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

Research output: Contribution to journalArticle

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 languageEnglish
Pages (from-to)2837-2846
Number of pages10
JournalBioorganic and Medicinal Chemistry
Volume13
Issue number8
DOIs
Publication statusPublished - Apr 15 2005

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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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