262295-90-9

Basic information

• Product Name: Benzonitrile, 4-[(2S,5R)-2,5-dimethyl-4-(phenylmethyl)-1-piperazinyl]-2-(trifluorometh yl)-
• CAS NO: 262295-90-9
• Molecular Formula: C21H22F3N3
• Molecular Weight: 373.421
• Mol File: 262295-90-9.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: Benzonitrile, 4-[(2S,5R)-2,5-dimethyl-4-(phenylmethyl)-1-piperazinyl]-2-(trifluorometh yl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzonitrile, 4-[(2S,5R)-2,5-dimethyl-4-(phenylmethyl)-1-piperazinyl]-2-(trifluorometh yl)-(262295-90-9)
• EPA Substance Registry System: Benzonitrile, 4-[(2S,5R)-2,5-dimethyl-4-(phenylmethyl)-1-piperazinyl]-2-(trifluorometh yl)-(262295-90-9)

Safety Data

• Hazardous Substances Data: 262295-90-9(Hazardous Substances Data)

Upstream product

• 262295-89-6 (3S,6R)-1-benzyl-3,6-dimethylpiperazine-2,5-dione 
• 216532-43-3 (-)-(2R,5S)-1-benzyl-2,5-dimethylpiperazine 
• 194853-86-6 4-fluoro-2-(trifluoromethyl)benzonitrile 

Downstream Products

• 262295-87-4 (+)-(2S,5R)-4-(2,5-dimethylpiperazin-1-yl)-2-(trifluoromethyl)benzonitrile 

Relevant articles and documents

(+)-(2R,5S)-4-[4-cyano-3-(trifluoromethyl)phenyl]-2,5-dimethyl-N-[6- (trifluoromethyl)pyridin-3-yl]piperazine-1-carboxamide (YM580) as an orally potent and peripherally selective nonsteroidal androgen receptor antagonist

A novel series of trans-N-aryl-2,5-dimethylpiperazine-1-carboxamide derivatives was synthesized and their androgen receptor (AR) antagonist activities and in vivo antiandrogenic effects were evaluated. Pharmacological assays indicated that compound 33 was a potent AR antagonist, and subsequent optical resolution provided (+)-(2R,5S)4-[4-cyano-3-(trifluoromethyl)phenyl]-2, 5-dimethyl-N-[6(triflouromethyl)pyridin-3-yl]piperazine-1-carboxamide (33a, YM580) which exhibited the most potent antiandrogenic activity. Unlike bicalutamide, compound 33a decreased the weight of rat ventral prostate in a dose-dependent manner (ED50 = 2.2 mg/kg/day), and induced the maximum antiandrogenic effect, comparable to that of surgical castration, without significantly affecting serum testosterone levels. Compound 33a is a promising clinical candidate for prostate cancer monotherapy.