Publication number: 20050272667
Abstract: The present invention provides analog and derivative compounds of (S,S,R)-(?)-actinonin and methods of asymmetric synthesis thereof having a structure: where R1 is hydrogen, C(O)R6 or R1 in combination with N is 2-oxomorpholine, R2 is hydrogen, methyl, CH2CH(CH3)2, (CH2)2CH3, CH(CH3)2, (CH2)3CH3, (CH2)4NH2, (CH2)3CO2H, phenyl, 3,4-dichlorophenyl, biphenyl, benzyl, 4-hydroxybenzyl, piperidine, N-Boc-4-piperidine, CH2-(N-Boc-4-piperidine), 4-tetrahydropyran, CH2-4-tetrahydropyran, 3-methyl indolyl, 2-naphthyl, 3-pyridyl, 4-pyridyl, 3-thienyl, R3 is R2 or C3-8alkyl, R4 is C1-3alkyl, R5 is NH2, OH, NHOH, NHOCH3, N(CH3)OH, N(CH3)OCH3, NHCH2CH3, NH(CH2CH3), NHCH2(2,4-(OCH3)2Ph, NHCH2(4-NO2)Ph, NHN(CH3)2, proline, or 2-hydroxymethyl pyrrolidine and R6 is an optionally substituted or halogenated alkyl, aryl, heteroalkyl or heteroaryl amine where R6 further comprising a cyclic or bicyclic structure.
Type:
Application
Filed:
May 2, 2005
Publication date:
December 8, 2005
Inventors:
David Scheinberg, William Bornmann, Francis Sirotnak, Howard Scher, Ephraim Vidal, Christopher Borella
Patent number: 6887887
Abstract: The present invention provides methods for the asymmetric synthesis of (S,S,R)-(?)-actinonin and its analogs and the compounds thereby synthesized having a structural formula: where R1 is an optionally substituted or halogenated alkyl, aryl, heteroalkyl or heteroaryl amine, said R1 further comprising a cyclic or bicyclic structure; R2 is methyl, CH2CH3, (CH2)2CH3, C(CH3)3, phenyl, 3,4-dichlorophenyl, biphenyl, benzyl, 4-hydroxybenzyl, piperidine, N-Boc-4-piperidine, CH2-(N-Boc-4-piperidine), 4-tetrahydropyran, CH2-4-tetrahydropyran, 3-methyl indolyl, 2-naphthyl, 3-pyridyl, 4-pyridyl, 3-thienyl; R3 is R2 or C3-8alkyl, R4 is C1-3alkyl; and R5 is NH2, OH, NHOH, NHOCH3, N(CH3)OH, N(CH3)OCH3, NHCH2CH3, NH(CH2CH3), NHCH2(2,4-(OCH3)2Ph, NHCH2(4-NO2)Ph, NHN(CH3)2, proline, or 2-hydroxymethyl pyrrolidine.
Type:
Grant
Filed:
June 25, 2003
Date of Patent:
May 3, 2005
Assignee:
Sloan-Kettering Institute for Cancer Research
Inventors:
William G. Bornmann, Francis Sirotnak, Howard Scher, Ephraim Vidal, Christopher Borella, David Scheinberg
Patent number: 6660741
Abstract: The present invention provides methods for the asymmetric synthesis of (S,S,R)-(−)-actinonin and its analogs and the compounds thereby synthesized having a structural formula:
where R1 is an optionally substituted or halogenated alkyl, aryl, heteroalkyl or heteroaryl amine, said R1 further comprising a cyclic or bicyclic structure; R2 is methyl, CH2CH3, (CH2)2CH3, C(CH3)3, phenyl, 3,4-dichiorophenyl, biphenyl, benzyl, 4-hydroxybenzyl, piperidine, N-Boc-4-piperidine, CH2-(N-Boc-4-piperidine), 4-tetrahydropyran, CH2-4-tetrahydropyran, 3-methyl indolyl, 2-naphthyl, 3-pyridyl, 4-pyridyl, 3-thienyl; R3 is R2 or C3-8alkyl, R4 is C1-3alkyl; and R5 is NH2, OH, NHOH, NHOCH3, N(CH3)OH, N(CH3)OCH3, NHCH2CH3, NH(CH2CH3), NHCH2(2,4-(OCH3)2Ph, NHCH2(4-NO2)Ph, NHN(CH3)2, proline, or 2-hydroxymethyl pyrrolidine.
Type:
Grant
Filed:
March 19, 2002
Date of Patent:
December 9, 2003
Assignee:
Sloan-Kettering Institute for Cancer Research
Inventors:
William G. Bornmann, Francis Sirotnak, Howard Scher, Ephraim Vidal, Christopher Borella, David Scheinberg
