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 journal › Article

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
Externally publishedYes

Fingerprint

Androgen Antagonists
Pyrroles
Androgen Receptors
Scaffolds
Androgens
Cytoplasmic and Nuclear Receptors
Ligands
Androgen Receptor Antagonists
Flutamide
Bearings (structural)
Structure-Activity Relationship
Lead compounds
Carcinoma
Cells
Growth
Derivatives

Keywords

  • Androgen
  • Antagonist
  • Pyrrole-2-carboxamides

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science

Cite this

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

Wakabayashi, KI, Miyachi, H, Hashimoto, Y & Tanatani, A 2005, 'Novel non-steroidal/non-anilide type androgen antagonists: Discovery of 4-substituted pyrrole-2-carboxamides as a new scaffold for androgen receptor ligands', Bioorganic and Medicinal Chemistry, vol. 13, no. 8, pp. 2837-2846. https://doi.org/10.1016/j.bmc.2005.02.019
Wakabayashi KI, Miyachi H, Hashimoto Y, Tanatani A. Novel non-steroidal/non-anilide type androgen antagonists: Discovery of 4-substituted pyrrole-2-carboxamides as a new scaffold for androgen receptor ligands. Bioorganic and Medicinal Chemistry. 2005 Apr 15;13(8):2837-2846. https://doi.org/10.1016/j.bmc.2005.02.019
Wakabayashi, Ken Ichi ; Miyachi, Hiroyuki ; Hashimoto, Yuichi ; Tanatani, Aya. / Novel non-steroidal/non-anilide type androgen antagonists : Discovery of 4-substituted pyrrole-2-carboxamides as a new scaffold for androgen receptor ligands. In: Bioorganic and Medicinal Chemistry. 2005 ; Vol. 13, No. 8. pp. 2837-2846.
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