TY - JOUR
T1 - Novel non-steroidal/non-anilide type androgen antagonists
T2 - Discovery of 4-substituted pyrrole-2-carboxamides as a new scaffold for androgen receptor ligands
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.
PY - 2005/4/15
Y1 - 2005/4/15
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.
KW - Androgen
KW - Antagonist
KW - Pyrrole-2-carboxamides
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U2 - 10.1016/j.bmc.2005.02.019
DO - 10.1016/j.bmc.2005.02.019
M3 - Article
C2 - 15781394
AN - SCOPUS:15244342943
VL - 13
SP - 2837
EP - 2846
JO - Bioorganic and Medicinal Chemistry
JF - Bioorganic and Medicinal Chemistry
SN - 0968-0896
IS - 8
ER -