N-Arylpiperazine-1-carboxamide Derivatives

N-Arylpiperazine-1-carboxamide Derivatives

A novel series of N-arylpiperazine-1-carboxamide derivatives was synthesized and their androgen receptor (AR) antagonist activities and in vivo antiandrogenic properties were evaluated. Reporter assays indicated that trans-2,5-dimethylpiperazine derivatives are potent AR antagonists, and in this ser...

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Veröffentlicht in:Chemical & pharmaceutical bulletin 2005-04, Vol.53 (4), p.402
Hauptverfasser: Kinoyama, Isao, Taniguchi, Nobuaki, Kawaminami, Eiji, Nozawa, Eisuke, Koutoku, Hiroshi, Furutani, Takashi, Kudoh, Masafumi, Okada, Minoru
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container_issue 4
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container_title Chemical & pharmaceutical bulletin
container_volume 53
creator Kinoyama, Isao
Taniguchi, Nobuaki
Kawaminami, Eiji
Nozawa, Eisuke
Koutoku, Hiroshi
Furutani, Takashi
Kudoh, Masafumi
Okada, Minoru
description A novel series of N-arylpiperazine-1-carboxamide derivatives was synthesized and their androgen receptor (AR) antagonist activities and in vivo antiandrogenic properties were evaluated. Reporter assays indicated that trans-2,5-dimethylpiperazine derivatives are potent AR antagonists, and in this series trans-N-4-[4-cyano-3-(trifluoromethyl)phenyl]-N-(2,4-difluorophenyl)-2,5-dimethylpiperazine-1-carboxamide (18g, YM-175735) exhibited the most potent antiandrogenic activity. Compared to bicalutamide, YM-175735 is an approximately 4-fold stronger AR antagonist and has slightly increased antiandrogenic activity, suggesting that YM-175735 may be useful in the treatment of prostate cancer.
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