Discovery and structure-activity relationships of new steroidal compounds bearing a carboxy-terminal side chain as androgen receptor pure antagonists.

Discovery and structure-activity relationships of new steroidal compounds bearing a carboxy-terminal side chain as androgen receptor pure antagonists. Research Abstract Details 

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Discovery and structure-activity relationships of new steroidal compounds bearing a carboxy-terminal side chain as androgen receptor pure antagonists. Abstract Text:

Kazutaka Tachibana,Ikuhiro Imaoka,Hitoshi Yoshino,Nobuaki Kato,Mitsuaki Nakamura,Masateru Ohta,Hiromitsu Kawata,Kenji Taniguchi,Nobuyuki Ishikura,Masahiro Nagamuta,Etsuro Onuma,Haruhiko Sato,Kazutaka Tachibana,Ikuhiro Imaoka,Hitoshi Yoshino,Nobuaki Kato,Mitsuaki Nakamura,Masateru Ohta,Hiromitsu Kawata,Kenji Taniguchi,Nobuyuki Ishikura,Masahiro Nagamuta,Etsuro Onuma,Haruhiko Sato,

Lead optimization of CH4892280 (4), an androgen receptor (AR) pure antagonist, was investigated. Compounds 6 and 7, which have a carboxylic acid at the end of the side chain at the position 7alpha of dihydrotestosterone (DHT), showed partial agonistic activities in reporter gene assay (RGA). Conversion of the steroidal core structure to 17alpha-methyltestosterone gave compound 14, which showed weak pure antagonistic activity. Optimization of the side chain by the insertion of a phenyl ring led to compounds 22 and 28-30, which showed pure antagonistic activities at submicromolar concentrations. The structure-activity relationships were clarified.

Discovery and structure-activity relationships of new steroidal compounds bearing a carboxy-terminal side chain as androgen receptor pure antagonists. Publishing Authors By Initials

K Tachibana,I Imaoka,H Yoshino,N Kato,M Nakamura,M Ohta,H Kawata,K Taniguchi,N Ishikura,M Nagamuta,E Onuma,H Sato,K Tachibana,I Imaoka,H Yoshino,N Kato,M Nakamura,M Ohta,H Kawata,K Taniguchi,N Ishikura,M Nagamuta,E Onuma,H Sato,

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Discovery and structure-activity relationships of new steroidal compounds bearing a carboxy-terminal side chain as androgen receptor pure antagonists. Journal Published:

PUBLICATION TYPE: Journal Article

Journal: Bioorganic & medicinal chemistry letters

VOLUME: 17

Page Numbers: 5573-6

Journal Abbreviation: Bioorg. Med. Chem. Lett.

ISSN: 0960-894X

DAY: 22

MONTH: 08

YEAR: 2007

Discovery and structure-activity relationships of new steroidal compounds bearing a carboxy-terminal side chain as androgen receptor pure antagonists. Information

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LANGUAGE: eng

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Grant and Affiliation Information for Discovery and structure-activity relationships of new steroidal compounds bearing a carboxy-terminal side chain as androgen receptor pure antagonists.

AFFILIATION: Fuji Gotemba Research Laboratories, Chugai Pharmaceutical Co. Ltd., 1-135 Komakado, Gotemba, Shizuoka 412-8513, Japan. tachibanakzt@chugai-pharm.co.jp

Country: England

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MEDLINETA: Bioorg Med Chem Lett

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