Patent number: 8927570
Abstract: Provided are 1-aryl or 1-heteroaryl substituted beta-carboline compounds or indole analogs thereof having the structure: where X is NH, N—C1-C4 alkyl, S, or O; R1 is 1-naphthyl or 1-dihydroacenaphthenyl, each optionally substituted with a halogen; and R2, R3, R4, R5, R6, and R7 are independently H H, OH, halogen, CN, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, —C(O)OC1-C4 ester, —C1-C4—SO2—NH—C1-C4 sulfonamide, or phenyl with the proviso that X is NH, R1 is 1-naphthyl or 1-naphthyl substituted with a halogen and one of R5, R6, or R7 is C1-C4 alkoxy, then R2, R3, R4, R5, R6, and R7 are independently H, OH, halogen, CN, C1-C4 haloalkoxy, —C(O)OC1-C4 ester, —C1-C4—SO2—NH—C1-C4 sulfonamide, or phenyl such that at least two of R2, R3, R4, R5, R6, and R7 are other than H. Also provided are methods for inhibiting proliferation of cells associated with a cell proliferative disease by contacting the cell with the compounds provided herein.
Type:
Grant
Filed:
October 30, 2012
Date of Patent:
January 6, 2015
Inventor:
John K. Buolamwini
Publication number: 20130131070
Abstract: Provided are 1-aryl or 1-heteroaryl substituted beta-carboline compounds or indole analogs thereof having the structure: where X is NH, N—C1-C4 alkyl, S, or O; R1 is 1-naphthyl or 1-dihydroacenaphthenyl, each optionally substituted with a halogen; and R2, R3, R4, R5, R6, and R7 are independently H H, OH, halogen, CN, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, —C(O)OC1-C4 ester, —C1-C4—SO2—NH—C1-C4 sulfonamide, or phenyl with the proviso that X is NH, R1 is 1-naphthyl or 1-naphthyl substituted with a halogen and one of R5, R6, or R7 is C1-C4 alkoxy, then R2, R3, R4, R5, R6, and R7 are independently H, OH, halogen, CN, C1-C4 haloalkoxy, —C(O)OC1-C4 ester, —C1-C4—SO2—NH—C1-C4 sulfonamide, or phenyl such that at least two of R2, R3, R4, R5, R6, and R7 are other than H. Also provided are methods for inhibiting proliferation of cells associated with a cell proliferative disease by contacting the cell with the compounds provided herein.
Type:
Application
Filed:
October 30, 2012
Publication date:
May 23, 2013
Inventor:
John K. Buolamwini
Patent number: 5236902
Abstract: The present invention is directed to compounds capable of binding to the es nucleoside transporter of animal cells having the general formula: ##STR1## wherein n is 1-12; E is H, halogen, NH.sub.2, OH, OCH.sub.3, O(CH.sub.2).sub.n CH.sub.3 (where n is 1 to 12), SH, SR (where R is CH.sub.3 or (CH.sub.2).sub.n CH.sub.3 and n is 1 to 12); A is HN, S, O, Se; X is N or C; Y is N or C; Z is N or C; R.sub.1 is H or acyl; R.sub.2 is C1 to C20 substituted or unsubstituted alkyl or heteroalkyl; substituted or unsubstituted aliphatic carbocycle or heterocycle; substituted or unsubstituted arene or heteroarene, aryl or substituted aryl; heteroaryl or substituted heteroaryl; R.sub.3 is H, halogen, NO.sub.2, N.sub.3, SH, SR (where R is CH.sub.3 or (CH.sub.2).sub.n CH.sub.3 and n is 1 to 12); R.sub.4 is H, OH is halogen; R.sub.5 is H, OH, halogen, N.sub.3, acetal, hemiacetal and R.sub.6 is H, --C.dbd.O--HN.sub.2 or --C.dbd.N when X is C and R.sub.6 is H when X is N.
Type:
Grant
Filed:
November 26, 1990
Date of Patent:
August 17, 1993
Assignee:
The Governors of the University of Alberta
Inventors:
Alan R. P. Paterson, Carol E. Cass, Wendy P. Gati, John K. Buolamwini, Gary P. Jamieson, David P. McAdam, William A. Sawyer, James S. Wiley, James D. Craik, Morris J. Robins
Patent number: RE35904
Abstract: The present invention is directed to compounds capable of binding to the es nucleoside transporter of animal cells having the general formula: ##STR1## wherein n is 1-12; E is H, halogen, NH.sub.2, OH, OCH.sub.3, O(CH.sub.2).sub.n CH.sub.3 (where n is 1 to 12), SH, SR (where R is CH.sub.3 or (CH.sub.2).sub.n CH.sub.3 and n is 1 to 12); A is HN, S, O, Se; X is N or C; Y is N or C; Z is N or C; R.sub.1 is H or acyl; R.sub.2 is C1 to C20 substituted or unsubstituted alkyl or heteroalkyl; substituted or unsubstituted aliphatic carbocycle or heterocycle; substituted or unsubstituted arene or heteroarene, aryl or substituted aryl; heteroaryl or substituted heteroaryl; R.sub.3 is H, halogen, NO.sub.2, N.sub.3, SH, SR (where R is CH.sub.3 or (CH.sub.2).sub.n CH.sub.3 and n is 1 to 12) .Iadd.when Y is C and R.sub.3 is absent when Y is N.Iaddend.; R.sub.4 is H, OH .?.is.!. .Iadd.or .Iaddend.halogen; R.sub.5 is H, OH, halogen, N.sub.3, acetal, hemiacetal.Iadd.; .Iaddend.and R.sub.6 is H, .?.--C.dbd.O--HN.sub.2 .!. .
Type:
Grant
Filed:
August 17, 1995
Date of Patent:
September 22, 1998
Assignee:
Governors of the University of Alberta
Inventors:
Alan R. P. Paterson, Carol E. Cass, Wendy P. Gati, John K. Buolamwini, Gary P. Jamieson, David P. McAdam, William A. Sawyer, James S. Wiley, James D. Craik, Morris J. Robins