2, 145.8, 142.7, 141.0, 135.7, 135.4, 134.4, 131.1, 129.9, 128.6, 128.2, 127.4, 123.1, 113.6, 111.1, 98.1, 89.4, 53.6, 32.9, 9.9.

TBI-737, 5-(4-Trifluoromethylphenyl)-3-cyclobutylimino-2-(6-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.15 (d, J=2.5 Hz, 1H), 8.02 (d, J=8.3 Hz, 2H), 7.68 (d, J=7.7 Hz, 1H), 7.63 (dd, J=8.8, 2.7 Hz, 1H), 7.51 (d, J=8.1 Hz, 2H), 7.15 (m, 2H), 6.79 (d, J=8.7 Hz, 1H), 6.49 (s, 1H), 6.41 (d, J=8.1 Hz, 1H), 5.01 (s, 1H), 3.96 (s, 3H), 3.87 (p, J=7.6 Hz, 1H), 2.28˜1.90 (m, 4H), 1,90˜1.60 (m, 2H). ¹³C NMR (100 MHz, CDCl₃) δ: 161.4, 151.2, 150.9, 145.9, 142.6, 141.0, 135.7, 135.2, 134.1, 132.2, 131.8, 130.8, 129.9, 128.5, 128.3, 127.5, 123.2, 113.7, 111.1, 98.2, 90.6, 54.9, 53.6, 32.0, 16.0. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₅F₃N₅O: 516.2009; found: 516.2011.

TBI-738, 5-(4-Trifluoromethylphenyl)-3-cyclobutylimino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.46 (brs, 1H), 8.03 (d, J=7.8 Hz, 2H), 7.71˜7.66 (m, 2H), 7.51 (d, J=8.1 Hz, 2H), 7.22˜7.11 (m, 3H), 6.72 (s, 1H), 6.42 (d, J=8.1 Hz, 1H), 5.02 (s, 1H), 3.89˜3.84 (m, 1H), 2.56 (s, 3H), 2.15˜2.00 (m, 4H), 1.80˜1.68 (m, 2H). ¹³C NMR (100 MHz, CDCl₃) δ: 153.6, 151.1, 150.9, 144.3, 143.9, 140.8, 135.7, 134.2, 133.9, 132.2, 131.9, 130.9, 129.9, 129.6, 128.5, 127.8, 123.2, 113.7, 98.9, 90.6, 54.8, 31.9, 23.8, 16.0.

TBI-739, 5-(2-Trifluoromethylphenyl)-3-(4-methoxycyclohexyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.57 (d, Hz, 1H), 8.35˜8.33 (dd, J=4.8, 1.2 Hz, 1H), 8.04 (d, J=7.6 Hz, 1H), 7.94 (t, J=7.3 Hz, 1H), 7.84˜7.78 (m, 2H), 7.71 (dd, J=7.6, 1.6 Hz, 1H), 7.41 (d, J=7.7 Hz, 1H), 7.32˜7.28 (dd, J=8.4, 4.8 Hz, 2H), 7.24˜7.05 (m, 2H), 6.84 (s, 1H), 6.34 (d, J=8.7 Hz, 1H), 5.02 (s, 1H), 3.36 (s, 3H), 3.28˜3.08 (m, 1H), 3.08˜2.83 (m, 1H), 2.06 (d, J=10.2 Hz, 2H), 1.66 (brs, 2H), 1.55˜1.23 (m, 2H), 1.23˜0.94 (m, 2H). ¹³C NMR (100 MHz, CDCl₃) δ: 151.2, 150.8, 144.3, 144.0, 143.5, 136.7, 135.5, 135.3, 135.1, 134.9, 131.7, 131.5, 130.6, 129.8, 129.6, 128.9, 128.9, 128.3, 127.9, 127.8, 123.6, 123.1, 114.2, 99.6, 90.2, 78.5, 57.6, 55.9, 31.3, 30.9, 30.0. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₂₉F₃N₅O: 544.2320; found: 544.2324.

TBI-740, 5-(3-Trifluoromethylphenyl)-3-(4-methoxycyclohexyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.58 (s, 1H), 8.34 (d, J=4.5 Hz, 1H), 7.95˜7.87 (q, J=8.3 Hz, 2H), 7.79 (d, J=8.3 Hz, 1H), 7.72 (d, J=7.4 Hz, 1H), 7.67 (s, 1H), 7.60 (d, J=7.2 Hz, 1H), 7.41˜7.28 (m, 2H), 7.25˜7.08 (m, 2H), 6.84 (s, 1H), 6.48 (d, J=7.7 Hz, 1H), 5.14 (s, 1H), 3.35 (s, 3H), 3.28˜3.09 (m, 1H), 3.09˜2.86 (m, 1H), 2.07 (d, J=12.3 Hz, 2H), 1.72˜1.61 (m, 2H), 1.57˜1.25 (m, 2H), 1.25˜0.94 (m, 2H). ¹³C NMR (125 MHz, CDCl₃) δ: 151.1. 150.9, 144.4, 144.0, 143.6, 138.2, 136.7, 135.6, 134.8, 134.3, 134.0, 132.7, 132.1, 131.1, 128.5, 128.0, 126.6, 126.3, 123.6, 123.3, 113.7, 99.6, 89.3, 78.5, 57.6, 55.8, 31.5, 30.9, 30.1, 29.8. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₂₉F₃N₅O: 544.2325; found: 544.2324.

TBI-741, 5-(4-Chlorophenyl)-3-(1-methylethyl)imino-2-(2-methoxy-3-pyridyl)amino-7-fluoro-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.89 (brs, 1H), 7.84˜7.81 on, 2H), 7.72 (d, J=8.4 Hz, 2H), 7.66˜7.61 (dd, J=8.7, 6.0 Hz, 1H), 7.29 (d, J=8.4 Hz, 2H), 6.93˜6.84 (m, 3H), 6.14˜6.10 (dd, J=10.8, 2.7 Hz, 1H), 5.30 (s, 1H), 4.04 (s, 3H), 3.51˜3.42 (m, 1H), 1.11 (d, J=6.3 Hz, 6H). HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₄ClFN₅O: 488.1654; found: 488.1653.

TBI-744, 5-(4-Trifluoromethylphenyl)-3-(2,3-dimethoxy-1-propyl)imino-2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.91 (s, 1H), 8.01 (d, J=8.1, 2H), 7.87˜7.82 (m, 2H), 7.74 (d, J=7.5, 1H), 7.51 (d, J=8.1, 2H), 7.26˜7.15 (m, 2H), 6.99 (s, 1H), 6.99˜6.91 (dd, J=7.2, J=4.5, 1H), 6.38 (d, J=7.8, 1H), 5.23 (s, 1H), 4.03 (s, 3H), 3.68˜3.64 (m, 2H), 3.58˜3.55 (m, 1H), 3.46 (s, 3H), 3.38 (s, 3H), 3.28˜3.24 (m, 2H). ¹³C NMR (125 MHz, CDCl₃) δ 155.3, 153.2, 150.9, 142.5, 140.7, 138.8, 135.6, 134.6, 131.1, 129.7, 128.8, 128.4, 128.0, 124.8, 124.5, 123.4, 116.9, 113.9, 100.1, 89.3, 81.0, 73.2, 59.3, 57.9, 53.7, 50.5.

TBI-422, 5-(4-Chlorophenyl)-3-cyclohexylimino-2-(3-pyridyl)amino-3,5-dihydrophenazine

mp: 194-196° C. ¹H NMR (300 MHz, CDCl₃) δ: 8.58 (d, J=2.7 Hz, 1H), 8.33 (d, J=4.5 Hz, 1H), 7.80-7.76 (m, 1H), 7.73-7.67 (m, 3H), 7.32-7.26 (m, 3H), 7.19-7.13 (m, 2H), 6.83 (d, J=1.2 Hz, 1H), 6.49-6.46 (m, 1H), 5.26 (s, 1H), 3.10 (m, I H), 1.76-1.73 (m, 2H), 1.64-1.59 (m, 3H), 1.40-1.37 (m, 2H), 1.26-1.22 (m, 3H). ¹³C NMR (100 MHz, CDCl₃) δ: 151.0, 150.4, 144.2, 143.9, 143.7, 136.8, 136.0, 135.7, 135.6, 134.8, 131.6, 131.5, 130.4, 128.3, 127.8, 127.7, 123.6, 123.0, 113.8, 99.4, 89.3, 57.8, 33.6, 25.8, 24.6, HRMS ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₇ClN₅: 480.1955: found: 480.1953.

TBI-427, 5-(4-Chlorophenyl)-3-(N-methyl-4-piperidyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

mp: 198-200° C. ¹H NMR (300 MHz, CDCl₃) δ: 8.60 (d, J=2.4 Hz, 1H), 8.35 (d, J=5.1 Hz, 1H), 7.80-7.77 (m, 1H), 7.74-7.70 (m, 3H), 7.33-7.29 (m, 3H), 7.22-7.13 (m, 2H), 6.85 (s, 1H), 6.49 (d, J=7.5 Hz, 1H), 5.25 (s, 1H), 3.15-3.13 (m, 1H), 2.81-2.77 (m, 2H), 2.30 (s, 3H), 2.04 (m, 2H), 1.68 (m, 4H). ¹³C NMR (100 MHz, CDCl₃) δ: 151.0, 144.4, 144.0, 143.6, 136.7, 136.0, 135.8, 134.9, 131.7, 130.3, 128.4, 127.9, 123.7, 123.2, 114.0, 99.5, 89.1, 53.9, 46.4, 32.7. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₈ClN₆: 495.2058: found: 495.2057.

TBI-428, 5-(4-Chlorophenyl)-3-(N-methyl-4-piperidylmethyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

mp: 188-190° C., ¹H NMR (300 MHz, CDCl₃) δ: 8.58 (d, J=2.4 Hz, 1H), 8.35 (dd, J=4.5 Hz, 1.2 Hz, 1H), 7.79-7.76 (m, 1H), 7.73-7.70 (m, 3H), 7.33-7.28 (m, 3H), 7.22-7.12 (m, 2H), 6.83 (s, 1H), 6.46 (d, J=7.8 Hz, 1H), 5.27 (s, 1H), 3.05 (d, J=11.4 Hz, 2H), 2.87 (d, J=11.4 Hz, 2H), 2.28 (s, 3H), 1.98-1.90 (m, 2H), 1.76-1.63 (m, 3H), 1.43-1.34 (m, 2H). ¹³C NMR (100 MHz, CDCl₃) δ: 152.2, 150.9, 144.4, 144.1, 143.6, 136.7, 135.9, 135.8, 135.6, 134.8, 131.8, 131.5, 130.2, 128.4, 128.2, 127.9, 125.0, 123.7, 123.1, 114.0, 99.3, 89.0, 55.9, 50.7, 46.5, 37.1, 30.8. HRMS ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₃₀ClN₆: 509.2215; found: 509.2219.

TBI-433, 5-(4-Chlorophenyl)-3-(2-morpholinoethyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

mp: 116-118° C. ¹H NMR (300 MHz, CDCl₃) δ: 8.60 (s, 1H), 8.35 (d, J=3.6 Hz, 1H), 7.80-7.77 (m, 1H), 7.74-7.71 (m, 3H), 7.33-7.29 (m, 3H), 7.23-7.21 (m, 2H), 6.89 (s, 1H), 6.51 (m, 1H), 5.30 (s, 1H), 3.74-3.71 (m, 4H), 3.36 (t, J=7.2 Hz, 2H), 2.71 (t, J=7.2 Hz, 2H), 2.50-2.47 (m, 4H). ¹³C NMR (100 MHz, CDCl₃) δ: 152.8, 144.5, 144.0, 143.4, 136.6, 135.8, 135.0, 131.9, 131.2, 130.2, 128.5, 128.1, 123.7, 114.2, 99.6, 89.0, 66.9, 59.8, 54.1, 47.8. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₈ClN₆O: 511.2013; found: 511.2014.

TBI-434, 5-(4-Chlorophenyl)-3-(4-tetrahydropyranyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

mp: 15-217° C. ¹H NMR (300 MHz, CDCl₃) δ: 8.61 (d, J=1.8 Hz, 1H), 8.36 (d, J=3.9 Hz, H), 7.80-7.77 (m, 1H), 7.74-7.72 (m, 3H), 7.34-7.29 (m, 3H), 7.24-7.14 (m, 2H), 6.87 (s, 1H), 6.50 (d, J=7.1 Hz, 1H), 5.26 (s, 1H), 4.01-3.97 (m, 2H), 3.49-3.37 (m, 3H), 1.73-1.65 (m, 4H). ¹³C NMR (100 MHz, CDCl₃) δ: 151.1, 150.7, 144.5, 144.0, 143.6, 136.6, 135.9, 135.8, 135.7, 135.0, 131.7, 131.3, 130.3, 128.5, 128.1, 128.0, 123.7, 123.2, 114.0, 99.6, 88.9, 66.1, 54.3, 33.4, HRMS (ESI-TOF⁺): m/z. [M+H]⁺ calcd for C₂₈H₂₅ClN₅O: 482.1742; found: 482.1741.

TBI-435, 5-(4-Chlorophenyl)-3-(N-isobutyl-4-piperidyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

mp: 209-210° C. ¹H NMR (300 MHz, CDCl₃) δ: 8.59 (m, 1H), 8.34 (d, J=4.8 Hz, 1H), 7.80-7.76 (m, 1H), 7.73-7.71 (m, 3H), 7.32-7.29 (m, 3H), 7.19-7.12 (m, 2H), 6.85 (s, 1H), 6.48 (d, J=7.8 Hz, 1H), 5.26 (s, 1H), 3.14 (m, 1H), 2.80-2.77 (m, 2H), 2.09-2.05 (m, 2H), 1.96-1.93 (m, 2H), 1.82-1.63 (m, 5H), 0.90 (d, J=6.6 Hz, 6H). ¹³C NMR (100 MHz, CDCl₃) δ: 150.8, 144.3, 143.9, 143.6, 136.8, 136.0, 135.6, 134.9, 131.6, 130.4, 128.4, 127.8, 123.6, 123.1, 113.9, 99.5, 89.2, 67.1, 55.9, 52.4, 32.9, 25.7, 21.0. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₂H₃₄ClN₆: 537.2533; found: 537.2546.

TBI-436, 5-(4-Chlorophenyl)-3-(4-methoxycyclohexyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

mp: 228-230° C. ¹H NMR (300 MHz, CDCl₃) δ: 8.58 (d, J=2.4 Hz, 1H), 8.34 (d, J=3.6 Hz, 1H), 7.80-7.77 (m, 1H), 7.72-7.69 (m, 3H), 7.32-7.28 (m, 3H), 7.22-7.13 (m, 2H), 6.84 (s, 1H), 6.50-6.47 (m, 1H), 5.27 (s, 1H), 3.37 (s, 3H), 3.24-3.08 (m, 2H), 2.10-2.06 (m, 2H), 1.72-1.69 (m, 2H), 1.48-1.38 (m, 2H), 1.26-1.15 (m, 2H). ¹³C NMR (100 MHz, CDCl₃) δ: 151.1, 144.4, 144.0, 143.6, 136.7, 135.9, 135.6, 134.9, 131.6, 130.3, 128.4, 127.9, 123.6, 123.1, 113.9, 99.5, 89.1, 78.5, 57.3, 55.8, 31.1, 29.9, HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₂₉ClN₅O: 510.2060; found: 510.2069.

TBI-437, 5-(4-Chlorophenyl)-3-(N-cyclopentyl-4-piperidyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

mp: 170-172° C. ¹H NMR (300 MHz, CDCl₃) δ: 8.58 (d, J=2.4 Hz, 1H), 8.35 (d, J=4.2 Hz, 1H), 7.79-7.76 (m, 1H), 7.74-7.71 (m, 3H), 7.33-7.29 (m, 3H), 7.23-7.14 (m, 2H), 6.86 (s, 1H), 6.50 (d, J=7.8 Hz, 1H), 5.26 (s, 1H), 3.20 (m, 1H), 2.97 (m, 2H), 2.52 (m, 1H), 2.05 (m, 2H), 1.90 (m, 2H), 1.71 (m, 4H), 1.55 (m, 6H). ¹³C NMR (100 MHz, CDCl₃) δ: 150.9, 144.4, 144.0, 143.6, 136.7, 136.0, 134.9, 131.7, 130.4, 128.4, 127.9, 123.7, 123.1, 113.9, 99.5, 89.1, 67.7, 55.4, 50.8, 32.8, 30.7, 24.2, HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₃H₃₄ClN₆: 549.2527; found: 549.2527.

TBI-438, 5-(4-Chlorophenyl)-3-(1-methylethyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.94 (brs, 1H), 7.86-7.81 (m, 2H), 7.72-7.67 (m, 3H), 7.30 (d, J=8.4 Hz, 2H), 7.19-7.09 (m, 2H), 6.93-6.89 (m, 2H), 6.44 (dd, J=7.5 Hz, 1.5 Hz, 1H), 5.28 (s, 1H), 4.04 (s, 3H), 3.51-3.42 (m, 1H), 1.11 (d, J=6.3 Hz, 6H). ¹³C NMR (125 MHz, CDCl₃) δ: 155.5, 151.3, 150.6, 143.0, 138.9, 136.1, 135.7, 134.8, 131.7, 130.5, 128.2, 127.6, 124, 122.9, 116.8, 113.8, 100.1, 89.3, 53.7, 49.4, 23.6,

TBI-439, 5-(4-Chlorophenyl)-3-(2-morpholinoethyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.83 (brs, 1H), 7.87-7.82 (m, 2H), 7.74-7.69 (m, 3H), 7.30 (d, J=8.4 Hz, 2H), 7.21-7.13 (m, 2H), 6.97 (s, 1H), 6.93 (dd, J=7.8 Hz, 4.5 Hz, 1H), 6.47 (dd, J=7.5 Hz, 1.5 Hz, 1H), 5.26 (s, 1H), 4.04 (s, 3H), 3.73 (t, J=4.5 Hz, 4H), 3.36 (t, J=6.9 Hz, 2H), 2.75 (t, J=7.2 Hz, 2H), 2.54 (t, J=4.5 Hz, 4H). ¹³C NMR (125 MHz, CDCl₃) δ: 155.3, 152.9, 151.0, 142.6, 138.9, 136.0, 135.8, 135.7, 134.9, 131.8, 131.5, 130.3, 128.4, 127.9, 124.8, 123.2, 116.8, 114.0, 100.2, 89.2, 67.0, 59.8, 54.3, 53.7, 48.5.

TBI-440, 5-(4-Chlorophenyl)-3-(N-methyl-4-piperidyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 9.13 (brs, 1H), 7.86-7.79 (m, 2H), 7.73-7.70 (m, 3H), 7.30 (d, J=8.4 Hz, 2H), 7.21-7.11 (m, 2H), 6.96 (s, 1H), 6.92 (dd, J=8.1 Hz, 5.4 Hz, 1H), 6.46 (dd, J=8.1 Hz, 1.5 Hz, 1H), 5.25 (s, 1H), 4.04 (s, 3H), 3.23 (m, 1H), 2.78-2.75 (m, 2H), 2.31 (s, 3H), 2.16 (m, 2H), 1.71-1.66 (m, 4H). ¹³C NMR (125 MHz, CDCl₃) δ: 155.3, 151.2, 150.9, 142.6, 138.6, 136.0, 135.7, 135.6, 134.9, 131.7, 131.5, 130.4, 128.3, 127.7, 125.0, 124.1, 123.0, 116.8, 113.9, 100.2, 89.1, 53.7, 53.4, 46.6, 32.7.

TBI-441, 5-(4-Chlorophenyl)-3-(1-methylethyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.45 (s, 1H), 7.71-7.66 (m, 3H), 7.29 (d, 0.4 Hz, 2H), 7.25 (m, 1H), 7.19-7.09 (m, 3H), 6.70 (s, 1H), 6.44 (d, J=7.5 Hz, 1H), 5.28 (s, 1H), 3.51-3.42 (m, 1H), 2.55 (s, 3H), 1.10 (d, J=6.3 Hz, 6H). ¹³C NMR (125 MHz, CDCl₃) δ: 153.4, 151.0, 150.4, 144.5, 143.9, 136.1, 135.7, 135.6, 134.8, 134.1, 131.7, 131.5, 130.4, 129.5, 128.3, 127.5, 123.2, 122.9, 113.8, 98.9, 89.1, 49.4, 23.8, 23.6.

TBI-442, 5-(4-Chlorophenyl)-3-(N-isobutyl-4-piperidyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 9.06 (brs, 1H), 7.86-7.79 (m, 2H), 7.73-7.69 (m, 3H), 7.30 (d, J=8.4 Hz, 2H), 7.20-7.11 (m, 2H), 6.95 (s, 1H), 6.91 (dd, J=7.8 Hz, 5.1 Hz, 1H), 6.46 (dd, J=7.8 Hz, 1.8 Hz, 1H), 5.25 (s, 1H), 4.04 (s, 3H), 3.21-3.17 (m, 1H), 2.79-2.75 (m, 2H), 2.11-2.05 (m, 4H), 1.84-1.64 (m, 5H), 0.91 (d, J=6.3 Hz, 6H). ¹³C NMR (125 MHz, CDCl₃) δ: 155.3, 151.2, 150.9, 142.7, 138.6, 136.1, 135.7, 134.9, 131.6, 131.5, 130.4, 128.3, 127.7, 125.0, 124.3, 123.0, 116.8, 113.8, 100.2, 89.2, 71.1, 67.4, 55.1, 53.7, 52.0, 32.8, 25.7, 21.1.

TBI-443, 5-(4-chlorophenyl)-3-(4-tetrahydropyranyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 9.09 (brs, 1H), 7.86-7.81 (m, 2H), 7.73-7.70 (m, 3H), 7.30 (d, J=8.4 Hz, 2H), 7.22-7.12 (m, 2H), 6.97 (s, 1H), 6.92 (dd, J=7.8 Hz, 5.4 Hz, 1H), 6.46 (dd, J=7.8 Hz, 1.2 Hz, 1H), 5.25 (s, 1H), 4.04 (s, 3H), 4.02-3.99 (m, 2H), 3.55-3.42 (m, 3H), 1.75-1.57 (m, 4H). ¹³C NMR (125 MHz, CDCl₃) δ: 155.3, 151.1, 151.0, 142.6, 138.7, 136.0, 135.8, 135.0, 131.7, 131.4, 130.4, 128.3, 127.8, 124.9, 124.3, 123.1, 116.8, 113.9, 100.3, 89.0, 65.5, 53.7, 53.3, 33.3.

TBI-444, 5-(4-Chlorophenyl)-3-(4-methoxycyclohexyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.97 (brs, 1H), 7.86-7.80 (m, 2H), 7.71-7.69 (m, 3H), 7.29 (d, J=8.4 Hz, 2H), 7.20-7.11 (m, 2H), 6.94 (s, 1H), 6.92 (dd, J=7.5 Hz, 4.8 Hz, 1H), 6.47 (d, J=7.5 Hz, 1H), 5.30 (s, 1H), 4.03 (s, 3H), 3.37 (s, 3H), 3.28-3.22 (m, 1H), 3.17-3.14 (m, 1H), 2.10-2.07 (m, 2H), 1.74-1.71 (m, 2H), 1.49-1.39 (m, 2H), 1.31-1.20 (m, 2H). ¹³C NMR (125 MHz, CDCl₃) δ: 151.2, 142.8, 138.8, 135.7, 131.6, 130.4, 128.3, 127.7, 124.9, 124.7, 123.0, 116.8, 113.9, 100.3, 89.3, 56.8, 55.8, 53.7, 30.7, 29.4.

TBI-445, 5-(4-Chlorophenyl)-3-(2-morpholinoethyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.45 (s, 1H), 7.73-7.66 (m, 3H), 7.30 (d, J=8.1 Hz, 2H), 7.25 (m, 1H), 7.19-7.16 (m, 3H), 6.74 (s, 1H), 6.47 (d, J=6.9 Hz, 1H), 5.28 (s, 1H), 3.72 (t, J=4.5 Hz, 4H), 3.36 (t, J=7.2 Hz, 2H), 2.71 (t, J=7.5 Hz, 2H), 2.57 (s, 3H), 2.48 (t, J=4.2 Hz, 4H). ¹³C NMR (125 MHz, CDCl₃) δ: 152.9, 150.7, 143.8, 136.0, 134.9, 133.9, 131.9, 130.3, 129.5, 128.4, 127.8, 123.2, 114.1, 99.0, 89.0, 67.0, 59.8, 54.1, 47.9, 23.9.

TBI-446, 5-(4-Chlorophenyl)-3-(N-methyl-4-piperidyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.45 (d, J=2.7 Hz, 1H), 7.73-7.66 (m, 3H), 7.30 (d, J=8.4 Hz, 2H), 7.25 (m, 1H), 7.21-7.12 (m, 3H), 6.73 (s, 1H), 6.48 (d, 7.8 Hz, 1H), 5.24 (s, 1H), 3.14-3.13 (m, 1H), 2.81-2.77 (m, 2H), 2.56 (s, 3H), 2.30 (s, 3H), 2.05 (m, 2H), 1.68 (m, 4H). ¹³C NMR (125 MHz, CDCl₃) δ: 153.5, 151.1, 144.4, 143.8, 136.0, 135.8, 134.9, 134.0, 131.6, 131.3, 130.4, 129.6, 128.4, 127.7, 123.2, 114.0, 99.0, 89.1, 53.9, 46.4, 32.7, 23.8.

TBI-447, 5-(4-Chlorophenyl)-3-(N-isobutyl-4-piperidyl)imino-2-(6-ethyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.45 (d, J=2.1 Hz, 1H), 7.73-7.66 (m, 3H), 7.30 (d, J=8.4 Hz, 2H), 7.25 (m, 1H), 7.20-7.11 (m, 3H), 6.72 (s, 1H), 6.47 (d, J=7.5 Hz, 1H), 5.25 (s, 1H), 3.14-3.11 (m, 1H), 2.80-2.77 (m, 2H), 2.56 (s, 3H), 2.08-2.05 (m, 2H), 1.98-1.92 (m, 2H), 1.81-1.62 (m, 5H), 0.90 (d, J=6.9 Hz, 6H). ¹³C NMR (125 MHz, CDCl₃) δ: 153.4, 151.0, 150.9, 144.4, 143.8, 136.1, 135.7, 134.8, 134.1, 131.6, 131.4, 130.4, 129.4, 128.3, 127.6, 123.2, 123.0, 113.9, 98.9, 89.2, 67.1, 56.0, 52.4, 32.9, 25.7, 23.8, 21.0.

TBI-448, 5-(4-Chlorophenyl)-3-(1-methylethyl)imino-2-(2-ethyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.28 (d, J=3.6 Hz, 1H), 7.81 (d, J=7.2 Hz, 1H), 7.73-7.66 (m, 3H), 7.31 (d, J=8.4 Hz, 2H), 7.20-7.10 (m, 3H), 6.58 (s, 1H), 6.45 (d, J=7.2 Hz, 1H), 5.29 (s, 1H), 3.53-3.45 (m, 1H), 2.55 (s, 3H), 1.11 (d, J=6.3 Hz, 6H). ¹³C NMR (100 MHz, CDCl₃) 152.3, 151.0, 150.3, 144.2, 136.1, 135.7, 135.6, 134.9, 134.7, 131.7, 131.4, 130.4, 129.2, 128.2, 127.6, 123.0, 121.6, 113.8, 98.8, 89.0, 67.1, 49.3, 23.6, 20.9,

TBI-449, 5-(4-Chlorophenyl)-3-(4-tetrahydropyranyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) 8.46 (d, J=2.4 Hz, 1H), 7.73-7.66 (m, 3H), 7.30 (d, J=8.4 Hz, 2H), 7.25 (m, 1H), 7.20-7.14 (m, 3H), 6.74 (s, 1H), 6.48 (dd, J=7.8 Hz, 1.5 Hz, 1H), 5.25 (s, 1H), 4.02-3.95 (m, 2H), 3.48-3.37 (m, 3H), 2.57 (s, 3H), 1.69-1.62 (m, 4H). ¹³C NMR (100 MHz, CDCl₃) δ: 153.6, 151.1, 150.7, 144.4, 143.8, 136.0, 135.8, 135.7, 135.0, 134.0, 131.6, 131.3, 130.3, 129.6, 128.4, 127.7, 123.2, 123.1, 113.9, 99.0, 89.0, 66.1, 54.3, 33.4, 23.8.

TBI-450, 5-(4-Chlorophenyl)-3-(4-methoxycyclohexyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.44 (d, J=2.4 Hz, 1H), 7.72-7.67 (m, 3H), 7.29 (d, J=8.7 Hz, 2H), 7.25 (m, 1H), 7.20-7.11 (m, 3H), 6.72 (s, 1H), 6.48 (d, J=7.5 Hz, 1H), 5.26 (s, 1H), 3.71 (s, 3H), 3.37-3.15 (m, 1H), 3.14-3.07 (m, 1H), 2.56 (s, 3H), 2.10-2.06 (m, 2H), 1.72-1.69 (m, 2H), 1.49-1.38 (m, 2H), 1.25-1.14 (m, 2H). ¹³C NMR (100 MHz, CDCl₃) δ: 153.4, 151.1, 150.9, 144.3, 143.8, 135.9, 135.8, 135.6, 134.8, 134.0, 131.6, 131.4, 130.3, 129.4, 128.3, 127.7, 123.2, 123.0, 113.9, 98.9, 89.1, 78.5, 67.1, 57.3, 55.8, 31.2, 29.9, 23.8.

TBI-451, 5-(4-Chlorophenyl)-3-cyclohexylimino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 7.86-7.79 (m, 2H), 7.72-7.67 (m, 3H), 7.30 (d, J=8.4 Hz, 2H), 7.19-7.09 (m, 2H), 6.92-6.89 (m, 2H), 6.46 (dd, J=7.8 Hz, 1.8 Hz, 1H), 5.25 (s, 1H), 4.03 (s, 3H), 3.18-3.12 (m, 1H), 1.79-1.77 (m, 2H), 1.59 (m, 3H), 1.48-1.22 (m, 5H). ¹³C NMR (100 MHz, CDCl₃) δ: 155.4, 151.4, 150.6, 142.9, 138.6, 136.1, 135.6, 134.7, 131.6, 130.5, 128.2, 127.6, 125.0, 124.5, 122.8, 116.8, 113.8, 100.1, 89.5, 57.3, 53.7, 33.5, 26.0, 24.2.

TBI-452, 5-(4-Chlorophenyl)-3-(4-tetrahydropyranyl)imino-2-(2-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.30-8.28 (m, 1H), 7.83 (d, J=8.1 Hz, 1H), 7.74-7.69 (m, 3H), 7.30 (d, J=8.7 Hz, 2H), 7.22-7.12 (m, 3H), 6.64 (s, 1H), 6.49 (dd, J=7.8 Hz, 1.2 Hz, 1H), 5.27 (s, 1H), 4.02-3.95 (m, 2H), 3.53-3.40 (m, 3H), 2.56 (s, 3H), 1.73-1.60 (m, 4H). ¹³C NMR (100 MHz, CDCl₃) δ: 152.1, 151.0, 150.7, 144.3, 144.0, 136.0, 135.8, 135.6, 135.0, 134.6, 131.7, 131.3, 130.3, 129.0, 128.3, 127.8, 123.2, 121.7, 114.0, 99.0, 88.8, 65.8, 53.7, 33.4, 21.0.

TBI-453, 5-(4-Chlorophenyl)-3-(4-methoxycyclohexyl)imino-2-(2-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.28 (dd, J=5.1 Hz, 1.5 Hz, 1H), 7.82 (dd, J=8.4 Hz, 1.5 Hz, 1H), 7.72-7.67 (m, 3H), 7.29 (d, J=8.4 Hz, 2H), 7.21-7.11 (m, 3H), 6.60 (s, 1H), 6.48 (dd, J=7.8 Hz, 1.2 Hz, 1H), 5.28 (s, 1H), 3.36 (s, 3H), 3.26-3.11 (m, 2H), 2.54 (s, 3H), 2.10-2.04 (m, 2H), 1.74-1.71 (m, 2H), 1.48-1.36 (m, 2H), 1.30-1.19 (m, 2H).

TBI-454, 5-(3-Methylthiophenyl)-3-(1-methylethyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.59 (brs, 1H), 8.33 (d, J=4.8 Hz, 1H), 7.80-7.77 (m, 1H), 7.70-7.68 (m, 1H), 7.65-7.60 (m, 1H), 7.50-7.48 (m, 1H), 7.32-7.29 (m, 1H), 7.20-7.08 (m, 4H), 6.84 (s, 1H), 6.54-6.51 (m, 1H), 5.32 (s, 1H), 3.51-3.43 (m, 1H), 2.52 (s, 3H), 1.11-1.08 (m, 6H).

TBI-455, 5-(3-Methylsulfinylphenyl)-3-(1-methylethyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.60 (brs, 1H), 8.34 (d, J=4.8 Hz, 1H), 7.97-7.94 (m, 2H), 7.79 (d, J=8.7 Hz, 1H), 7.72-7.64 (m, 2H), 7.54-7.52 (m, 1H), 7.33-7.28 (m, 1H), 7.22-7.17 (m, 2H), 6.84 (s, 1H), 6.41 (t, J=7.2 Hz, 1H), 5.21-5.19 (m, 1H), 3.42-3.38 (m, 1H), 2.83 (s, 3H), 1.10-1.05 (m, 6H).

TBI-456, 5-(4-Methylthiophenyl)-3-(1-ethylethyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) d: 8.59 (d, J=2.4 Hz, 1H), 8.32 (dd, J=4.8 Hz, 1.5 Hz, 1H), 7.80-7.76 (m, 1H), 7.68 (dd, J=8.1 Hz, 2.1 Hz, 1H), 7.54 (d, J=8.4 Hz, 1H), 7.31-7.23 (m, 4H), 7.19-7.09 (m, 2H), 6.84 (s, 1H), 6.51 (dd, J=7.8 Hz, 1.2 Hz, I H), 5.36 (s, 1H), 3.50-3.44 (m, 1H), 2.62 (s, 3H), 1.10 (d, J=6.3 Hz, 6H).

TBI-457, 5-(4-Methylsulfinylphenyl)-3-(1-methylethyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.59 (s, 1H), δ 8.34 (d, J=4.8 Hz, 1H), 8.09-7.97 (m, 2H), 6.84 (s, 1H), 6.41 (d, J=7.8 Hz, 1H), 5.23 (s, 1H), 3.46-3.38 (m, 1H), 2.90 (s, 3H), 1.08 (d, J=6.0 Hz, 6H).

TBI-458, 5-(4-Chlorophenyl)-3-(4-tetrahydrothiopyranyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.60 (d, J=2.7 Hz, 1H), 8.35 (d, J=4.2 Hz, 1H), 7.79-7.71 (m, 3H), 7.34-7.29 (m, 2H), 7.23-7.14 (m, 2H), 6.86 (s, 1H), 6.50 (d, J=8.1 Hz, 1H), 5.20 (s, 1H), 3.21-3.16 (m, 1H), 2.82-2.78 (m, 2H), 2.59-2.50 (m, 2H), 1.94-1.74 (m, 4H). ¹³C NMR (100 MHz, CDCl₃) δ: 150.7, 150.6, 144.5, 144.0, 143.6, 136.6, 135.9, 135.6, 135.0, 131.7, 131.3, 130.3, 128.5, 128.1, 128.0, 123.7, 123.2, 114.0, 99.6, 88.8, 56.3, 34.3, 26.6.

TBI-914, 7-Fluoro-5-(4-chlorophenyl)-3-(1-methylethyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.45 (1H, d, J=2.1 Hz), 7.72 (2H, d, J=8.1 Hz), 7.67 (1H, d, J=8.7, 2.1 Hz), 7.62 (1H, m), 7.29 (2H, d, J=8.1 Hz), 7.16 (1H, d, J=8.7 Hz), 6.87 (1H, m), 6.67 (1H, s), 6.13 (1H, m), 5.30 (1H, s), 3.47 (1H, m), 2.56 (3H, s), 1.10 (6H, d, J=6.6 Hz), ¹³C NMR (100 MHz, CDCl₃) δ: 161.4 (d, J=246 Hz), 153.4, 150.3, 144.2, 143.8, 136.0, 135.7, 134.4, 134.0, 132.4, 132.3, 131.9, 130.2, 129.7, 129.6, 129.4, 123.2, 110.6 (d, J=23 Hz), 100.7 (d, J=28 Hz), 98.8, 89.7, 58.4, 23.8, 23.5. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₄ClFN₅: 472.1699; found: 472.1677.

TBI-918, 7-Fluoro-5-(4-chlorophenyl)-3-cyclohexylimino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.44 (1H, d, J=2.4 Hz), 7.72 (2H, d, J=8.4 Hz), 7.66 (1H, d, J=8.1, 2.4 Hz), 7.62 (1H, dd, J=8.7, 6.0 Hz), 7.29 (2H, d, J=8.4 Hz), 7.16 (1H, d, J=8.1 Hz), 6.87 (1H, ddd, J=11.1, 8.7, 2.7 Hz), 6.67 (1H, s), 6.15 (1H, dd, J=11.1, 2.7 Hz), 5.27 (1H, s), 3.09 (1H, m), 2.56 (3H, s), 1.74 (2H, m), 1.59 (3H, m), 1.39 (2H, m), 1.20 (3H, m). ¹³C NMR (100 MHz, CDCl₃, δ: 161.6 (d, J=246 Hz), 153.4, 150.4, 144.3, 143.8, 136.0, 135.7, 134.3, 134.0, 132.4, 132.3, 131.8, 130.2, 129.9, 129.8, 129.4, 123.2, 110.4 (d, J=23 Hz), 100.6 (d, J=29 Hz), 98.8, 90.0, 60.0, 33.7, 25.8, 24.6, 23.8. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₂₈ClFN₅: 512.2012; found: 512.2028.

TBI-919, 7-Fluoro-5-(4-chlorophenyl)-3-(4-tetrahydropyranyl)imino-2-(6-methyl-3-pyridyl)amino)-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃, δ: 8.53 (1H, d, J=2.7 Hz), 7.72 (2H, d, J=8.4 Hz), 7.66 (H, d, J=8.4, 2.7 Hz), 7.63 (1H, dd, J=9.0, 5.7 Hz), 7.30 (2H, d, J=8.4 Hz), 7.16 (1H, d, J=8.4 Hz), 6.87 (1H, ddd, J=11.2, 9.0, 2.4 Hz), 6.67 (1H, s), 6.16 (1H, dd, J=11.2, 2.4 Hz), 5.26 (1H, s), 3.95 (2 D, m), 3.36 (3H, m), 2.56 (3H, s), 1.63 (4H, m). ¹³C NMR (100 MHz, CDCl₃. δ: 162.3 (d, J=250 Hz), 153.3, 150.2, 144.1, 143.6, 136.2, 135.5, 134.1, 133.8, 132.3, 132.2, 131.6, 130.0, 129.8, 129.6, 129.3, 123.1, 110.3 (d, J=22 Hz), 100.4 (d, J=28 Hz), 98.7, 90.1, 66.2, 54.7, 33.4, 23.8. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₆ClFN₅O: 514.1804; found: 514.1798.

TBI-925, 7-Fluoro-5-(4-chlorophenyl)-3-(4-methoxycyclohexyl)imino-2-(6-methyl-3-pyridyl)amino)-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃. δ: 8.44 (1H, br. s), 7.72 (2H, d, J=8.7 Hz), 7.65 (2H, m), 7.28 (2H, d, J=8.4 Hz), 7.16 (1H, d, J=8.7 Hz), 6.88 (1H, m), 6.67 (1H, s), 6.16 (1H, m), 5.28 (1H, s), 3.37 (3H, s), 3.20 (1H, m), 3.10 (1H, m), 2.56 (3H, s), 2.07 (2H, m), 1.69 (2H, m), 1.43 (2H, m), 1.19 (2H, m). ¹³C NMR (100 MHz, CDCl₃. δ: 161.7 (d, J=247 Hz), 153.5, 151.0, 1502, 144.1, 143.8, 136.2, 135.6, 134.4, 133.9, 132.4, 132.3, 131.8, 130.1, 129.8, 129.4, 123.2, 110.6 (d, J=24 Hz), 100.7 (d, J=29 Hz), 98.9, 89.8, 78.4, 57.3, 55.8, 31.2, 29.9, 23.8. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₀ClFN₅O: 542.2117; found: 542.2097.

TBI-924 7-Fluoro-5-(4-chlorophenyl)-3-(4-methoxycyclohexyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃. δ: 8.91 (1H, br. s), 7.81 (2H, 7.71 (2H, d, J=7.8 Hz), 7.64 (1H, m), 7.28 (2H, d, J=7.8 Hz), 6.85 (3H, m), 6.16 (1H, m), 5.28 (1H, s), 4.03 (3H, s), 3.37 (3H, s), 3.25 (1H, m), 3.14 (1H, m), 2.07 (2H, m), 1.71 (2H, m), 1.44 (2H, m), 1.24 (2H, m). ¹³C NMR (100 MHz, CDCl₃. δ: 161.7 (d, J=246 Hz), 155.3, 151.1, 150.4, 142.5, 138.8, 136.1, 135.5, 134.3, 132.6, 132.5, 131.8, 130.1, 129.8, 124.8, 124.5, 116.8, 110.5 (d, J=23 Hz), 100.7 (d, J=28 Hz), 100.2, 89.9, 78.2, 56.8, 55.8, 53.7, 30.7, 29.3. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₀ClFN₅O₂: 558.2067; found: 558.2043.

TBI-926, 7-Fluoro-5-(4-chlorophenyl)-3-(1-methylethyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃. δ: 8.89 (1H, br. s), 7.81 (2H, m), 7.71 (2H, d, J=7.8 Hz), 7.63 (1H, m), 7.29 (2H, d, J=7.8 Hz), 6.89 (3H, m), 6.11 (1H, m), 5.30 (1H, s), 4.03 (3H, s), 3.46 (1H, m), 1.10 (6H, d, J=6.3 Hz). ¹³C NMR (100 MHz, CDCl₃. δ: 161.7 (d, J=246 Hz), 155.5, 150.5, 150.4, 142.7, 138.9, 136.0, 135.7, 134.3, 132.6, 132.3, 131.9, 130.2, 129.8, 124.9, 124.6, 116.8, 110.4 (d-=23 Hz), 100.6 (d, J=28 Hz), 99.8, 89.9, 53.7, 49.5, 23.6. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₄ClFN₅O: 488.1648: found: 488.1629.

TBI-927, 7-Fluoro-5-(4-chlorophen-3-cyclohexylimino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃, δ: 8.88 (1H, br, s), 7.81 (2H, m), 7.72 (2H, d, J=8.1 Hz), 7.63 (1H, dd, J=8.4, 6.3 Hz), 7.29 (2H, d, J=8.1 Hz), 6.87 (3H, m), 6.14 (1H, dd, J=10.2, 2.1 Hz), 5.27 (1H, s), 4.03 (3H, s), 3.15 (1H, m), 1.78 (2H, m), 1.58 (3H, m), 1.38 (2H, m), 1.28 (3H, m). ¹³C NMR (100 MHz, CDCl₃. δ: 161.7 (d, J=246 Hz), 155.3, 150.6, 150.4, 142.6, 138.6, 135.9, 135.7, 134.2, 132.6, 132.3, 131.8, 130.2, 129.6, 124.9, 124.3, 116.8, 110.3 (d, J=23 Hz), 100.6 (d, J=29 Hz), 100.1, 90.1, 57.3, 53.7, 33.5, 25.9, 24.1. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₂₈ClFN₅O: 528.1961; found: 528.1952.

TBI-928, 7-Fluoro-5-(4-chlorophenyl)-3-(4-tetrahydropyranyl)imino-2-(2-methoxy-3-pyridyl)amino)-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃. δ: 9.04 (1H, br. s), 7.83 (2H, m), 7.73 (2H, d, J=8.7 Hz), 7.66 (1H, dd, J=8.4, 6.0 Hz), 7.29 (2H, d, J=8.7 Hz), 6.88 (3H, m), 6.14 (1H, dd, J=9.9, 2.1 Hz), 5.27 (1H, s), 4.04 (3H, s), 4.01 (2H, m), 3.50 (3H, m), 1.64 (4H, m). ¹³C NMR (100 MHz, CDCl₃, 161.7 (d, J=246 Hz), 155.3, 151.0, 150.2, 142.4, 138.8, 136.2, 135.6, 134.5, 132.5, 132.3, 131.9, 130.1, 129.9, 124.8, 124.3, 116.8, 110.7 (d, J=23 Hz), 100.6 (d, J=28 Hz), 100.3, 89.6, 65.5, 53.8, 53.3, 33.3. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₆ClFN₅O₂: 530.1754; found: 530.1746.

TBI-938, 8-Fluoro-5-(4-chlorophenyl)-3-(4-methoxycyclohexyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃. δ: 8,44 (1H, br. s), 7.68 (3H, m), 7.35 (1H, br. d, J=8.1 Hz), 7.27 (2H, m), 7.16 (1H, d, J=8.1 Hz), 6.84 (1H, m), 6.67 (1H, s), 6.42 (1H, dd, J=9.0, 4.5 Hz), 5.23 (1H, s), 3.36 (3H, s), 3.20 (1H, m), 3.09 (1H, m), 2.56 (3H, s), 2.06 (2H, m), 1.69 (2H, m), 1.43 (2H, m), 1.23 (2H, m). ¹³C NMR (100 MHz, CDCl₃. δ: 158.5 (d, J=240 Hz), 153.7, 151.9, 151.0, 145.0, 143.9, 136.4 (d, J=14 Hz), 135.8 (d, J=16 Hz), 134.6, 133.8. 132.0, 131.7, 130.8, 130.2, 129.7, 128.0, 123.2, 115.9 (d, J=22 Hz), 113.4 (d, J=22 Hz), 98.5, 88.8, 78.4, 57.3, 55.8, 31.1, 29.9, 23.8. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₀ClFN₅O: 542.2117; found: 542.2079.

TBI-943, 8-Fluoro-5-(4-chlorophenyl)-3-(1-methylethyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃. δ: 8.46 (1H, br. s), 7.70 (3H, m), 7.33 (3H, m), 7.17 (1H, d, J=7.8 Hz), 6.84 (1H, m), 6.67 (1H, s), 6.39 (1H, m), 5.27 (1H, s), 3.48 (1H, m), 2.56 (3H, s), 1.10 (6H, d, J=6.0 Hz). ¹³C NMR (100 MHz, CDCl₃. δ: 158.5 (d, J=241 Hz), 153.6, 152.0, 150.2, 145.1, 143.9, 136.3 (d, J=12 Hz), 135.8 (d, J=14 Hz), 134.6, 133.9, 132.0, 131.8, 130.5, 130.3, 129.7, 128.0, 123.2, 114.7 (d, J=23 Hz), 113.3 (d, J=22 Hz), 98.4, 88.8, 49.4, 23.8, 23.5. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₄ClFN₅: 472.1699; found: 472.1680.

TBI-929, 8-Fluoro-5-(4-chlorophenyl)-3-(1-methylethyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃. δ: 8.99 (1H, br. s), 7.84 (2H, m), 7.72 (2H, d, J=7.8 Hz), 7.37 (1H, dd, J=9.3, 2.1 Hz), 7.30 (2H, d, J=7.8 Hz), 6.96 (1H, dd, J=8.4, 6.0 Hz), 6.88 (1H, s), 6.84 (1H, m), 6.38 (1H, dd, J=9.0, 4.5 Hz), 5.27 (1H, s), 4.05 (3 s), 3.47 (1H, m), 1.12 (6H, d, J=6.0 Hz). ¹³C NMR (100 MHz, CDCl₃. δ: 158.5 (d, J=240 Hz), 155.5, 152.3, 150.4, 143.5, 139.1, 136.2 (d, J=12 Hz), 135.817 Hz), 134.5, 131.8, 130.4, 128.2, 125.2, 124.6, 116.8, 114.7 (d, J=25 Hz), 114.6, 114.5, 113.3 (d, J=23 Hz), 99.6, 89.0, 53.7, 49.4, 23.5. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₄ClFN₅O: 488.1648; found: 488.1629.

TBI-936, 8-Fluoro-5-(4-chlorophenyl)-3-(4-methoxycyclohexyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃. δ: 8.98 (1H, br. s), 7.82 (2H, m), 7.69 (2H, d, J=7.8 Hz), 7.37 (1H, dd, J=9.0, 2.1 Hz), 7.27 (2H, d, J=7.8 Hz), 6.88 (3H, m), 6.39 (1H, dd, J=8.7, 5.1 Hz), 5.23 (1H, s), 4.05 (3H, s), 3.36 (3H, s), 3.24 (1H, m), 3.13 (1H, m), 2.07 (2H, m), 1.71 (2H, m), 1.43 (2H, m), 1.24 (2H, m). ¹³C NMR (100 MHz, CDCl₃. 0: 158.5 (d, J=240 Hz), 155.4, 152.2, 151.0, 143.3, 139.1, 136.4 (d, J=12 Hz), 135.8 (d, J=12 Hz), 134.6, 131.7, 130.3, 128.2, 124.9, 124.6, 116.8, 114.9 (d, J=24 Hz), 114.7, 114.6, 113.4 (d, J=23 Hz), 99.8, 89.0, 78.2, 56.8, 55.8, 53.8, 30.7, 29.4. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₀ClFN₅O₂: 558.2067; found: 558.2044.

TBI-937, 8-Fluoro-5-(4-chlorophenyl)-3-(4-tetrahydropyranyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃. δ: 9.13 (1H, br. s), 7.85 (2H, m), 7.72 (2H, d, 8.1 Hz), 7.39 (1H, dd, J=8.7, 2.1 Hz), 7.29 (2H, d, J=8.1 Hz), 6.89 (3H, m), 6.42 (1H, m), 5.24 (1H, s), 4.04 (3H, s), 3.97 (2H, m), 3.49 (3H, m), 1.69 (4H, m). ¹³C NMR (100 MHz, CDCl₃. δ: 158.5 (d, J=241 Hz), 155.4, 152.0, 150.9, 143.2, 139.1, 135.8 (d, J=11 Hz), 134.8 (d, J=12 Hz), 133.8, 131.8, 130.3, 128.0, 124.6, 124.4, 116.8, 115.2 (d, 23 Hz), 114.9, 114.7, 113.4 (d, J=22 Hz), 99.9, 88.7, 65.5, 53.8, 53.3, 33.2. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₆ClFN₅O₂: 530.1754; found: 530.1728.

TBI-939, 7-Methoxy-5-(4-chlorophenyl)-3-(1-methylethyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.86 (1H, br. s), 7.83 (1H, dd, J=7.8, 1.5 Hz), 7.79 (1H, dd, J=5.1, 1.5 Hz), 7.70 (2H, d, J=8.7 Hz), 7.62 (1H, d, J=8.7 Hz), 7.29 (2H, d, J=8.7 Hz), 6.90 (2 m), 6.77 (1H, dd, J=8.7, 2.4 Hz), 5.91 (1H, d, J=2.4 Hz), 5.26 (1H, s), 3.94 (3H, s), 3.70 (3H, s), 3.44 (1H, m), 1.10 (6H, d, J=6.3 Hz). ¹³C NMR (100 MHz, CDCl₃) δ: 159.4, 155.3, 150.6, 148.9, 141.9, 138.4, 136.0, 135.7, 134.6, 132.8, 131.7, 130.6, 130.4, 129.4, 125.1, 124.4, 116.8, 109.3, 100.4, 98.9, 89.6, 55.5, 53.7, 49.3, 23.6. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₇ClN₅O₂: 500.1848; found: 500.1832.

TBI-941, 7-Methoxy-5-(4-chlorophenyl)-3-(4-methoxycyclohexyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃. δ: 8.09 (1H, br. s), 7.82 (1H, dd, J=8.4, 1.8 Hz), 7.77 (1H, m), 7.68 (2H, d, J=8.7 Hz), 7.62 (1H, d, J=8.7 Hz), 7.28 (2H, d, J=8.7 Hz), 6.90 (2H, m), 6.78 (1H, dd, J=8.7, 2.1 Hz), 5.92 (1H, d, J=2.1 Hz), 5.23 (1H, s), 4.02 (3H, s), 3.69 (3H, s), 3.36 (3H, s), 3.24 (1H, m), 3.12 (1H, m), 2.04 (2H, m), 1.69 (2H, m), 1.42 (2H, m), 1.23 (2H, m). ¹³C NMR (100 MHz, CDCl₃. δ: 159.5, 155.2, 151.3, 148.7, 141.7, 138.3, 135.9, 135.8, 134.6, 132.7, 131.6, 130.6, 130.3, 129.5, 125.1, 124.1, 116.8, 109.5, 100.5, 98.8, 89.5, 78.3, 56.7, 55.8, 55.5, 53.7, 30.7, 29.4. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₂H₃₃ClN₅O₃: 570.2266; found: 570.2241.

TBI-942, 7-Methoxy-5-(4-chlorophenyl)-3-(4-tetrahydropyranyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 9.02 (1H, br. s), 7.82 (1H, dd, J=7.8, 1.8 Hz), 7.79 (1H, dd, J=4.8, 1.8 Hz), 7.70 (2H, d, J=8.4 Hz), 7.65 (1H, d, J=8.4 Hz), 7.29 (2H, J=8.4 Hz), 6.95 (1H, s), 6.90 (1H, dd, J=7.8, 4.8 Hz), 6.80 (1H, dd, J=8.4, 2.4 Hz), 5.93 (1H, d, J=2.4 Hz), 5.23 (1H, s), 4.04 (3H, s), 4.01 (2H, m), 3.71 (3H, s), 3.48 (3H, m), 1.63 (4H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 159.5, 155.1, 151.1, 148.6, 141.6, 138.3, 135.9, 135.8, 134.8, 132.6, 131.7, 130.7, 130.3, 129.6, 125.1, 123.8, 116.8, 109.7, 100.6, 98.9, 893, 65.6, 55.5, 53.7, 53.2, 33.3. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₂₉ClN₅O₃: 542.1953: found: 542.1934.

TBI-894, 7-Methoxy-5-(4-chlorophenyl)-3-cyclopropylimino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 9.00 (1H, br. s), 7.78 (2H, m), 7.68 (2H, d, J=8.1 Hz), 7.60 (1H, d, J=8.7 Hz), 7.30 (2H, d, J=8.1 Hz), 6.87 (1H, dd, J=7.8, 5.1 Hz), 6.84 (1H, s), 6.74 (1H, dd, J=8.7, 2.1 Hz), 5.88 (1H, d, J=2.1 Hz), 5.52 (1H, s), 3.99 (3H, s), 3.68 (3H, s), 2.71 (1H, m), 0.87 (2H, m), 0.80 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 159.5, 155.3, 152.7, 149.1, 141.6, 138.4, 136.0, 135.6, 134.4, 132.9, 131.8, 130.7, 130.5, 129.4, 125.0, 124.5, 116.8, 109.2, 100.4, 98.9, 90.0, 55.5, 53.7, 53.2, 32.8, 9.9. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₄ClN₅O₂: 498.1691; found: 498.1667.

TBI-895, 7-Methoxy-5-(4-chlorophenyl)-3-cyclobutylimino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.92 (1H, br. s), 7.82 (H, dd, J=7.2, 1.5 Hz), 7.79 (1H, dd, J=5.4, 1.5 Hz), 7.70 (2H, d, J=8.4 Hz), 7.63 (1H, d, J=8.7 Hz), 7.29 (2H, d, J=8.4 Hz), 6.90 (2H, m), 6.78 (1H, dd, J=8.7, 2.4 Hz), 5.92 (1H, d, J=2.4 Hz), 5.07 (1H, s), 4.04 (3H, s), 3.88 (1H, m), 3.70 (3H, s), 2.17 (2H, m), 2.06 (2H, m), 1.75 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 159.5, 155.2, 151.5, 148.7, 141.7, 138.4, 136.0, 135.7, 134.2, 132.6, 131.7, 130.7, 130.4, 129.5, 125.0, 124.2, 116.8, 109.6, 100.6, 98.8, 91.1, 55.5, 54.8, 53.7, 32.0, 16.0. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₆ClN₅O₂: 512.1848; found: 512.1816.

TBI-944, 5-(3,4-Dichlorophenyl)-3-cyclopropylimino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.41 (1H, br. s), 7.82 (1H, d, J=8.7 Hz), 7.65 (2H, m), 7.52 (1H, d, J=1.8 Hz), 7.27 (1H, m), 7.15 (3H, m), 6.64 (1H, s), 6.42 (1H, J=7.5 Hz), 5.55 (1H, s), 2.79 (1H, m), 2.56 (3H, s), 0.94 (2H, m), 0.86 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 153.6, 152.1, 151.2, 144.2, 143.9, 136.8, 135.6, 135.4, 134.3, 133.8, 133.2, 131.3, 131.2, 129.7, 128.7, 128.3, 127.6, 123.2, 123.1, 113.6, 98.8, 89.6, 33.1, 23.8, 10.2. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₂Cl₂N₅: 486.1247; found: 486.1228.

TBI-945, 5-(3,4-Dichlorophenyl)-3-(4-tetrahydropyranyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR 300 MHz, CDCl₃) δ: 8.53 (1H, d, J=2.1 Hz), 7.98 (1H, dd, J=7.8, 1.8 Hz), 7.83 (1H, d, J=8.1 Hz), 7.69 (1H, dd, J=8.4, 2.7 Hz), 7.50 (1H, d, J=2.7 Hz), 7.43 (2H, m), 7.21 (2H, m), 7.14 (1H, s), 6.82 (1H, dd, J=7.8, 1.8 Hz), 5.70 (1H, s), 3.99 (2H, m), 3.45 (3H, m), 2.57 (3H, s), 1.67 (4H, m). ¹³C NMR (100 MHz, CDCl₃) (5; 154.2, 153.7, 144.4, 143.9, 136.7, 135.5, 135.3, 134.6, 133.8, 133.2, 131.3, 131.2, 129.7, 128.7, 128.3, 127.6, 123.3, 123.2, 115.1, 99.0, 89.3, 66.1, 54.3, 33.4, 23.9. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₆Cl₂N₅O: 530.1509; found: 530.1511.

TBI-948, 5-(3,4-Dichlorophenyl)-3-cyclobutylimino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.47 (1H, br. s), 7.82 (1H, d, J=8.7 Hz), 7.67 (2H, m), 7.50 (1H, br. s), 7.24 (1H, m), 7.15 (3H, m), 6.70 (1H, s), 6.48 (1H, br. d, J=7.5 Hz), 5.11 (1H, s), 3.94 (1H, m), 2.56 (3H, s), 2.21 (2H, m), 2.05 (2H, m), 1.79 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 153.6, 151.0, 150.9, 144.4, 143.8, 136.8, 135.6, 135.3, 134.3, 134.1, 133.9, 133.0, 131.2, 130.9, 129.6, 128.6, 128.4, 127.4, 123.3, 123.2, 113.7, 98.9, 90.6, 54.8, 32.0, 23.8, 16.1. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₄Cl₂N₅: 500.1317; found: 500.1335.

TBI-946, 5-(3,4-Dichlorophenyl)-3-cyclobutylimino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.79 (1H, br. s), 7.84 (3H, m), 7.69 (1H, d, J=7.5 Hz), 7.50 (1H, d, J=2.1 Hz), 7.23 (1H, m), 7.17 (2H, m), 6.91 (2H, m), 6.47 (1H, d, J=7.5 Hz), 5.11 (1H, s), 4.05 (3H, s), 3.95 (1H, m), 2.22 (2H, m), 2.08 (2H, m), 1.81 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 155.4, 151.2, 151.1, 142.8, 139.0, 136.7, 135.6, 135.3, 134.3, 134.0, 133.0, 131.3, 131.1, 128.6, 128.4, 127.8, 124.9, 124.7, 123.2, 116.8, 113.7, 100.3, 90.8, 54.8, 53.7, 32.0, 16.1. HRMS (ESI-TOF⁺): m/z [M+H]⁺ for C₂₈H₂₄Cl₂N₅O: 516.1352; found: 516.1322.

TBI-947, 5-(2,4-Dichlorophenyl)-3-(4-tetrahydropyranyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.56 (1H, br. s), 7.81 (3H, m), 7.68 (1H, d, J=7.8 Hz), 7.50 (1H, m), 7.37 (1H, d, J=8.1 Hz), 7.18 (2H, m), 6.91 (2H, m), 6.32 (1H, d, J=7.8 Hz), 5.17 (1H, s), 4.01 (3H, s), 3.96 (2H, m), 3.49 (3H, m), 1.68 (4H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 155.3, 151.2, 151.1, 142.8, 139.1, 136.7, 135.6, 135.3, 134.2, 134.0, 133.0, 131.3, 131.0, 128.6, 128.4, 127.7, 124.9, 124.7, 123.2, 116.8, 113.7, 100.1, 89.3, 65.5, 53.6, 33.1. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₆Cl₂N₅O₂: 546.1358: found: 546.1374.

TBI-893, 5-(2,4-Dichlorophenyl)-3-cyclobutylimino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 7.86 (1H, m), 7.82 (3H, m), 7.72 (1H, d, J=7.8 Hz), 7.60 (1H, dd, J=8.4, 2.1 Hz), 7.34 (1H, d, J=8.4 Hz), 7.19 (2H, m), 6.91 (2H, m), 6.38 (1H, d. J=7.8 Hz), 5.01 (1H, s), 4.05 (3H, s), 3.95 (1H, m), 2.20 (2H, m), 2.13 (2H, m), 1.78 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 155.5, 151.5, 151.3, 142.8, 139.0, 136.7, 135.7, 134.8, 133.3, 132.9, 131.9, 131.8, 130.3, 129.9, 128.4, 127.9, 125.1, 124.7, 123.3, 116.8, 113.2, 100.3, 90.5, 54.9, 53.7, 32.0, 16.1. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₄Cl₂N₅O: 516.1352; found: 516.1328.

TBI-949, 7-Fluoro-5-(3,4-dichlorophenyl)-3-(4-tetrahydropyranyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) 8.46 (1H, d, J=2.1 Hz), 7.85 (1H, d, J=8.1 Hz), 7.65 (2H, m), 7.49 (1H, d, J=2.4 Hz), 7.24 (1H, dd, J=8.1, 2.4 Hz), 7.17 (1H, d 8.7 Hz), 6.9) (1H, m), 6.69 (1H, s), 6.18 (1H, dd, J=10.2, 3.0 Hz), 5.29 (1H, s), 3.99 (2H, m), 3.44 (3H, m), 2.57 (3H, s), 1.66 (4H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 163.0 (d, J=246 Hz), 153.8, 150.8, 150.0, 144.2, 143.9, 136.3, 135.6, 134.8, 134.2, 133.8, 133.2, 132.3, 131.8 (d, J=11 Hz), 131.0, 130.0 (d, J=12 Hz), 129.7, 128.2, 123.3, 111.0 (d, J=23 Hz), 100.6 (d, J=28 Hz), 99.0, 89.7, 66.5, 54.4, 33.4, 23.9. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₅Cl₂FN₅O: 548.1288; found: 548.1339.

TBI-896, 7-Fluoro-5-(3,4-dichlorophenyl)-3-(1-methylethyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 840 (1H, d, J=2.1 Hz), 7.84 (1H, d, J=8.7 Hz), 7.66 (2H, m), 7.49 (1H, d, J=2.4 Hz), 7.24 (1H, dd, J=8.7, 2.4 Hz), 7.16 (1H, d, J=8.1 Hz), 6.90 (1H, m), 6.66 (1H, s), 6.13 (1H, br. d, J=9.9 Hz), 5.32 (1H, s), 3.52 (1H, m), 2.56 (3H, s), 1.13 (6H, d, J=6.6 Hz). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, J=246 Hz), 153.5, 150.6, 150.1, 144.2, 143.8, 136.4, 135.6, 134.7, 134.1, 133.9, 133.3, 132.2, 131.9 (d, J=12 Hz), 131.0, 130.0 (d, J=12 Hz), 129.6, 128.3, 123.2, 110.7 (d, J=23 Hz), 100.6 (d, J=28 Hz), 98.8, 89.8, 49.6, 23.8, 23.6. HRMS (ESI-TOF⁺); m/z [M+H]⁺ calcd for C₂₇H₂₂Cl₂FN₅; 506.1309; found: 506.1276.

TBI-897, 7-Fluoro-5-(3,4-dichlorophenyl)-3-(4-methoxycyclohexyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.44 (1H, d, J=2.1 Hz), 7.84 (1H, d, J=7.8 Hz), 7.64 (2H, m), 7.48 (1H, d, J=2.4 Hz), 7.24 (1H, dd, J=7.8, 2.4 Hz), 7.16 (1H, d, J=7.5 Hz), 6.90 (1H, m), 6.66 (1H, s), 6.13 (1H, br. d, J=10.5 Hz), 5.30 (1H, s), 3.37 (3H, s), 3.18 (2H, 2.56 (3H, s), 2.09 (2H, m), 1.71 (2H, m), 1.45 (2H, m), 1.23 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, J=246 Hz), 153.6, 150.8, 150.1, 144.1, 143.8, 136.2, 135.6, 134.8, 134.0, 133.9, 133.2, 132.2, 132.0 (d, J=12 Hz), 131.0, 130.0 (d, J=12 Hz), 129.5, 128.2, 123.2, 110.8 (d, J=24 Hz), 100.6 (d, J=29 Hz), 98.9, 89.9, 78.4, 57.4, 55.8, 31.2, 29.8, 23.8. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₂₉Cl₂FN₅O: 576.1626; found: 576.1629.

TBI-899, 7-Fluoro-5-(3,4-dichlorophenyl)-3-(1-methylethyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.52 (1H, br. s), 7.81 (3H, m), 7.62 (1H, m), 7.49 (1H, br. s), 7.25 (1H, br. d, J=7.8 Hz), 6.91 (2H, m), 6.83 (1H, s), 6.10 (1H, br. d, J=10.5 Hz), 5.31 (1H, s), 4.03 (3H, s), 3.51 (1H, m), 1.13 (6H, d, J=6.3 Hz). ¹³C NMR (100 MHz, CDCl₃) δ: 161.7 (d, J=247 Hz), 155.5, 151.0, 150.3, 142.7, 139.0, 136.4, 135.6, 134.7, 134.0, 133.3, 132.2 (d, J=12 Hz), 131.0, 129.8 (d, J=11 Hz), 128.4, 125.0, 124.7, 116.8, 110.7 (d, J=24 Hz), 100.6 (d, J=29 Hz), 100.0, 90.0, 53.7, 49.5, 23.6. HRMS (ESI-TOF⁺): m/z [M+H]⁺ for C₂₇H₂₃Cl₂FN₅O: 522.1258; found: 522.1227.

TBI-884, 7-Fluoro-5-(3,4-dichlorophenyl)-3-(4-tetrahydropyranyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.60 (1H, br. s), 7.84 (3H, m), 7.67 (1H, m), 7.50 (1H, br. s), 7.24 (1H, br. d, J=7.8 Hz), 6.93 (2H, m), 6.92 (1H, s), 6.17 (1H, br. d, J=9.6 Hz), 5.30 (1H, s), 4.05 (3H, s), 4.02 (2H, m), 3.50 (3H, m), 1.76 (4H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 161.8 (d, J=247 Hz), 155.3, 150.8, 150.2, 142.4, 138.9, 136.3, 135.6, 134.8, 134.2, 133.3, 132.3, 132.2 (d, J=12 Hz), 131.0, 130.0 (d, J=10 Hz), 128.2, 124.7, 124.3, 116.8, 110.9 (d, J=23 Hz), 100.6 (d, J=28 Hz), 100.3, 89.7, 65.5, 53.8, 53.3, 33.3. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₅Cl₂FN₅O₂: 564.1364; found: 564.1376.

TBI-885, 7-Fluoro-5-(3,4-dichlorophenyl)-3-cyclopropylimino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.53 (1H, br. s), 7.81 (3H, m), 7.61 (1H, m), 7.51 (1H, br. s), 7.24 (1H, br. d, J=7.5 Hz), 6.90 (2H, m), 6.81 (1H, s), 6.10 (1H, br. d, J=10.2 Hz), 5.56 (1H, s), 4.01 (3H, s), 2.79 (1H, m), 0.96 (2H, m), 0.88 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 161.7 (d, J=248 Hz), 155.4, 152.0, 150.7, 142.5, 139.0, 136.4, 135.6, 134.7, 133.8, 133.4, 132.3 (d, J=12 Hz), 131.2, 129.7 (d, J=10 Hz), 128.5, 125.1, 124.6, 116.8, 110.5 (d, J=23 Hz), 100.5 (d, J=28 Hz), 100.0, 90.4, 53.7, 33.2, 10.4. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₁Cl₂FN₅O: 520.1102; found: 520.1078.

TBI-886, 7-Fluoro-5-(3,4-dichlorophenyl)-3-cyclobutylimino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H-NMR (300 MHz, CDCl₃) δ: 7.83 (3H, m), 7.65 (1H, m), 7.49 (1H, br. s), 7.23 (1H, br. d, J=7.5 Hz), 6.90 (2H, m), 6.87 (1H, s), 6.15 (1H, br. d, J=8.7 Hz), 5.13 (1H, s), 4.05 (3H, s), 3.95 (1H, m), 2.22 (2H, m), 2.11 (2H, m), 1.79 (2H, m), ¹³C NMR (100 MHz, CDCl₃) δ: 161.6 (d, J=2=18 Hz), 155.5, 151.1, 150.4, 142.6, 139.0, 136.3, 135.5, 134.7, 133.6, 133.2, 132.1 (d, J=12 Hz), 131.1, 130.0 (d, J=10 Hz), 128.4, 124.9, 124.6, 116.8, 110.8 (d, J=23 Hz), 100.6 (d, J=28 Hz), 100.2, 91.5, 54.9, 53.8, 32.0, 16.1. HRMS ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₃Cl₂FN₅O: 534.1258; found: 534.1225.

TBI-887, 8-Fluoro-5-(3,4-dichlorophenyl)-3-(1-methylethyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.46 (1H, br. s), 7.82 (1H, d, J=8.7 Hz), 7.66 (1H, dd, J=8.1, 2.1 Hz), 7.49 (1H, d, J=2.1 Hz), 7.35 (1H, dd, J=9.0, 2.1 Hz), 7.24 (1H, dd, J=8.7, 2.1 Hz), 7.18 (1H, d, J=8.1 Hz), 6.87 (1H, m), 6.65 (1H, s), 6.38 (1H, dd, J=9.0, 4.5 Hz), 5.28 (1H, s), 3.50 (1H, m), 2.57 (3H, s), 1.13 (6H, d, J=6.3 Hz). ¹³C NMR (100 MHz, CDCl₃) δ: 158.7 (d, J=241 Hz), 153.8, 152.0, 150.1, 145.1, 143.9, 136.7, 136.4 (d, J=12 Hz), 135.5. 134.4 (d, J=10 Hz), 134.1, 133.8, 133.2, 131.2, 129.8, 128.5, 127.7, 123.2, 114.8 (d, J=23 Hz), 114.5, 113.5 (d, J=22 Hz), 98.5, 88.9, 49.5, 23.8, 23.6. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₃Cl₂FN₅: 506.1309; found: 506.1276.

TBI-888 8-Fluoro-5-(3,4-dichlorophenyl)-3-cyclopropylimino-2-(6-methyl-3-pyridinyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.42 (1H, br. s), 7.82 (1H, d, J=8.7 Hz), 7.64 (1H, dd, J=8.1, 2.4 Hz), 7.50 (1H, d, J=1.8 Hz), 7.33 (1H, dd, J=9.0, 2.4 Hz), 7.25 (1H, dd, J=8.7, 1.8 Hz), 7.16 (1H, d, J=8.1 Hz), 6.85 (1H, m), 6.60 (1H, s), 6.35 (1H, dd, J=9.3, 5.1 Hz), 5.53 (1H, s), 2.80 (1H, m), 2.56 (3H, s), 0.96 (2H, m), 0.87 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 158.7 (d, J=240 Hz), 153.9, 152.2, 151.9, 144.9, 144.0, 136.8, 136.5 (d, J=12 Hz), 135.5, 134.5 (d, J=10 Hz), 134.1, 133.6, 133.3, 131.3, 129.9, 128.6, 127.8, 123.3, 114.6 (d, J=23 Hz), 114.5, 113.5 (d, J=22 Hz), 98.4, 89.3, 33.2, 23.8, 10.3. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₁Cl₂FN₅: 504.1153; found: 504.1122.

TBI-873, 8-Fluoro-5-(3,4-dichlorophenyl)-3-(4-tetrahydropyranyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.46 (1H, br. s), 7.83 (1H, d, 8.1 Hz), 7.66 (1H, dd, J=8.4, 2.4 Hz), 7.50 (1H, br. s), 7.37 (1H, d, 8.1 Hz), 7.24 (1H, m), 7.17 (1H, d, J=8.4 Hz), 6.89 (1H, m), 6.68 (1H, s), 6.43 (1), m), 5.25 (1H, s), 3.97 (2H, m), 3.44 (3H, m), 2.56 (3H, s), 1.67 (4H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 158.7 (d, J=240 Hz), 154.0, 151.7, 150.8, 144.9, 144.0, 136.7, 136.5 (d, J=12 Hz), 135.5, 134.5 (d, J=10 Hz), 134.3, 133.6, 133.2, 131.1, 129.9, 128.4, 127.4, 123.3, 114.8 (d, J=25 Hz), 114.6, 113.6 (d, J=22 Hz), 98.7, 88.8, 66.0, 54.3, 33.4, 23.9. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₅Cl₂FN₅O: 548.1288; found: 548.1312.

TBI-878, 8-Fluoro-5-(3,4-dichlorophenyl)-3-(4-methoxycyclohexyl)imino-2-(6-methyl-3-pyridinyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.45 (1H, br. s), 7.82 (1H, J=8.1 Hz), 7.65 (1H, dd, J=8.4, 2.4 Hz), 7.49 (1H, br. s), 7.36 (1H, d, J=8.1 Hz), 7.25 (1H, m), 7.18 (1H, d, J=8.4 Hz), 6.90 (1H, m), 6.69 (1H, s), 6.44 (1H, m), 5.49 (1H, s), 3.37 (3H, s), 3.25 (1H, m), 3.13 (1H, m), 2.57 (1H, s), 2.05 (2H, m), 1.68 (2H, m), 1.43 (2H, m), 1.23 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 158.7 (d, J=241 Hz), 154.0, 151.6, 150.7, 144.9, 144.0, 136.7, 136.4 (d, J=11 Hz), 135.5, 134.6 (d, J=11 Hz), 134.3, 133.6, 133.2, 131.1, 129.9, 128.4, 127.4, 123.3, 114.9 (d, J=25 Hz), 114.6, 113.7 (d, J=22 Hz), 98.9, 89.1, 78.4, 57.3, 55.8, 31.2, 29.7, 23.8. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₂₉Cl₂FN₅O: 576.1626; found: 576.1629.

TBI-859, 8-Fluoro-5-(4-chlorophenyl)-3-cyclopropylimino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.62 (1H, br. s), 7.81 (2H, m), 7.70 (2H, d, J=7.8 Hz), 7.35 (1H, dd, J=9.3, 2.1 Hz), 7.31 (2H, d 7.8 Hz), 6.91 (1H, dd, J=8.4, 6.0 Hz), 6.83 (1H, s), 6.82 (1H, m), 6.34 (1H, dd, J=9.0, 4.5 Hz), 5.52 (1H, s), 4.01 (3H, s), 2.75 (1H, m), 0.91 (2H, m), 0.85 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 158.6 (d, J=240 Hz), 155.5, 152.4, 152.3, 143.3, 139.3, 135.9 (d. J=12 Hz), 135.8 (d, J=17 Hz), 134.4, 131.8, 130.5, 128.4, 125.4, 124.5, 116.8, 114.8 (d, J=25 Hz), 114.6, 114.5, 113.3 (d, J=23 Hz), 99.6, 89.4, 53.7, 33.0, 10.2. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₂ClFN₅O: 486.1491; found: 486.1518.

TBI-874, 8-Fluoro-5-(3,4-dichlorophenyl)-3-(1-methylethyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.52 (1H, br. s), 7.81 (3H, m), 7.62 (1H, m), 7.49 (1H, br. s), 7.25 (1H, br. d, J=7.8 Hz), 6.91 (2H, m), 6.83 (1H, s), 6.10 (1H, br. d, J=10.5 Hz), 5.31 (1H, s), 4.03 (3H, s), 3.51 (1H, m), 1.13 (6H, d, J=6.3 Hz). ¹³C NMR (100 MHz, CDCl₃) δ: 158.8 (d 233 Hz), 155.7, 151.5, 150.3, 143.4, 139.5, 136.7, 136.5 (d, J=11 Hz), 135.5, 134.5, 134.3, 133.2, 131.1, 128.5, 127.8, 125.9, 124.1, 116.8, 114.9 (d, 24 Hz), 114.5 (d, J=10 Hz), 113.8 (d, J=22 Hz), 99.9, 89.1, 53.7, 49.5, 23.4. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₃Cl₂FN₅O: 522.1258; found: 522.1231.

TBI-875, 8-Fluoro-5-(3,4-dichlorophenyl)-3-cyclopropylimino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 7.83 (3H, m), 7.51 (1H, d, J=1.8 Hz), 7.36 (1H, dd, J=9.0, 2.1 Hz), 7.24 (1H, m), 6.88 (2H, m), 6.82 (1H, s), 6.37 (1H, dd, J=9.0, 4.5 Hz), 5.25 (1H, s), 4.02 (3H, s), 2.79 (1H, m), 0.96 (2H, m), 0.87 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 158.6 (d, J=240 Hz), 155.5, 152.5, 152.0, 143.4, 139.3, 136.8, 136.5 (d, 11 Hz), 135.5, 134.4, 134.1, 133.3, 131.3, 128.7, 128.0, 125.5, 124.4, 116.8, 114.7 (d, J=24 Hz), 114.4 (d, J=10 Hz), 113.5 (d, J=23 Hz), 99.4, 89.6, 53.7, 33.2, 10.5. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₁Cl₂FN₅O: 520.1102; found: 520.1071.

TBI-877, 8-Fluoro-5-(3,4-dichlorophenyl)-3-(4-tetrahydropyranyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 7.82 (3H, m), 7.49 (1H, br. s), 7.37 (1H, dd, J=8.7, 2.4 Hz), 7.23 (1H, m), 6.92 (2H, m), 6.91 (1H, s), 6.41 (1H, dd, J=8.4, 5.1 Hz), 5.26 (1H, s), 4.03 (3H, s), 4.01 (2H, m), 3.51 (3H, m), 1.71 (4H, ¹³C NMR (100 MHz, CDCl₃) δ: 158.8 (d, J=242 Hz), 155.5, 152.5, 143.2, 142.7, 139.3, 136.6, 136.3 (d, J=11 Hz), 135.5, 134.7, 134.4, 133.2, 131.3, 128.6, 128.2, 127.6, 124.5, 116.8, 115.1 (d, J==24 Hz), 114.5 (d, J=10 Hz), 113.6 (d, J=23 Hz), 100.1, 88.8, 65.5, 55.3, 53.8, 33.2. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₁₅Cl₂FN₅O₂: 564.1364; found: 564.1323.

TBI-879, 8-Fluoro-5-(3,4-dichlorophenyl)-3-(4-methoxycyclohexyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) (j: 7.83 (3H, m), 7.50 (1H, d, J=1.8 Hz), 7.39 (1H, dd, J=9.0, 14 Hz), 7.24 (1H, m), 6.93 (2H, m), 6.91 (1H, s), 6.44 (1H, dd, J=8.7, 4.5 Hz), 5.26 (1H, s), 4.04 (3H, s), 3.37 (3H, s), 3.27 (1H, m), 3.17 (1H, m), 2.08 (2H, m), 1.69 (2H, m), 1.44 (2H, m), 1.26 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 158.7 (d, J=240 Hz), 155.5, 152.2, 150.9, 143.3, 139.2, 136.6, 136.4 (d, J=12 Hz), 135.5, 134.6, 134.3, 133.2, 131.2, 128.4, 127.8, 125.0, 124.5, 116.8, 115.0 (d, J=24 Hz), 114.5 (d, J=10 Hz), 113.6 (d, J=22 Hz), 99.8, 89.1, 78.2, 56.9, 55.8, 53.8, 30.6, 29.3. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₂₉Cl₂F₅O₂: 592.1677; found: 592.1662.

TBI-889, 8-Fluoro-5-(4-trifluoromethoxyphenyl)-3-(1-methylethyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 7.83 (2H, m), 7.58 (2H, d, J=8.1 Hz), 7.39 (3H, m), 6.90 (2H, m), 6.88 (1H, s), 6.37 (1H, dd, J=015.1 Hz), 5.20 (1H, s), 4.04 (3H, s), 3.43 (1H, m), 1.11 (6H, d, J=6.3 Hz). ¹³C NMR (100 MHz, CDCl₃) δ: 158.6 (d, J=240 Hz), 155.6, 152.3, 150.4, 149.8, 143.9, 139.2, 136.3 (d, J=10 Hz), 135.8, 134.6, 130.8, 129.4, 128.2, 125.3, 124.6, 123.7, 116.8, 114.8 (d, J=24 Hz), 114.5 (d, J=9 Hz), 113.4 (d, J=22 Hz), 99.6, 89.1, 53.8, 49.5, 23.5. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₄F₄N₅O₂: 538.1861; found: 538.1880.

TBI-876, 8-Fluoro-5-(4-trifluoromethoxyphenyl)-3-cyclopropylimino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.62 (1H, br. s), 7.83 (2H, m), 7.58 (2H, d, J=8.1 Hz), 7.42 (2H, d, J=8.1 Hz), 7.35 (1H, dd, J=9.3, 2.1 Hz), 6.91 (2H, m), 6.84 (1H, s), 6.35 (1H, dd, J=8.1, 5.1 Hz), 5.48 (1H, s), 4.01 (3H, s), 2.71 (1H, m), 0.89 (2H, m), 0.83 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 158.6 (d, J=240 Hz), 155.5, 152.5, 152.4, 149.7, 143.3, 139.3, 136.5 (d, J=11 Hz), 135.8, 134.5, 130.9, 128.4, 125.4, 124.5, 123.7, 121.7, 116.8, 114.7 (d, J=24 Hz), 114.5 (d, J=9 Hz), 113.4 (d, J=22 Hz), 99.6, 89.4, 53.7, 33.0, 10.2. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₂F₄N₅O: 536.1704: found: 536.1735.

TBI-861, 8-Fluoro-5-(4-trifluoromethoxyphenyl)-3-(4-methoxycyclohexyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) 7.85 (2H, m), 7.59 (2 d, 7.8 Hz), 7.40 (2H, J=7.8 Hz), 7.35 (1H, dd, J=9.3, 2.1 Hz), 6.93 (2H, m), 6.88 (1H, s), 6.42 (1H, m), 5.17 (1H, s), 4.02 (1H, s), 3.35 (3H, s), 3.23 (1H, m), 3.10 (1H, m), 2.06 (2H, m), 1.68 (2H, m), 1.43 (2H, m), 1.23 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 158.6 (d, J=240 Hz), 155.5, 152.2, 151.1, 149.8, 143.3, 139.2, 136.4 (d, J=11 Hz), 135.8, 134.7, 130.7, 128.1, 125.0, 124.6, 123.8, 121.7, 116.9, 114.9 (d, J=26 Hz), 114.6 (d, J=9 Hz), 113.5 (d, J=22 Hz), 99.8, 89.0, 78.2, 57.0. 55.9, 53.7, 30.7, 29.4. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₂H₃₀F₄N₅O₃: 608,2207: found: 608.2181.

TBI-862, 8-Fluoro-5-(4-trifluoromethoxyphenyl)-3-cyclohexylimino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 7.83 (2H, m), 7.59 (2H, d, J=7.8 Hz), 7.40 (3H, m), 6.92 (2H, m), 6.87 (1H, s), 6.42 (1H, m), 5.17 (1H, s), 4.03 (3H, s), 3.08 (1H, m), 1.76 (2H, m), 1.58 (3H, m), 1.41 (2H, m), 1.25 (3H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 158.6 (d, J=240 Hz), 155.5, 152.4, 150.5, 149.7, 143.4, 139.1, 136.2 (d, J=11 Hz), 135.9, 134.6, 130.8, 128.1, 125.0, 124.7, 123.9, 121.7, 116.8, 114.9 (d, J=24 Hz), 114.5 (d, J=9 Hz), 113.5 (d, 22 Hz), 99.7, 89.3, 57.7, 53.7, 33.5, 25.9, 24.3. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₂₈F₄N₅O₂: 578.2174; found: 578.2114.

TBI-863, 8-Fluoro-5-(4-trifluoromethoxyphenyl)-3-(1-methylethyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) (15: 8.46 (1H, d, J=2.1 Hz), 7.67 (1H, dd, J=8.1, 2.4 Hz), 7.59 (2H, d, 8.1 Hz), 7.40 (2H, d, J=8.1 Hz), 7.37 (1H, m), 7.17 (1H, d, J=8.1 Hz), 6.85 (1H, m), 6.68 (1H, s), 6.40 (1H, m), 5.21 (1H, s), 3.44 (1H, m), 2.56 (3H, s), 1.10 (6H, d, J=6.3 Hz). ¹³C NMR (100 MHz, CDCl₃) 158.6 (d, J=241 Hz), 153.7, 152.0, 150.3, 149.8, 145.1, 143.9, 136.5 (d, J=11 Hz), 135.8, 134.7, 133.8, 130.7, 129.7, 127.9, 123.7, 123.2, 119.1, 114.7 (d, J=24 Hz), 114.6 (d, J=9 Hz), 113.4 (d, J=22 Hz), 98.4, 88.9, 49.5, 23.8, 23.4. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₄F₄N₅O: 522.1911: found: 522.1898.

TBI-864, 8-Fluoro-5-(4-trifluoromethoxyphenyl)-3-cyclopropylimino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.42 (1H, br. s), 7.63 (1H, dd, J=8.1, 2.4 Hz), 7.58 (2H, d, J=8.1 Hz), 7.42 (2H, d, J=8.1 Hz), 7.34 (1H, m), 7.16 (1H, d, J=8.1 Hz), 6.85 (1H, m), 6.62 (1H, s), 6.35 (1H, dd, J=9.3, 5.4 Hz), 5.48 (1H, s), 2.71 (1H, m), 2.56 (3H, s), 0.88 (2H, m), 0.83 (2H, m). ¹³C NMR (100 MHz, CDCl₃) 158.6 (d, J=242 Hz), 153.9, 152.2, 149.7, 144.9, 144.0, 143.8, 136.5 (d, J=10 Hz), 135.8, 134.5, 133.6, 130.8, 129.9, 128.2, 123.7, 123.3, 119.1, 114.7 (d, J=23 Hz), 114.6 (d, J=10 Hz), 113.4 (d, J=23 Hz), 98.4, 89.2, 33.0, 23.9, 11.4. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₂F₄N₅O: 520.1755; found: 520.1743.

TBI-865, 8-Fluoro-5-(4-(trifluoromethoxyphenyl)-3-cyclohexylimino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.45 (1H, s), 7.66 (1H, dd, J=8.1, 2.1 Hz), 7.59 (2H, d, J=8.1 Hz), 7.40 (2H, d, J=8.1 Hz), 7.36 (1H, m), 7.17 (1H, d, J=8.1 Hz), 6.87 (1H, m), 6.67 (1H, s), 6.43 (1H, 5.17 (1H, s), 3.04 (1H, m), 2.56 (3H, s), 1.73 (2H, m), 1.58 (3H, m), 1.37 (2H, m), 1.16 (3H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 159.8 (d, J=239 Hz), 153.7, 152.1. 150.4, 149.7, 145.1, 143.9, 136.5 (d, J=10 Hz), 135.9, 134.7, 133.9, 130.8, 129.7, 127.9, 123.9, 123.2, 119.1, 114.9 (d, J=23 Hz), 114.6 (d, J=10 Hz), 113.4 (d, J=23 Hz), 98.4, 89.2, 58.2, 33.6, 25.8, 24.7, 23.8. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₂₈F₄N₅O: 562.2224; found: 562.2182.

TBI-866, 8-Fluoro-5-(4-trifluoromethoxyphenyl)-3-(4-methoxycyclohexyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.45 (1H, br. s), 7.67 (1H, br. d, J=7.8 Hz), 7.59 (2H, d, J=8.1 Hz), 7.40 (2H, d, J=8.1 Hz), 7.37 (1H, m), 7.18 (1H, d, J=7.8 Hz), 6.88 (1H, m), 6.68 (1H, s), 6.44 (1H, m), 5.18 (1H, s), 3.36 (3H, s), 3.19 (1H, m), 3.07 (1H, m), 2.57 (3H, s), 2.07 (2H, m), 1.68 (2H, m), 1.43 (2H, m), 1.17 (2H, m). ¹³C NMR (100 MHz, CDCl₃) 158.6 (d, J=239 Hz), 153.8, 151.9, 151.0, 149.8, 144.9, 143.9, 136.5 (d, J=10 Hz), 135.8, 134.5, 133.8, 130.8, 129.7, 127.9, 123.8, 123.3, 119.1, 114.9 (d, J=24 Hz), 114.6 (d, J=10 Hz), 113.5 (d, J=21 Hz), 98.5, 88.9, 78.4, 57.4, 55.8, 31.1, 29.9, 23.8. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₂H₃₀F₄O₅O₂: 592.2271; found: 592.2247.

TBI-898, 7-Methoxy-5-(4-chlorophenyl)-3-(1-methylethyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.44 (1H, d, J=1.5 Hz), 7.70 (2H, d, J=7.8 Hz), 7.67 (1H, m), 7.61 (1H, d, J=9.0 Hz), 7.29 (2H, d, J=7.8 Hz), 7.14 (1H, d, J=8.4 Hz), 6.77 (1H, dd, J=9.0, 2.1 Hz), 6.70 (1H, s), 5.91 (1H, d, J=2.1 Hz), 5.26 (1H, s), 3.70 (3H, s), 3.45 (1H, m), 2.55 (3H, s), 1.09 (6H, d, J=6.3 Hz). ¹³C NMR (100 MHz, CDCl₃) 159.3, 152.9, 150.4, 148.7, 143.5, 143.4, 136.1, 135.7, 134.7, 134.3, 132.6, 131.7, 130.6, 130.3, 129.5, 129.1, 123.1, 109.4, 99.1, 98.9, 89.4, 55.5, 49.3, 23.8, 23.6. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₇ClN₅O: 484.1899; found: 484.1890.

TBI-867, 7-Methoxy-5-(4-chlorophenyl)-3-(4-methoxycyclohexyl)imino-2-(6-methyl-3-pyridyl-amino)-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.43 (1H, br. s), 7.70 (2H, d, J=8.1 Hz), 7.67 (1H, m), 7.61 (1H, d, J=9.0 Hz), 7.29 (2H, d 8.1 Hz), 7.14 (1H, d, J=8.4 Hz), 6.78 (1H, dd, J=9.0, 1.8 Hz), 6.71 (1H, s), 5.94 (1H, 1.8 Hz), 5.24 (1H, s), 3.71 (3H, s), 3.36 (3H, s), 3.18 (1H, m), 3.09 (1H, m), 2.55 (3H, s), 2.07 (2H, m), 1.70 (2H, m), 1.42 (2H, m), 1.17 (2H, ¹³C NMR (100 MHz, CDCl₃) δ: 159.4, 153.0, 151.2, 148.5, 143.5, 143.3, 136.0, 135.9, 134.7, 134.2, 1315, 131.6, 130.7, 130.2, 129.5, 129.1, 123.1, 109.6, 99.2, 98.8, 89.4, 78.5, 57.2, 55.8, 55.5, 31.2, 29.9, 23.8. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₂H₃₃ClN₅O₂: 554.2277: found: 554.2269.

TBI-868, 7-Methoxy-5-(4-chlorophenyl)-3-cyclopropylimino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.40 (1H, d, J=2.1 Hz), 7.70 (2H, d, J=8.7 Hz), 7.64 (1H, dd, J=8.7, 2.1 Hz), 7.61 (1H, d, J=9.0 Hz), 7.31 (2H, d, J=8.7 Hz), 7.14 (1H, d, J=8.7 Hz), 6.76 (1H, dd, J=9.0, 2.4 Hz), 6.65 (1H, s), 190 (1H, d, J=2.4 Hz), 5.53 (1H, s), 3.70 (3H, s), 2.72 (1H, m), 2.54 (3H, s), 0.87 (2H, m), 0.79 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 159.4, 153.1, 152.6, 148.9, 143.6, 143.2, 136.1, 135.7, 134.5, 134.2, 132.8, 131.8, 130.7, 130.4, 129.4, 129.3, 123.1, 109.3, 99.1, 98.9, 89.8, 55.5, 32.8, 23.8, 9.8. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₅ClN₅O: 482.1660; found: 482.1667.

TBI-869, 7-Methoxy-5-(4-chlorophenyl)-3-cyclohexylimino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.44 (1H, br. s), 7.70 (2H, d, J=8.4 Hz), 7.64 (1H, m), 7.61 (1H, m), 7.31 (2H, d, J=8.7 Hz), 7.14 (1H, d, J=7.8 Hz), 6.81 (1H, m), 6.74 (1H, s), 5.96 (1H, br. s), 5.26 (1H, s), 3.70 (3H, s), 3.05 (1H, m), 2.53 (3H, s), 1.72 (2H, m), 1.60 (3H, m), 1.34 (2H, m), 1.16 (3H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 160.2, 153.1, 152.7, 150.7, 143.6, 143.1, 135.9, 135.8, 134.7, 134.3, 132.4, 131.6, 130.6, 130.2, 129.5, 129.4, 123.1, 109.7, 99.2, 98.7, 89.7, 57.7, 55.6, 33.4, 25.7, 24.7, 23.8. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₁ClN₅O: 524.2174; found: 524.2155.

TBI-858, 7-Fluoro-5-(4-trifluoromethoxyphenyl)-3-(1-methylethyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.88 (1H, br. s), 7.82 (2H, m), 7.64 (1H, m), 7.59 (2H, d, J=8.7 Hz), 7.40 (2H, d, J=8.7 Hz), 6.91 (2H, m), 6.87 (1H, s), 6.12 (1H, m), 5.24 (1H, s), 4.03 (3H, s), 3.42 (1H, m), 1.09 (6H, d, J=6.3 Hz). ¹³C NMR (100 MHz, CDCl₃) δ: 161.2 (d, J=246 Hz), 155.5, 150.5, 150.4, 149.9, 142.7, 138.9, 135.5, 134.4, 132.5 (d, J=11.5 Hz), 132.3, 130.7, 129.8 (d, J=9.9 Hz), 124.9, 124.8, 123.8, 116.8, 110.4 (d, J=23.4 Hz), 100.6 (d, J=28.6 Hz), 100.0, 90.0, 53.7, 49.5, 23.5. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₄F₄N₅O₂: 538.1861; found: 538.1833.

TBI-857, 7-Fluoro-5-(4-trifluoromethoxyphenyl)-3-cyclopropylimino-2-(2-methoxy-3-pyridyl-amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.54 (1H, br. s), 7.80 (2H, m), 7.62 (1H, dd, J=8.7, 6.0 Hz), 7.59 (2H, 8.) Hz), 7.42 (2H, d, J=8.1 Hz), 6.90 (2H, m), 6.83 (1H, s), 6.09 (1H, dd, J=7.2, 2.4 Hz), 5.52 (1H, s), 4.01 (3H, s), 2.71 (1H, m), 0.90 (2H, m), 0.84 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 161.2 (d, J=246 Hz), 155.4, 152.4, 150.7, 149.9, 142.5, 139.0, 135.5, 134.2, 132.6 (d, J=11.1 Hz), 132.4, 130.7, 129.6 (d, J=9.6 Hz), 125.0, 124.7, 123.8, 116.8, 110.4 (d, J=23.5 Hz), 100.6 (d, J=28.6 Hz), 100.0, 90.4, 53.7, 33.0, 10.2. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₂F₄N₅O₂: 536.1704; found: 536.1679.

TBI-856, 7-Fluoro-5-(4-trifluoromethoxyphenyl)-3-cyclohexylimino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.94 (1H, br. s), 7.81 (2H, m), 7.63 (1H, dd, J=9.3, 6.3 Hz), 7.60 (2H, d, J=8.7 Hz), 7.40 (2H, d, J=8.7 Hz), 6.90 (2H, m), 6.87 (1H, s), 6.16 (1H, dd, J=10.2, 2.4 Hz), 5.20 (1H, s), 4.03 (3H, s), 3.08 (1H, m), 1.75 (2H, m), 1.58 (3H, m), 1.40 (3H, m), 1.21 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 161.7 (d, J=247 Hz), 155.4, 150.6, 150.5, 149.8, 142.6, 138.7, 135.6, 134.3, 132.4 (d, J=11.5 Hz), 132.3, 130.7, 129.7 (d, J=9.9 Hz), 124.9, 124.5, 123.9, 116.8, 110.4 (d, J=23.4 Hz), 100.5 (d, J=28.6 Hz), 100.0, 90.2, 57.8, 53.7, 33.6, 25.9, 24.3. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₂₈F₄N₅O₂: 578.2174; found: 578.2161.

TBI-855, 7-Fluoro-5-(4-trifluoromethoxyphenyl)-3-(4-tetrahydropyranyl)imino)-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.93 (1H, br. s), 7.83 (2H, m), 7.71 (1H, dd, J=9.3, 6.3 Hz), 7.61 (2H, d, J=8.7 Hz), 7.41 (2H, d, J=8.7 Hz), 6.96 (2H, m), 6.93 (1H, s), 6.18 (1H, m), 5.21 (1H, s), 4.04 (3H, s), 4.01 (2H, m), 3.41 (3H, m), 1.65 (4H, m). ¹³C NMR 100 MHz, CDCl₃) δ: 161.9 (d, J=246 Hz), 155.4, 151.1, 150.1, 150.0, 142.5, 139.0, 135.5, 134.6, 132.4 (d, J=11.1 Hz), 132.2, 130.5, 130.1 (d, J=9.6 Hz), 125.2, 124.7, 123.7, 116.8, 110.8 (d, J=23.5 Hz), 100.7 (d, J=28.6 Hz), 97.5, 89.7, 65.7, 53.9, 53.8, 33.3. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₂₆F₄N₅O₃: 580.1966; found: 580.1930.

TBI-854, 7-Fluoro-5-(4-trifluoromethoxyphenyl)-3-(1-methylethyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.45 (1H, d, J=2.4 Hz), 7.65 (2H, m), 7.59 (2H, d, J=8.7 Hz), 7.40 (2H, d, J=8.7 Hz), 7.16 (1H, d, J=8.1 Hz), 6.88 (1H, m), 6.67 (1H, s), 6.13 (1H, dd, J=10.2, 2.1 Hz), 5.24 (1H, s), 3.43 (1H, m), 2.56 (3H, s), 1.09 (6H, d, J=6.3 Hz). ¹³C NMR (100 MHz, CDCl₃) 161.6 (d, J=246 Hz), 153.5, 150.3, 150.2, 149.9, 144.2, 143.8, 135.5, 134.4, 134.0, 132.4, 132.3 (d, J=11.1 Hz), 130.6, 129.7 (d, J=9.5 Hz), 129.5, 123.7, 123.2, 110.5 (d, J=23.3 Hz), 100.6 (d, J=28.6 Hz), 98.7, 89.8, 49.5, 23.8, 23.5. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₄F₄N₅O: 522.1911; found: 522.1872.

TBI-853, 7-Fluoro-5-(4-trifluoromethoxyphenyl)-3-cyclohexylimino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.45 (1H, d, J=2.7 Hz), 7.66 (2 Ft in), 7.60 (2H, d, J=8.7 Hz), 7.40 (2H, d, J=8.7 Hz), 7.16 (1H, d, J=8.4 Hz), 6.87 (1H, m), 6.66 (1H, s), 6.17 (1H, dd, J=11.2, 2.4 Hz), 5.21 (1H, s), 3.04 (1H, m), 2.56 (3H, s), 1.73 (2H, m), 1.58 (3H, m), 1.37 (2H, m), 1.18 (3H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 161.6 (d, J=246 Hz), 153.5, 150.5, 150.4, 149.9, 144.3, 143.8, 135.7, 134.3, 134.0, 132.3, 132.2 (d, J=11.1 Hz), 130.6, 129.7 (d, J=9.5 Hz), 129.5, 124.0, 123.2, 110.5 (d, J=23.2 Hz), 100.6 (d, J=28.6 Hz), 98.7, 90.1, 58.3, 33.7, 25.8, 24.7, 23.8. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₂₈F₄N₅O: 562.2224; found: 562.2196.

TBI-852, 7-Fluoro-5-(4-trifluoromethoxyphenyl)-3-(4-methoxycyclohexyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.44 (1H, d, J=2.1 Hz), 7.65 (2H, m), 7.59 (2H, d, J=8.4 Hz), 7.39 (2H, d, J=8.4 Hz), 7.16 (1H, d, J=8.1 Hz), 6.89 (1H, m), 6.68 (1H, s), 6.17 (1H, dd, J=11.8, 2.1 Hz), 5.21 (1H, s), 3.35 (3H, s), 3.18 (1H, m), 3.06 (1H, m), 2.56 (3H, s), 2.06 (2H, m), 1.67 (2H, m), 1.38 (2H, m), 1.17 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 161.6 (d, J=246 Hz), 153.6, 151.0, 150.2, 150.0, 144.2, 143.8, 135.5, 134.4, 133.9, 132.3, 132.2 (d, J=11.1 Hz), 130.6, 129.8 (d, J=9.5 Hz), 129.5, 123.8, 123.2, 110.6 (d, J=23.2 Hz), 100.6 (d, J=28.6 Hz), 98.8, 89.8, 78.4, 57.5, 55.8, 31.2, 29.9, 23.8. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₂H₃₀F₄N₅O₂: 592.2271; found: 592.2255.

TBI-1051, 5-(4-Chlorophenyl)-3-(1-methylethyl)imino-2-(pyrimidin-2-yl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 9.76 (1H, hr s), 8.56 (2H, d, J=4.5 Hz), 8.49 (s, 1H), 7.77 (1H, d, J=6.9 Hz), 7.71 (2H, m), 7.32 (2H, m), 7.17 (2H, m), 6.83 (1H, m), 6.44 (1H, d, J=6.9 Hz), 5.28 (1H, s), 3.47 (1H, m), 1.10 (6H, d, J=6.0 Hz). ¹³C NMR (100 MHz, CDCl₃) δ: 159.3, 157.9, 151.8, 150.1, 140.2, 136.0, 135.7, 135.0, 132.0, 131.7, 130.5, 128.8, 128.3, 122.8, 113.7, 113.5, 108.4, 89.0, 49.4, 23.6. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₅H₂₂ClN₆: 441.1589: found: 441.1589.

TBI-1052, 5-(4-Fluorophenyl)-3-(1-methylethyl)imino-2-(3-nitro-2-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 12.23 (1H, hr y), 8.73 (1H, s), 8.66 (1H, d, J=3.9 Hz), 8.56 (1H, d, J=8.1 Hz), 7.76 (1H, 5.1 Hz), 7.43 (2H, m), 7.36 (2H, m), 7.17 (1H, m), 6.95 (1H, dd, J=7.8, 4.5 Hz), 6.44 (1H, m), 5.28 (1H, s), 3.48 (1H, m), 1.15 (6H, d, J=6.3 Hz). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, J=247.7 Hz), 154.3, 151.9, 150.6, 148.8, 140.4, 135.6, 135.5, 135.1, 133.2, 132.4, 130.9, 130.8, 129.0, 128.8, 128.5, 122.9, 118.6 (d, J=23.1 Hz), 114.8, 113.8, 111.5, 89.1, 49.5, 23.5. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₆H₂₂FN₆O₂: 469.1783; found: 469.1781.

TBI-1053, 5-(4-Fluorophenyl)-3-(1-methylethyl)imino-2-(pyrimidin-2-yl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 9.75 (1H, br s), 8.54 (2H, d, J=4.8 Hz), 8.48 (1H, s), 7.77 (1H, s), 7.42 (2H, m), 7.35 (2H, m), 7.16 (2H, s), 6.81 (1H, m), 6.45 (1H, s), 5.25 (1H, s), 3.44 (1H, m), 1.08 (6H, d, J=4.8 Hz). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, J=248.9 Hz), 159.4, 157.8, 151.8, 150.2, 1401, 135.3, 133.3, 132.2, 131.3, 130.9, 130.8, 130.2, 128.8, 128.3, 122.8, 118.5 (d, J=22.6 Hz), 113.8, 113.5, 108.4, 89.0, 49.4, 23.5. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₅H₂₂FN₆: 425.1884: found: 425.1892.

TBI-1054, 5-(4-Fluorophenyl)-3-(1-methylethyl)imino-2-(2-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.39 (1H, d, J=3.0 Hz), 8.28 (1H, s), 7.77 (1H, d, J=6.9 Hz), 7.58 (1H, m), 7.42 (2H, m), 7.36 (2H, m), 7.16 (2H, m), 6.99 (1H, d, J=8.1 Hz), 6.86 (1H, m), 6.46 (1H, J=7.8 Hz), 5.26 (1H, s), 3.45 (1H, m), 1.09 (6H, d, J=6.0 Hz). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, J=249.2 Hz), 154.1, 151.8, 150.6, 148.2, 141.0, 137.1, 135.8, 135.1, 133.5, 132.0, 131.0, 130.9, 128.6, 127.8, 122.7, 118.4 (d, J=12.9 Hz), 116.3, 113.8, 112.8, 105.4, 89.0, 49.3, 23.6. HRMS m/z [M+H]⁺ calcd for C₂₆H₂₃FN₅: 424.1932: found: 424.1929.

TBI-1055, 5-(4-Fluorophenyl)-3-(1-methylethyl)imino-2-(pyrazin-2-yl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.44 (1H, s), 8.29 (2H, m), 8.05 (1H, d, J=2.7 Hz), 7.78 (1H, dd, J=6.6, 2.7 Hz), 7.43 (2H, m), 7.35 (2H, m), 7.18 (2H, m), 6.45 (1H, dd, J=7.2, 2.1 Hz), 5.26 (1H, s), 3.45 (1H, m), 1.09 (6H, d, 6.3 Hz). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, J=249.3 Hz), 151.4, 151.1, 150.5, 141.6, 140.0, 136.3, 135.7, 135.5, 135.4, 133.3, 132.0, 130.9, 130.8, 128.8, 128.3, 128.2, 123.0, 118.5 (d, J=23.1 Hz), 113.9, 107.4, 88.9, 49.3, 23.5. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₅H₂₂FN₆: 425.1884; found: 425.1883.

TBI-1057, 5-(4-Fluorophenyl)-3-(1-methylethyl)imino-2-(3-cyano-2-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 10.29 (1H, br s), 8.59 (1H, s), 8.53 (1H, dd, J=4.8, 1.8 Hz), 7.80 (2H, m), 7.45 (2H, m), 7.38 (2H, m), 7.22 (2H, m), 6.82 (1H, dd, J=7.5, 5.1 Hz), 6.53 (1H, d, J=7.8 Hz), 5.31 (1H, s), 3.48 (1H, m), 1.16 (6H, d, J=6.3 Hz). ¹³C NMR (100 MHz, CDCl₃) δ: 162.9 (d, J=249.3 Hz), 156.7, 151.4, 150.8, 141.2, 140.5, 136.3, 135.8, 1332, 131.4, 130.7, 130.6, 128.9, 128.3, 123.6, 118.5 (d, J=22.6 Hz), 116.5, 114.2, 108.3, 97.6, 88.4, 48.4, 23.1. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₂FN₆: 448.1884; found: 449.1890.

TBI-1064, 8-Cyano-5-(4-fluorophenyl)-3-(1-methylethyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 7.90 (1H, s), 7.83 (1H, m), 7.44 (2H, m), 7.32 (4H, m), 6.94 (1H, m), 6.84 (1H, s), 6.45 (1H, d, J=8.4 Hz), 5.34 (1H, s), 4.03 (3H, s), 3.47 (1H, m), 1.11 (6H, d, J=2.4 Hz). ¹³C NMR (100 MHz, CDCl₃) δ: 163.0 (d, J=249.7 Hz), 155.7, 152.8, 150.2, 143.7, 139.7, 135.4, 135.0, 134.4, 132.6, 131.9, 130.7, 130.6, 130.0, 125.6, 124.3, 118.9, 118.8 (d, J=15.1 Hz), 116.8, 114.5, 105.5, 99.6, 91.2, 53.8, 49.8, 23.5, 21.1. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₄FN₆O: 479.1990; found: 479.1980.

TBI-1065, 8-Cyano-5-(4-fluorophenyl)-3-(4-methyoxycyclohexyl)imino-2-(2-methoxy-3-pyrid-yl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 7.92 (1H, s), 7.86 (1H, d, J=4.5 Hz), 7.82 (1H, d, J=8.1 Hz), 7.45 (2H, m), 7.33 (3H, m), 6.95 (1H, dd, J=7.2, 5.4 Hz), 6.87 (1H, s), 6.49 (1H, d, J=8.4 Hz), 5.33 (1H, s), 4.04 (3H, s), 3.37 (3H, s), 3.25 (1H, m), 3.15 (1H, m), 2.09 (2H, m), 1.70 (2H, m), 1.47 (2H, m), 1.24 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 163.0 (d, J=250.9 Hz), 155.5, 152.7, 150.9, 143.5, 139.5, 135.4, 134.8, 134.4, 132.5, 132.0, 130.6, 130.5, 130.1, 125.3, 124.2, 118.9, 118.7 (d, J=14.6 Hz), 116.9, 114.5, 105.6, 99.7, 91.1, 57.2, 55.8, 53.8, 30.7, 29.3. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₂H₃₀FN₆O₂: 549.2409: found: 549.2393.

TBI-1066, 8-Cyano-5-(4-fluorophenyl)-3-(4-tetrahydropyranyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 9.02 (1H, br, s), 7.93 (1H, d, J=1.5 Hz), 7.84 (2 m), 7.46 (2H, m), 7.34 (3H, m), 6.95 (1H, dd, J=7.5, 5.4 Hz), 6.90 (1H, s), 6.49 (1H, d, J=8.4 Hz), 5.31 (1H, 0.4.05 (3H, s), 3.99 (2H, m), 3.50 (3H, m), 1.60 (4H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 177.4, 163.1 (d, J=250.9 Hz), 155.4, 152.5, 150.8, 143.4, 140.5, 139.5, 135.4, 134.7, 134.6, 133.7, 132.5, 132.1, 130.8, 130.6, 130.5, 130.2, 130.1, 130.0, 125.1, 125.0, 124.3, 118.8 (d, J=22.6 Hz), 116.9, 116.2, 114.6, 105.8, 101.1, 100.2, 99.9, 90.8, 65.5, 53.8, 53.7, 33.3.

TBI-1067, 8-Cyano-5-(4-fluorophenyl)-3-(1-methylethyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.46 (1H, d, J=2.4 Hz), 7.89 (1H, s), 7.66 (1H, dd, J=8.4, 2.7 Hz), 7.45 (2H, m), 7.31 (3H, m), 7.19 (1H, d, J=8.1 Hz), 6.64 (1H, s), 6.46 (1H, d, J=8.7 Hz), 5.34 (1H, s), 3.47 (1H, m), 2.59 (3H, s), 1.10 (6H, d, J=6.3 Hz). ¹³C NMR (100 MHz, CDCl₃) δ: 163.0 (d, J=250.1 Hz), 154.1, 152.5, 150.0, 145.3, 144.0, 135.4, 134.8, 134.5, 133.5, 132.6, 132.0, 130.6, 130.5, 130.0, 123.3, 118.8 (d, J=22.6 Hz), 118.7, 114.5, 105.6, 98.5, 91.0, 49.8, 23.9, 23.5. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₄FN₆: 463.2041; found: 463.2053.

TBI-1068, 8-Cyano-5-(4-fluorophenyl)-3-(4-methyoxycyclohexyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.45 (1H, s), 7.90 (1H, s), 7.65H, d, J=8.7 Hz), 7.44 (2H, m), 7.32 (3H, m), 7.19 (1H, d, J=8.1 Hz), 6.64 (1H, s,), 6.49 (1H, d, J=8.4 Hz), 5.32 (1H, s), 3.36 (3H, s), 3.20 (1H, m), 3.10 (1H, m), 2.57 (3H, s), 2.08 (2H, m), 1.67 (2H, m), 1.45 (2H, m), 1.21 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 163.0 (d, J=251.3 Hz), 154.2, 152.4, 150.8, 145.2, 144.0, 135.4, 134.7, 134.5, 133.4, 132.5, 132.0, 130.6, 130.5, 130.0, 129.9, 123.3, 118.8 (d, J=22.6 Hz), 118.9, 114.6, 105.7, 98.6, 91.0, 78.3, 57.7, 55.8, 31.2, 29.8, 23.9. HRMS (ESI-TOF⁺): calcd for C₃₂H₃₀FN₆O: 533.2460; found: 533.2446.

TBI-1075, 5-(4-Chlorophenyl)-3-(1-methylethyl)imino-2-(3-cyano-2-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 10.29 (1H, br s), 8.58 (1H, s), 8.52 (1H, d, J=3.3 Hz), 7.81 (2H, m), 7.73 (2H, d, J=8.4 Hz), 7.33 (2H, d, J=8.4 Hz), 7.21 (2H, m), 6.82 (1H, dd, J=7.2, 4.8 Hz), 6.51 (1H, d, J=8.1 Hz), 5.32 (1H, s), 3.49 (1H, m), 1.16 (6H, d, J=6.0 Hz). ¹³C NMR (100 MHz, CDCl₃) δ: 156.5, 152.1, 151.3, 150.8, 141.2, 140.4, 136.2, 136.0, 135.7, 135.5, 131.7, 131.3, 130.2, 128.9, 128.3, 123.6, 116.4, 114.3, 114.2, 108.3, 97.5, 88.5, 48.5, 23.2. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₂ClN₆: 465.1589; found: 465.1583.

TBI-1076, 5-(4-Chlorophenyl)-3-(1-methylethyl)imino-2-(2-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.38 (1H, d, J=4.5 Hz), 0.27 (1H, s), 7.75 (1H, d, J=8.1 Hz), 7.70 (2H, d, J=8.7 Hz), 7.57 (1H, m), 7.31 (2H, d, J=8.7 Hz), 7.15 (2H, m), 6.98 (1H, d, J=8.7 Hz), 6.85 (1H, m), 6.43 (1H, d, 7.5 Hz), 526 (1H, s), 3.45 (1H, m), 1.08 (6H, d, J=6.0 Hz). ¹³C NMR (100 MHz, CDCl₃) δ: 154.1, 151.7, 150.5, 148.2, 141.0, 137.1, 136.1, 135.7, 135.6, 134.8, 131.7, 131.6, 130.5, 128.6, 127.8, 122.8, 116.3, 113.7, 112.8, 105.4, 89.0, 49.3, 23.6. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₆H₂₃ClN₅: 440.1636; found: 440.1647.

TBI-1077, 5-(4-Chlorophenyl)-3-(1-methylethyl)imino-2-(pyrazin-2-yl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.43 (1H, s), 8.29 (2H, m), 8.05 (1H, d, J=2.4 Hz), 7.77 (1H, d, J=6.9 Hz), 7.71 (2H, d, J=8.1 Hz), 7.31 (2H, d, J=8.1 Hz), 7.17 (2H, m), 6.45 (1H, d, J=7.8 Hz), 5.28 (1H, s), 3.47 (1H, m), 1.11 (6H, d, J=6.3 Hz). ¹³C NMR (100 MHz, CDCl₃) δ: 151.4, 151.0, 150.4, 141.6, 140.0, 136.4, 135.9, 135.8, 135.5, 135.1, 131.7, 130.4, 128.9, 128.4, 123.0, 113.8, 107.5, 88.9, 49.3, 23.6. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₅H₂₂ClN₆: 441.1589: found: 441.1567.

TBI-1078, 5-(4-Fluorophenyl)-(4-ethoxycyclohexyl)imino-2-(2-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 9.20 (1H, br s), 8.38 (1H, d, J=3.6 Hz), 8.26 (1H, s), 7.76 (1H, dd, J=7.2, 2.1 Hz), 7.57 (1H, m), 7.41 (2H, m), 7.34 (2H, m), 7.16 (2H, m), 6.97 (1H, d, J=8.4 Hz), 6.85 (1H, m), 6.48 (1H, dd, J=7.2, 1.8 Hz), 5.23 (1H, s), 3.36 (3H, s), 3.19 (1H, m), 3.07 (1H, m), 2.06 (2H, m), 1.68 (2H, m), 1.41 (2H, m), 1.21 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, J=249.3 Hz), 154.0, 151.6, 151.4, 148.2, 140.9, 137.1, 135.8, 135.1, 133.4, 131.9, 130.9, 130.8, 128.6, 127.9, 122.8, 118.4 (d, J=23.0 Hz), 116.3, 113.8, 112.8, 105.4, 89.0, 78.5, 57.3, 55.8, 31.1, 29.9. HRMS (EST-TOO: m/z [M+H]⁺ calcd for C₃₀H₂₉FN₅O: 494.2351; found: 494.2345.

TBI-1079, 5-(4-Fluorophenyl)-3-(4-methoxycyclohexyl)imino-2-(pyrazin-2-yl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.44 (1H, s), 8.29 (2H, s), 8.06 (1H, s), 7.78 (1H, J=7.8 Hz), 7.42 (2H, m), 7.35 (2H, m), 7.19 (2H, m), 6.49 (1H, d, J=7.8 Hz), 5.24 (1H, s), 3.37 (3H, s), 3.21 (1H, m), 3.08 (1H, m), 2.07 (2H, m), 1.69 (2H, m), 1.43 (2H, m), 1.22 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, J=250.5 Hz), 151.2, 151.0, 141.6, 139.9, 136.3, 135.8, 135.3, 133.2, 131.9, 130.8, 130.7, 128.9, 128.5, 123.1, 118.4 (d, J=23.1 Hz), 113.9, 107.5, 88.9, 78.4, 57.2, 55.8, 31.1, 29.9. HRMS ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₈FN₆O: 495.2303: found: 495.2293.

TBI-1080, 5-(4-Fluorophenyl)-3-(4-methoxycyclohexyl)imino-2-(pyrimidin-2-yl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 9.69 (1H, br s), 8.54 (2H, d, J=4.8 Hz), 8.49 (1H, s), 7.77 (1H, d, J=8.1 Hz), 7.41 (2H, m), 7.34 (2H, m), 7.17 (2 D, m), 6.82 (1H, m), 7.47 (1H, d, J=8.1 Hz), 5.24 (1H, s), 3.37 (3H, s), 3.21 (1H, m), 3.08 (1H, m), 2.07 (2H, m), 1.69 (2H, m), 1.43 (2H, m), 1.22 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, J=249.7 Hz), 159.3, 157.9, 151.7, 151.0, 140.1, 135.7, 135.3, 133.3, 132.1, 130.9, 130.8, 128.8, 128.4, 122.8, 118.4 (d, J=22.6 Hz), 113.8, 113.5, 108.5, 89.0, 78.5, 57.4, 55.8, 31.1, 29.9. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₈FN₆O: 495.2303; found: 495.2306.

TBI-1082, 5-(4-Fluorophenyl)-3-(4-methoxycyclohexyl)imino-2-(3-cyano-2-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 10.33 (1H, br s), 8.59 (1H, s), 8.53 (1H, dd, J=4.5, 1.2 Hz), 7.80 (2 dd, J=7.5, 1.8 Hz), 7.43 (2H, m), 7.36 (2H, m), 7.21 (2H, m), 6.84 (1H, dd, J=7.5, 4.8 Hz), 6.52 (1H, d, J=8.7 Hz), 5.27 (1H, s), 3.35 (3H, s), 3.26 (1H, m), 3.15 (1H, m), 2.07 (2H, m), 1.73 (2H, m), 1.47 (2H, m), 1.24 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 162.9 (d, J=250.2 Hz), 155.9, 152.1, 151.4, 151.1, 141.2, 139.9, 136.0, 135.6, 133.1, 131.7, 130.7, 130.6, 129.0, 128.5, 123.4, 118.5 (d, J=22.6 Hz), 116.2, 114.5, 114.1, 108.7, 96.8, 88.6, 77.9, 56.0, 55.8, 30.4, 29.2. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₂₈FN₆O: 519.2303; found: 519.2338.

TBI-1083, 5-(4-Fluorophenyl)-3-(4-methoxycyclohexyl)imino-2-(3-nitro-2-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 12.20 (1H, br s), 8.73 (1H, s), 8.66 (1H, m), 8.56 (1H, d, J=8.1 Hz), 7.77 (1H, m), 7.42 (2H, m), 7.35 (2H, m), 7.18 (2H, m), 6.95 (1H, dd, J=7.8, 4.5 Hz), 6.47 (1H, m), 5.25 (1H, s), 3.36 (3H, s), 3.27 (1H, m), 3.14 (1H, m), 2.11 (2H, m), 1.72 (2H, m), 1.54 (2H, m), 1.24 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, J=249.3 Hz), 154.3, 151.8, 151.3, 148.7, 140.2, 135.7, 135.5, 135.2, 133.1, 132.4, 130.9, 130.8, 129.0, 128.9, 122.9, 118.5 (d, J=22.6 Hz), 114.8, 113.9, 111.6, 89.1, 78.2, 56.9, 55.8, 30.7, 29.4. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₂₈FN₆O₃: 539.2201; found: 539.2204.

TBI-1084, 5-(4-Fluorophenyl)-3-(4-tetrahydropyranyl)imino-2-pyrimidin-2-yl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 9.70 (1H, br s), 8.56 (2H, d, J=4.8 Hz), 8.53 (1H, s), 7.79 (1H, d, J=7.2 Hz), 7.44 (2H, m), 7.35 (2H, m), 7.19 (2H, m), 6.83 (1H, m), 6.48 (1H, J=7.2 Hz), 5.23 (1H, s), 3.98 (2H, m), 3.41 (3H, m), 1.64 (4H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, J=249.3 Hz), 159.3, 157.9, 151.5, 151.0, 140.1, 135.7, 135.4, 133.3, 132.0, 130.9, 130.8, 128.9, 128.4, 123.0, 118.5 (d, J=22.7 Hz), 113.9, 113.6, 108.5, 88.9, 66.0, 54.3, 33.3. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₄FN₆O: 467.1990; found: 467.1980.

TBI-1085, 5-(4-Fluorophenyl)-3-(4-tetrahydropyranyl)imino-2-(pyrazin-2-yl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 9.50 (1H, hr s), 8.47 (1H, s), 8.30 (2H, m), 8.06 (1H, d, J=2.4 Hz), 7.79 (1H, d, J=9.0 Hz), 7.44 (2H, m), 7.35 (2H, m), 7.20 (2H, m), 6.49 (1H, d, J=9.0 Hz), 5.23 (1H, s), 3.98 (2H, m), 3.41 (3H, m), 1.64 (4H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 162.9 (d, J=249.7 Hz), 151.2, 150.9, 141.6, 139.9, 136.3, 135.7, 135.5, 133.2, 131.9, 130.8, 130.7, 129.0, 128.6, 123.2, 118.5 (d, J=22.6 Hz), 114.0, 107.6, 88.7, 66.1, 54.2, 33.4. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₄FN₆O: 467.1990; found: 467.1979.

TBI-1086, 5-(4-Fluorophenyl)-3-(4-tetrahydropyranyl)imino-2-(3-cyano-2-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 10.38 (1H, br s), 8.63 (1H, s), 8.55 (1H, d, J=7.2 Hz), 7.82 (2H, m), 7.44 (2H, m), 7.36 (2H, m), 7.21 (2H, m), 6.88 (1H, m), 6.50 (1H, d, J=7.2 Hz), 5.25 (1H, s), 4.03 (2H, m), 3.47 (3H, m), 1.69 (4H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 162.9 (d, J=249.7 Hz), 155.3, 152.1, 151.2, 151.1, 141.3, 139.6, 135.9, 135.7, 133.2, 131.9, 130.8, 130.7, 129.0, 128.7, 123.3, 118.6 (d, J=22.7 Hz), 115.9, 114.8, 114.1, 109.0, 96.5, 88.6, 66.5, 53.0, 33.1. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₄FN₆O: 491.1990; found: 491.1981.

TBI-1087, 5-(4-Fluorophenyl)-3-(4-tetrahydropyranyl)imino-2-(2-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 9.25 (1H, br s), 8.39 (1H, d, J=3.3 Hz), 8.34 (1H, s), 7.78 (1H, dd, J=7.5, 1.8 Hz), 7.58 (1H, m), 7.43 (2H, m), 7.35 (2H, m), 7.18 (2H, m), 6.96 (1H, d, J=8.4 Hz), 6.86 (1H, m), 6.48 (1H, dd, J=7.5, 1.8 Hz), 5.23 (1H, s), 3.96 (2H, m), 3.38 (3H, m), 1.63 (4H, m). ¹³C NMR (100 MHz, CDCl₃) 6; 162.8 (d, J=249.3 Hz), 154.0, 151.5, 151.3, 148.2, 140.9, 137.2, 135.8, 135.3, 133.4, 131.8, 130.9, 130.8, 128.7, 128.0, 123.0, 118.4 (d, J=22.6 Hz), 116.4, 113.9, 112.9, 105.6, 88.8, 66.1, 54.1, 33.4. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₅FN₅O: 466.2038; found: 466.2022.

TBI-1088, 5-(4-Fluorophenyl)-3-(4-tetrahydropyranyl)imino-2-(3-nitro-2-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 12.20 (1H, s), 8.78 (1H, s), 8.67 (1H, m), 8.57 (1H, d, J=8.1 Hz), 7.79 (1H, m), 7.44 (2H, m), 7.37 (2H, m), 7.20 (2H, m), 6.97 (1H, m), 6.48 (1H, 5.25 (1H, s), 4.06 (2H, m), 3.50 (3H, m), 1.71 (4H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 162.9 (d, J=249.3 Hz), 154.3, 151.7, 151.4, 148.7, 140.2, 135.7, 135.6, 135.2, 133.2, 132.3, 130.8, 130.7, 129.1, 129.0, 123.1, 118.6 (d, J=22.7 Hz), 115.0, 113.9, 111.7, 89.0, 65.5, 53.5, 33.2. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₄FN₆O₃: 511.1888; found: 511.1884.

TBI-1090, 5-(4-Chlorophenyl)-3-(4-methoxycyclohexyl)imino-2-(pyrimidin-2-yl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 9.68 (1H, br s), 8.54 (2H, d, J=4.8 Hz), 8.48 (1H, s), 7.77 (1H, m), 7.69 (2H, d, J=8.4 Hz), 7.29 (2H, d, J=8.4 Hz), 7.16 (2H, m), 6.81 (1H, m), 6.45 (1H, m), 5.25 (1H, s), 3.36 (3H, s), 3.19 (1H, m), 3.090H, m), 2.06 (2H, m), 1.64 (2H, m), 1.43 (2H, m), 1.18 (2H, m); ¹³C NMR (100 MHz, CDCl₃) δ: 159.3, 157.9, 151.7, 150.9, 140.1, 135.8, 135.7, 135.0, 131.9, 131.6, 130.4, 128.9, 128.4, 122.9, 113.8, 113.5, 108.5, 89.0, 78.5, 57.3, 55.8, 31.1, 29.8; HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₈ClN₆O: 511.2008; found: 511.1993.

TBI-1091, 5-(4-Chlorophenyl)-3-(4-methoxycyclohexyl)imino-2-(pyrazin-2-yl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.44 (1H, s), 8.29 (2H, s), 8.06 (1H, s), 7.79 (1H, dd, J=5.1, 3.3 Hz), 7.71 (2H, d, J=7.8 Hz), 7.30 (2H, d, J=7.8 Hz), 7.19 (2H, m), 6.48 (1H, dd, J=5.1, 3.3 Hz), 5.26 (1H, s), 3.37 (3H, s), 3.21 (1H, m), 3.11 (1H, m), 2.08 (2H, m), 1.68 (2H, m), 1.44 (2H, m), 1.22 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 151.3, 151.1, 150.9, 141.6, 139.9, 136.3, 135.9, 135.8, 135.6, 135.1, 131.8, 131.6, 1303, 128.9, 128.5, 123.1, 113.9, 107.5, 88.9, 78.4, 57.1, 55.8, 31.1, 29.8. HRMS (ESI-TOF+): m/z [M+H]⁺ calcd for C₂₉H₂₈ClN₆O: 511.2008: found: 511.1977.

TBI-1092, 5-(4-Fluorophenyl)-3-(1-methylethyl)imino-2-(2-methoxy-6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 7.70 (2H, m), 7.42 (2H, m), 7.34 (2H, m), 7.14 (2H, m), 6.81 (1H, s), 6.73 (1H, d, J=7.5 Hz), 6.44 (1H, d, J=7.5 Hz), 5.26 (1H, s), 4.00 (3H, s), 3.44 (1H, m), 2.44 (3H, s), 1.10 (6H, d, J=6.3 Hz). ¹³C NMR (100 MHz, CDCl₃) δ: 162.8 (d, J=249.3 Hz), 155.1, 151.3, 150.8, 148.6, 143.5, 135.7, 135.0, 133.6, 131.7, 130.9, 130.8, 128.1, 127.3, 126.7, 122.8, 121.6, 118.4 (d, J=22.7 Hz), 115.4, 113.8, 99.3, 89.2, 63.7, 53.5, 49.3, 23.6. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₇FN₅O: 468.2194: found: 468.2188.

TBI-1220, 5-(4-Acetamidophenyl)-3-(1-methylethyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 7.90 (2H, d, J=7.8 Hz), 7.82 (2H, m), 7.69 (1H, d, J=6.0 Hz), 7.28 (2H, m), 7.13 (2H, m), 6.91 (2H, m), 6.48 (1H, d, J=7.8 Hz), 5.34 (1H, s), 4.03 (3H, s), 3.45 (1H, m), 2.29 (1H, s), 1.15 (6H, d, J=6.0 Hz). ¹³C NMR (100 MHz, CDCl₃) δ: 168.6, 155.5, 151.2, 150.7, 142.9, 139.1, 138.8, 135.6, 135.0, 132.9, 132.0, 129.5, 128.0, 127.6, 124.9, 124.8, 122.8, 121.8, 116.8, 114.1, 100.1, 89.2, 53.7, 49.2, 24.7, 23.5. HRMS (ESI-TOF⁺); m/z [M+H]⁺ calcd for C₂₉H₂₉N₆O₂: 492.2274; found: 492.2254.

TBI-1221, 5-(4-Acetamidophenyl)-3-cyclopropylimino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) (2H, d, J=8.4 Hz), 7.81 (3H, m), 7.66 (1H, d, J=5.8 Hz), 7.29 (2H, d, J=8.7 Hz), 7.12 (1H, m), 6.87 (1H, s), 6.45 (1H, d, J=7.8 Hz), 5.6 (1H, s), 4.00 (3H, s), 2.72 (1H, s), 2.26 (3H, s), 0.85 (4 m). ¹³C NMR (100 MHz, CDCl₃) 0:168.7, 155.6, 152.7, 151.1, 147.4, 142.5, 139.1, 135.9, 134.9, 132.8, 132.0, 129.4, 128.1, 127.8, 125.5, 124.6, 123.0, 121.9, 116.8, 114.2, 100.3, 89.7, 53.7, 32.5, 24.7. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₇N₆O₂: 490.2117; found: 490.2088.

TBI-1222, 5-(4-Acetamidophenyl)-3-(4-methoxycyclohexyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 10.14 (1H, s), 9.04 (1H, s), 8.18 (2H, d, J=7.8 Hz), 8.09 (2H, m), 7.76 (1H, d, J=8.4 Hz), 7.60 (2H, m), 7.25 (2H, m), 7.08 (1H, d, J=8.4 Hz), 6.95 (1H, m), 6.65 (1H, s), 5.87 (1H, s), 3.90 (3H, s), 3.71 (1H, m), 3.29 (3H, s), 3.19 (1H, m), 2.33 (3H, s), 2.10 (2H, m), 1.60 (2H, m), 1.25 (2H, m), 1.09 (2H, ¹³C NMR (100 MHz, CDCl₃) δ: 169.6, 158.4, 151.5, 145.8, 144.6, 141.7, 141.5, 138.8, 135.5, 135.3, 131.3, 130.2, 130.0, 129.8, 127.5, 127.3, 122.1, 121.7, 117.5, 105.7, 89.7, 55.9, 54.3, 53.6, 29.9, 28.7, 24.7. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₃H₃₅N₆O₃: 562.2692; found: 562.2742.

TBI-1223, 5-(4-Acetamidophenyl)-3-cyclohexylimino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 7.91 (2H, d, J=8.1 Hz), 7.81 (2H, n), 7.70 (1H, d, J=7.8 Hz), 7.27 (2H, m), 7.14 (2H, m), 6.91 (2H, m), 6.52 (1H, d, J=7.8 Hz), 5.35 (1H, s), 4.02 (3H, s), 3.15 (1H, m), 2.28 (3H, s), 1.47 (10H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 168.6, 155.5, 151.0, 150.7, 142.8, 139.2, 138.8, 135.8, 135.0, 132.8, 131.9, 129.3, 128.1, 127.7, 124.9, 122.9, 121.7, 116.8, 114.2, 100.4, 89.4, 56.9, 53.7, 33.3, 25.9, 24.7, 24.2. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₂H₃₃N₆O₂: 532.2587; found: 532.2576.

TBI-1224, 5-(4-Acetamidophenyl)-3-(4-tetrahydropyranyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 10.36 (1H, s), 9.70 (1H, s), 8.69 (1H, s), 8.29 (2H, d, J=8.1 Hz), 8.16 (1H, d, J=7.5 Hz), 7.85 (1H, m), 7.67 (2H, m), 7.38 (1H, s), 7.18 (2H, d, J=8.1 Hz), 5.93 (1H, s), 3.90 (2H, m), 3.49 (1H, m), 3.26 (2H, m), 2.62 (3H, s), 2.35 (3H, s), 2.11 (2H, m), 1.83 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 170.1, 151.1, 145.4, 142.3, 139.3. 135.3, 132.9, 132.3, 130.4, 130.0, 129.8, 127.8, 127.4, 124.6, 121.9, 117.2, 105.9, 90.3, 66.0, 52.0, 31.0, 24.7. HRMS (ESI-TOF⁺): m/z. [M+H]⁺ calcd for C₃₁H₃₁N₆O₂: 518.2430; found: 518.2472.

TBI-1225, 5-(4-Acetamidophenyl)-3-(4-tetrahydropyranyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 7.85 (4H, m), 7.71 (1H, d, J=7.2 Hz), 7.61 (1H, m), 7.30 (1H, s), 7.16 (2H, m), 6.98 (1H, s), 6.92 (1H, m), 6.52 (1H, d, J=7.2 Hz), 5.31 (1H, s), 4.04 (3H, s), 3.98 (1H, m), 3.49 (4H, m), 2.29 (3H, s), 1.65 (4H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 168.9, 155.6, 151.5, 151.0, 142.8, 139.6, 139.0, 136.0, 135.5, 133.0, 128.5, 128.2, 125.0, 123.4, 122.0, 117.1, 114.6, 100.8, 89.2, 65.8, 54.0, 53.3, 33.4, 25.0. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₁N₆O₃: 534.2379; found: 534.2350.

TBI-1227, 5-(4-Acetamidophenyl)-3-dimethoxyisopropyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 7.85 (4H, m), 7.72 (2H, d, J=6.9 Hz), 7.28 (1H, s), 7.17 (2H, m), 6.95 (1H, s), 6.90 (1H, m), 6.53 (1H, d, J=7.5 Hz), 5.53 (1H, s), 4.01 (3H, s), 3.72 (1H, m), 3.55 (2H, m), 3.39 (2H, m), 3.27 (6H, s), 2.27 (3H, s). ¹³C NMR (100 MHz, CDCl₃) 168.6, 155.7, 153.5, 142.6, 139.5, 132.5, 131.7, 129.2, 128.3, 125.8, 124.6, 123.3, 121.8, 116.9, 114.5, 100.8, 90.1, 56.2, 58.3, 53.6, 24.7. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₃N₆O₄: 552.2485; found: 552.2474.

TBI-1228, 5-(4-Acetamidophenyl)-3-(1-methylethyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.45 (1H, s), 7.90 (2H, d, J=8.1 Hz), 7.68 (2H, m), 7.28 (2H, m), 7.14 (3H, m), 6.73 (1H, s), 6.50 (1H, d, J=7.8 Hz), 5.34 (1H, s), 3.45 (1H, m), 2.56 (3H, s), 2.28 (3H, s), 1.08 (6H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 168.8, 153.3, 150.6, 144.0, 143.7, 139.5, 135.9, 135.1, 134.2, 132.6, 131.6, 129.6, 129.2, 128.2, 127.9, 123.3, 121.7, 123.3, 121.7, 114.4, 89.1, 49.0, 24.7, 23.7, 23.3. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₉N₆O: 476.2325; found: 476.237.

TBI-1229, 5-(4-Acetamidophenyl)-3-(4-methoxycyclohexyl)imino)-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.44 (1H, s), 7.88 (2H, d, J=8.1 Hz), 7.68 (2H, m), 7.28 (2H, m), 7.16 (3H, m), 6.72 (1H, s), 6.53 (1H, d, J=6.3 Hz), 5.30 (1H, s), 3.36 (3H, s), 3.19 (1H, m), 3.09 (1H, m), 2.56 (3 s), 2.30 (3H, s), 2.06 (2H, m), 1.69 (2H, m), 1.41 (2H, m), 1.18 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 168.7, 153.3, 151.3, 150.8, 144.2, 143.7, 139.2, 135.6, 135.1, 134.1, 132.7, 131.7, 129.4, 128.1, 127.6, 123.3, 122.8, 121.7, 114.2, 98.9, 89.0, 57.3, 55.9, 31.2, 30.0, 24.8, 23.8. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₃H₃₅N₆O₂: 546.2743; found: 546.2793.

TBI-1230, 5-(4-Acetamidophenyl)-3-cyclopropylimino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.41 (1H, s), 7.90 (2H, s), 7.64 (2H, m), 7.28 (2H, s), 7.22 (3H, m), 6.67 (1H, s), 6.48 (1H, s), 5.60 (1H, s), 2.72 (1H, s), 2.55 (3H, s), 2.27 (3H, s), 0.84 (2H, m), 0.79 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 168.6, 153.4, 152.6, 151.1, 144.1, 143.7, 139.2, 135.8, 134.9, 134.0, 132.9, 131.9, 129.7, 129.5, 128.0, 127.6, 123.3, 122.9, 121.8, 116.9, 114.2, 99.0, 89.5, 32.7, 24.7, 23.8, 9.8. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₇N₆O: 474.2168; found: 474.2176.

TBI-1231, 5-(4-Acetamidophenyl)-3-cyclohexylimino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.45 (1H, s), 7.91 (2H, d, J=8.1 Hz), 7.68 (2H, m), 7.28 (2H, m), 7.16 (3 m), 6.73 (1H, s), 6.54 (1H, m), 5.35 (1H, s), 3.08 (1 m), 2.56 (3H, s), 2.29 (3H, s), 1.44 (10H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 168.8, 153.4, 150.7, 143.8, 139.6, 135.0, 134.3, 131.5, 129.8, 129.1, 128.2, 123.4, 121.7, 114.5, 89.3, 57.3, 33.2, 25.7, 24.6, 23.8. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₂H₃₃N₆O: 516.2638: found: 516.2612.

TBI-1236, 5-(4-Methoxycarbonylphenyl)-3-(1-ethylethyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.39 (2H, d, J=8.1 Hz), 7.82 (2H, m), 7.68 (2H, d, J=6.9 Hz), 7.45 (2H, d, J=8.4 Hz), 7.12 (2H, m), 6.92 (2H, s), 6.39 (1H, d, J=7.8 Hz), 5.24 (1H, s), 4.02 (6H, s), 3.41 (1H, m), 1.07 (6H, d, J=6.3 Hz). ¹³C-NMR (100 MHz, CDCl₃) δ: 166.0, 155.5, 151.2, 150.5, 142.9, 141.7, 138.8, 135.6, 134.5, 132.6, 131.4, 131.3, 129.3, 128.2, 127.6, 124.9, 124.8, 122.9, 116.8, 113.7, 100.1, 89.3, 53.7, 52.6, 49.4, 23.5. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₈N₅O₃: 493.2114; found: 493.2113.

TBI-1237, 5-(4-Methoxycarbonylphenyl)-3-cyclopropylimino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.58 (1H, brs), 8.39 (2H, d, J=9.9 Hz), 7.82 (2H, d, J=7.8 Hz), 7.67 (1H, d, J=7.5 Hz), 7.47 (2H, d, J=6.9 Hz), 7.11 (2H, m), 6.90 (2H, m), 6.37 (1H, d, J=8.1 Hz), 5.50 (1H, s), 4.01 (6H, s), 2.68 (1H, m), 0.83 (4H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 166.0, 155.4, 152.4, 151.4, 142.6, 141.7, 138.9, 135.7, 134.3, 132.7, 131.4, 129.4, 128.2, 127.6, 125.0, 124.7, 122.9, 116.8, 113.7, 100.0, 89.7, 53.7, 52.6, 32.9, 10.8. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₆N₅O₃: 491.1957; found: 491.1960.

TBI-1426, 5-(3,4-Difluorophenyl)-3-cyclopropylimino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.58 (1H, s), 7.82 (2H, m), 7.66 (1H, d, J=8.1 Hz), 7.52 (1H, m), 7.12 (3H, m), 6.09 (1H, m), 6.86 (1H, s), 6.42 (1H, d, J=8.4 Hz), 5.54 (1H, s), 4.01 (3H, s), 2.77 (1H, m), 0.93 (2H, d, J=6.0 Hz, 0.86 (2H, d, J=2.7 Hz). ¹³C NMR (100 MHz, CDCl₃) 155.5, 153.1, 152.4, 151.5, 150.5, 149.6, 142.7, 139.0, 135.7, 133.7, 131.6, 128.2, 127.7, 125.1, 124.7, 123.1, 120.1, 118.9, 116.8, 113.5, 100.5, 89.6, 53.7, 33.0, 10.2. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₂F₂N₅O: 470.1787; found: 470.1762.

TBI-1427, 5-(3,4-Difluorophenyl)-3-(4-methoxycyclohexyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.94 (1H, brs), 7.82 (2H, m), 7.69 (1H, d, J=8.1 Hz), 7.53 (1H, m), 7.22 (1H, m), 7.15 (3H, m), 6.92 (2H, m), 6.46 (1H, d, J=7.95 Hz), 5.26 (1H, s), 4.03 (3H, s), 3.36 (3H, s), 3.27 (1H, m), 3.16 (1H, m), 2.05 (2H, m), 1.73 (2H, 1.40 (2H, 1.26 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 155.4, 153.2, 152.2, 151.1, 149.7, 142.7, 138.8, 135.6, 134.7, 133.5, 131.3, 128.4, 127.8, 125.7, 124.7, 123.1, 119.9, 118.7, 116.8, 113.6, 100.2, 89.2, 78.2, 56.9, 55.8, 33.7, 30.8, 29.3. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₁H₃₀F₂N₅O₂: 542.2362; found: 542.2338.

TBI-1428, 5-(3,4-Difluorophenyl)-3-(4-tetrahydropyranyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 9.08 (1H, s), 7.83 (2H, d, J=7.5 Hz), 7.71 (1H, d, J=6.6 Hz), 7.55 (1H, m), 7.18 (4H, m), 6.91 (2H, m), 6.46 (1H, d, J=7.8 Hz), 5.25 (1H, s), 4.04 (5H, brs), 3.49 (3H, m), 1.68 (4H, brs). ¹³C NMR (100 MHz, CDCl₃) δ: 155.3, 153.2, 152.2, 151.0, 149.8, 142.6, 138.8, 135.6, 134.9, 133.6, 131.2, 128.4, 127.9, 125.7, 124.8, 124.4, 123.3, 120.0, 118.7, 116.8, 113.7, 100.3, 88.9, 65.5, 53.8, 53.3, 33.3. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₅F₂N₅O₂: 514.2049; found: 514.2054.

TBI-1429, 5-(3,4-Difluorophenyl)-3-cyclopropylimino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.55 (1H, d, J=1.8 Hz), 8.33 (1H, d, J=4.2 Hz), 7.75 (1H, d, J=8.1 Hz), 7.66 (1H, d, J=6.3 Hz), 7.54 (1H, m), 7.30 (1H, m), 7.23 (1H, m), 7.15 (3H, m), 6.77 (1H, s), 6.43 (1H, d, J=7.8 Hz), 5.54 (1H, s), 2.78 (1H, m), 0.93 (2H, d, J=6.9 Hz), 0.84 (2H, hrs). ¹³C NMR (100 MHz, CDCl₃) 153.1, 152.1, 151.2, 150.6, 149.7, 144.5, 144.1, 143.5, 136.6, 135.6, 134.6, 133.6, 131.5, 128.3, 128.2, 127.8, 125.8, 123.6, 123.1, 120.0, 118.8, 113.6, 99.4, 89.5, 33.0, 10.1. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₆H₂₀F₂N₅: 440.1681; found: 440.1667.

TBI-1430, 5-(3,4-Difluorophenyl)-3-(4-methoxycyclohexyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.57 (1H, s), 8.34 (1H, (1H, J=4.5 Hz), 7.77 (1H, d, J=7.8 Hz), 7.69 (1H, d, J=7.2 Hz), 7.53 (1H, m), 7.31 (1H, m), 7.20 (1H, m), 7.16 (3H, m), 6.82 (1H, s), 6.48 (1H, d, J=8.1 Hz), 5.27 (1H, s), 3.37 (3H, s), 3.2 (1H, m), 3.13 (1H, m), 2.10 (2H, m), 1.71 (2H, m), 1.42 (2H, m), 1.21 (2H, m). ¹³C NMR (100 MHz, CDCl₃) 153.1, 152.2, 151.0, 150.8, 150.6, 149.7, 144.4, 144.0, 143.6, 136.6, 135.6, 134.7, 133.5, 131.2, 128.5, 127.9, 125.6, 123.6, 123.2, 119.9, 118.7, 113.7, 99.5, 89.1, 78.4, 57.4, 55.8, 31.2, 29.9. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₂₈F₂N₅O: 512.2256; found: 512.2245.

TBI-1431, 5-(3,4-Difluorophenyl)-3,5-dihydro-1′-(2-methoxy-3-pyridyl)-2′,2′-dimethyl-1′H-imidazo[4′,5′,2,3]phenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.24 (1H, d, J=4.5 Hz), 7.54 (3H, m), 7.22 (1H, m), 7.12 (2H, d, J=8.4 Hz), 7.02 (2H, m), 6.42 (1H, d, J=8.4 Hz), 5.48 (1H, s), 5.40 (1H, s), 3.93 (3H, s), 1.26 (6H, s). ¹³C NMR (100 MHz, CDCl₃) δ: 160.8, 159.1, 153.1, 152.2, 150.5, 149.7, 149.2, 147.1, 139.1, 138.3, 135.9, 133.7, 131.0, 127.8, 126.8, 125.7, 123.4, 120.3, 119.8, 118.7, 117.0, 113.7, 96.1, 92.1, 91.5, 53.7, 27.0. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₂F₂N₅O: 470.1787; found: 470.1817.

TBI-1432, 5-(3,4-Difluorophenyl)-3-(4-tetrahydropyranyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 8.61 (1H, s), 8.36 (1H, d, J=4.2 Hz), 7.78 (1H, d, J=8.1 Hz), 7.72 (1H, d, J=8.9 Hz), 7.50 (1H, m), 7.33 (1H, m), 7.25 (1H, m), 7.22 (3H, m), 6.86 (1H, s), 6.49 (1H, d, J=7.5 Hz), 5.28 (1H, s), 4.00 (2H, d, J=5.4 Hz), 3.45 (3H, m), 1.66 (4H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 155.1, 152.2, 150.9, 150.7, 149.7, 144.5, 144.0, 143.6, 136.6, 135.6, 134.9, 133.5, 131.1, 128.5, 128.1, 125.6, 123.7, 123.4, 119.9, 118.6, 113.7, 99.6, 88.8, 66.0, 54.3, 33.5, 33.3. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₈H₂₄F₂N₅O: 484.1943; found: 484.1962.

TBI-1433, 5-(3,4-Difluorophenyl)-3-(4-methoxycyclohexyl)imino-2-(pyrimidin-2-yl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) δ: 9.66 (1H, s), 8.54 (1H, d, J=5.1 Hz), 8.47 (1H, s), 7.75 (1H, m), 7.58 (2H, m), 7.15 (3H, m), 0.82 (1H, m), 6.45 (1H, d, J=6.0 Hz), 5.24 (1H, s), 3.34 (3H, s), 3.18 (1H, m), 3.11 (1H, m), 2.05 (2H, m), 1.65 (2H, m), 1.32 (2H, m), 1.20 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 159.3, 157.9, 153.1, 152.2, 151.7, 150.6, 149.7, 140.1, 135.6, 134.9, 133.4, 131.7, 131.3, 128.9, 128.4, 128.2, 125.7, 123.1, 119.9, 118.7, 113.6, 108.5, 89.0, 78.4, 57.4, 55.8, 31.1, 29.8. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₇F₂N₆O: 513.2209; found: 513.2242.

TBI-1436, 5-(3,4-Difluorophenyl)-3-(1-methylethyl)imino-2-(2-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃), δ: 8.38 (1H, d, J=3.6 Hz), 8.27 (1H, s), 7.75 (1H, d, J=6.9 Hz), 7.54 (2 m), 7.25 (1H, m), 7.17 (3H, brs), 6.99 (1H, d, J=7.5 Hz), 6.85 (1H, s), 6.43 (1H, d, J=7.2 Hz), 5.26 (1H, s), 3.48 (1H, m), 1.10 (6H, brs). ¹³C NMR (100 MHz, CDCl₃) δ: 154.1, 153.1, 151.7, 150.3, 148.2, 141.0, 137.1, 135.7, 134.8, 133.7, 131.5, 128.7, 127.9, 125.8, 123.0, 119.9, 118.8, 116.3, 113.5, 112.9, 105.4, 89.0, 49.4, 23.7. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₆H₂₂F₂N₆: 442.1838; found: 442.1865.

TBI-1437, 5-(3,4-Difluorophenyl)-3-(1-methylethyl)imino-2-(pyrimidin-2-yl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃), δ: 8.55 (2H, d, J=4.8 Hz), 8.47 (1H, s), 7.76 (1H, d, J=63 Hz), 7.53 (1H, m), 7.21 (1H, m), 7.17 (3H, m), 6.82 (1H, t=4.8 Hz), 6.43 (1H, d, J=7.8 Hz), 5.27 (1H, s), 3.48 (1H, m), 1.10 (6H, brs). ¹³C NMR (100 MHz, CDCl₃) δ: 159.3, 157.7, 151.8, 150.0, 140.2, 135.6, 134.9, 133.6, 131.8, 128.9, 128.3, 125.8, 123.0, 120.0, 118.7, 113.5, 108.4, 89.2, 44.5, 23.5. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₅H₂₁F₂N₆: 443.1790; found: 443.1750.

TBI-1438, 5-(3,4-Difluorophenyl)-3-(1-methylethyl)imino-2-(3-cyano-2-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃), δ: 10.36 (1H, s), 8.57 (2H, m), 7.80 (2H, d, J=6.3 Hz), 7.57 (1H, m), 7.40 (1H, s), 7.22 (3H, m), 6.85 (1H, s), 6.48 (1H, d, J=6.9 Hz), 5.30 (1H, s), 3.52 (1H, m), 1.21 (6H, brs). ¹³C NMR (100 MHz, CDCl₃) δ: 155.9, 153.1, 152.8, 152.1, 151.1, 150.7. 142.5, 141.2, 140.0, 135.9, 135.3, 133.4, 131.3, 129.0, 128.5, 125.6, 123.5, 122.1, 120.0, 118.6. 116.1, 114.5, 113.8, 108.6, 97.0, 88.6, 48.9, 29.7, 23.4. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₇H₂₁F₂N₆: 467.1790; found: 467.1786.

TBI-1444, 5-(3,4-Difluorophenyl)-3-(4-methoxycyclohexyl)imino-2-(5-nitro-2-pyridyl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, DMSO-d₆), δ: 9.76 (1H, brs), 9.23 (1H, s), 8.48 (1H, s), 8.33 (1H, d, J=9.3 Hz), 7.89 (2H, m), 7.78 (1H, J=6.3 Hz), 7.52 (1H, m), 7.32 (3H, m), 6.65 (1H, d, J=8.4 Hz), 5.22 (1H, s), 3.31 (3H, s), 3.14 (1H, m), 3.11 (1H, m), 1.96 (2H, m), 1.66 (2H, m), 1.40 (2H, m), 1.13 (2H, m). ¹³C NMR (100 MHz, DMSO-d₆) δ: 159.3, 158.5, 151.4, 145.6, 144.9, 141.5, 137.1, 135.1, 134.1, 133.0, 132.2, 128.6, 126.4, 123.6, 120.3, 119.6, 118.7, 114.6, 109.3, 88.4, 77.5, 55.1, 47.6, 30.1, 29.4. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₃₀H₂₇F₂N₆O₃: 557.2107; found: 557.2133.

TBI-1445, 5-(3,4-Difluorophenyl)-3-(4-methoxycyclohexyl)imino-2-(pyrazin-2-yl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃) 8.43 (1H, s), 8.29 (2H, s), 8.06 (1H, d, J=12.4 Hz), 7.78 (1H, d, J=9.0 Hz), 7.55 (1H, m), 7.24 (1H, 7.21 (3H, m), 6.48 (1H, d, J=9.9 Hz), 5.25 (1H, s), 3.37 (3H, s), 3.22 (1H, m), 3.12 (1H, m), 2.09 (2H, m), 1.71 (2H, m), 1.47 (2 m), 1.23 (2H, m). ¹³C NMR (100 MHz, CDCl₃) δ: 153.1, 151.3, 151.0, 150.9, 141.6, 139.9, 136.3, 135.7, 135.0, 133.4, 131.6, 129.0, 128.6, 125.6, 123.3, 120.0, 118.7, 113.7, 107.6, 88.9, 78.4, 57.3, 55.8, 31.2, 30.0, 29.8. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₉H₂₇F₂N₆O: 513.2209; found: 513.2178.

TBI-1446, 5-(3,4-Difluorophenyl)-3-(1-methylethyl)imino-2-(pyrazin-2-yl)amino-3,5-dihydrophenazine

¹H NMR (300 MHz, CDCl₃8.43 (1H, s), 8.29 (2H, d, J=9.9 Hz), 8.06 (1H, s), 7.77 (1H, d, J=5.7 Hz), 7.55 (1H, m), 7.26 (1H, m), 7.17 (3H, m), 6.45 (1H, d, J=8.4 Hz), 5.27 (1H, s), 3.49 (1H, m), 1.12 (6H, m). ¹³C NMR (100 MHz, CDCl₃) 153.2, 151.4, 151.0, 150.7, 150.3, 141.6, 140.0, 136.3, 135.6, 135.0, 133.5, 131.6, 129.0, 128.4, 125.7, 123.2, 120.0, 118.7, 113.6, 107.5, 88.9, 49.4, 23.7, 23.5. HRMS (ESI-TOF⁺): m/z [M+H]⁺ calcd for C₂₅H₂₁F₂N₆: 443.1790; found: 443.1776.

REFERENCES CITED

The content of each of the documents listed below is hereby incorporated by reference.

U.S. Patent Documents

U.S. Pat. No. 3,499,899

Non-Patent Publications

Barry, V. C., Belton, J. G., Conalty, M. L., Denneny, J. M., Edward, D. W., O'Sullivan, J. F., Twomey, D., Winder, F. A new series of phenazines (rimino-compounds) with high antituberculosis activity. Nature 179: 1013-1015 (1957).
Ma Z, Lienhardt C. Clin Chest Med. 30(4):755-68 (2009).
V. M. Reddy, G. Nadadhur, D. Daneluzzi, J. F. O'Sullivan, P. R. J. Gangadharam, Antimicrobial Agents and Chemother., 40, 633-636 (1996).

Claims

1. A compound having a structure of:

wherein

R1 is a substituent selected from the group consisting of H, alkyl, alkoxy, monoalkylamino, dialkylamino, heterocycloalkyl containing at least one nitrogen atom, halo, CF3, OCF3, SCH3, SOCH3, and combinations of any two or three thereof, wherein the two or three substituents are the same;

R2 is a substituent selected from the group consisting of alkyl, and cycloalkyl;

R3 is a substituent selected from the group consisting of H, alkyl, alkoxy, monoalkylamino, dialkyl amino, heterocycloalkyl containing at least one nitrogen atom, halo, NHCOCH3, and combinations of any two or three thereof, wherein the two or three substituents are the same or different;

R4 is a substituent selected from the group consisting of H, alkyl, alkoxy, halo, or monoalkylamino, dialkylamino, and heterocycloalkyl containing at least one nitrogen atom;

X is N;

Y is CH or N; and

Z is CH or N.

2. (canceled)

3. The compound of claim 1, wherein one or more of R1, R3, and R4 are heterocycloalkyl containing at least one nitrogen atom and wherein the heterocycloalkyl further comprises one or more additional heteroatoms selected from the group consisting of O, S or NR′, wherein R′ is an alkyl group.

4. (canceled)

5. The compound of claim 1, wherein R2 is cycloalkyl and wherein the cycloalkyl further comprises O, S, or NR′, wherein R′ is an alkyl group.

6. (canceled)

7. A pharmaceutical composition comprising a therapeutically effective amount of the compound of claim 1 and a pharmaceutically acceptable excipient, adjuvant, carrier, buffer or stabilizer.

8. (canceled)

9. The pharmaceutical composition of claim 7, further comprising one or more additional anti-infective treatments.

10. A method of preventing and treating microbial infection comprising administering the pharmaceutical composition of claim 7.

11. The method of claim 10, wherein the microbial infection is caused by Mycobacterium tuberculosis.

12-26. (canceled)