Novel non-steroidal/non-anilide type androgen antagonists: Discovery of 4-substituted pyrrole-2-carboxamides as a new scaffold for androgen receptor ligands

Ken Ichi Wakabayashi; Hiroyuki Miyachi; Yuichi Hashimoto; Aya Tanatani

doi:10.1016/j.bmc.2005.02.019

Novel non-steroidal/non-anilide type androgen antagonists: Discovery of 4-substituted pyrrole-2-carboxamides as a new scaffold for androgen receptor ligands

Ken Ichi Wakabayashi, Hiroyuki Miyachi, Yuichi Hashimoto, Aya Tanatani

Faculty of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

23 Citations (Scopus)

Abstract

We designed and synthesized novel pyrrole-2-carboxamide derivatives as androgen antagonists. Compounds 10 and 13 bearing benzylamine or aniline at the 4-position of the pyrrole ring showed moderate androgen antagonistic activity, and inhibited the androgen-dependent growth of Shionogi carcinoma cells (SC-3). Study of the structure-activity relationships of compound 13 led to a potent androgen antagonist 36, which has higher affinity than flutamide (4) for androgen nuclear receptor (AR). Thus, pyrrole-2-carboxamide is a new scaffold for developing AR antagonists.

Original language	English
Pages (from-to)	2837-2846
Number of pages	10
Journal	Bioorganic and Medicinal Chemistry
Volume	13
Issue number	8
DOIs	https://doi.org/10.1016/j.bmc.2005.02.019
Publication status	Published - Apr 15 2005

Keywords

Androgen
Antagonist
Pyrrole-2-carboxamides

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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Novel non-steroidal/non-anilide type androgen antagonists : Discovery of 4-substituted pyrrole-2-carboxamides as a new scaffold for androgen receptor ligands. / Wakabayashi, Ken Ichi; Miyachi, Hiroyuki; Hashimoto, Yuichi; Tanatani, Aya.

In: Bioorganic and Medicinal Chemistry, Vol. 13, No. 8, 15.04.2005, p. 2837-2846.

Research output: Contribution to journal › Article › peer-review

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abstract = "We designed and synthesized novel pyrrole-2-carboxamide derivatives as androgen antagonists. Compounds 10 and 13 bearing benzylamine or aniline at the 4-position of the pyrrole ring showed moderate androgen antagonistic activity, and inhibited the androgen-dependent growth of Shionogi carcinoma cells (SC-3). Study of the structure-activity relationships of compound 13 led to a potent androgen antagonist 36, which has higher affinity than flutamide (4) for androgen nuclear receptor (AR). Thus, pyrrole-2-carboxamide is a new scaffold for developing AR antagonists.",

keywords = "Androgen, Antagonist, Pyrrole-2-carboxamides",

author = "Wakabayashi, {Ken Ichi} and Hiroyuki Miyachi and Yuichi Hashimoto and Aya Tanatani",

note = "Funding Information: This work was supported in part by the Mochida Memorial Foundation, the Uehara Memorial Foundation for Medical and Pharmaceutical Research, and Grants-in-Aid for Scientific Research from The Ministry of Education, Culture, Sports, Science and Technology, Japan, and the Japan Society for the Promotion of Science.",

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AU - Wakabayashi, Ken Ichi

AU - Miyachi, Hiroyuki

AU - Hashimoto, Yuichi

AU - Tanatani, Aya

N1 - Funding Information: This work was supported in part by the Mochida Memorial Foundation, the Uehara Memorial Foundation for Medical and Pharmaceutical Research, and Grants-in-Aid for Scientific Research from The Ministry of Education, Culture, Sports, Science and Technology, Japan, and the Japan Society for the Promotion of Science.

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N2 - We designed and synthesized novel pyrrole-2-carboxamide derivatives as androgen antagonists. Compounds 10 and 13 bearing benzylamine or aniline at the 4-position of the pyrrole ring showed moderate androgen antagonistic activity, and inhibited the androgen-dependent growth of Shionogi carcinoma cells (SC-3). Study of the structure-activity relationships of compound 13 led to a potent androgen antagonist 36, which has higher affinity than flutamide (4) for androgen nuclear receptor (AR). Thus, pyrrole-2-carboxamide is a new scaffold for developing AR antagonists.

AB - We designed and synthesized novel pyrrole-2-carboxamide derivatives as androgen antagonists. Compounds 10 and 13 bearing benzylamine or aniline at the 4-position of the pyrrole ring showed moderate androgen antagonistic activity, and inhibited the androgen-dependent growth of Shionogi carcinoma cells (SC-3). Study of the structure-activity relationships of compound 13 led to a potent androgen antagonist 36, which has higher affinity than flutamide (4) for androgen nuclear receptor (AR). Thus, pyrrole-2-carboxamide is a new scaffold for developing AR antagonists.

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Novel non-steroidal/non-anilide type androgen antagonists: Discovery of 4-substituted pyrrole-2-carboxamides as a new scaffold for androgen receptor ligands

Abstract

Keywords

ASJC Scopus subject areas

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