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4-(Anilino)pyrrole-2-carboxamides: Novel non-steroidal/non-anilide type androgen antagonists effective upon human prostate tumor LNCaP cells with mutated nuclear androgen receptor.

Abstract：

:Various 4-(anilino)pyrrole-2-carboxamides were designed and synthesized as novel androgen receptor (AR) antagonists without steroidal or anilide structure, based on our strategy for developing full antagonists of nuclear receptors. Introduction of a bulky N-alkyl group, such as a cyclohexylmethyl or benzyl group, increased the binding affinity for wild-type AR and the potency for growth inhibition of androgen-dependent SC-3 cells. Among the compounds obtained, N-[4-[(benzyl)(4-nitrophenyl)amino]-1-methylpyrrole-2-carbonyl]pyrrolidine (22) is as potent an AR antagonist as the typical anilide-type AR antagonists hydroxyflutamide and bicalutamide. Further, compound 22 had potent binding affinity for T877A mutated AR, and dose-dependently inhibited the testosterone-induced production of prostate-specific antigen in LNCaP cells bearing T877A AR.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Wakabayashi K,Imai K,Miyachi H,Hashimoto Y,Tanatani A

doi

10.1016/j.bmc.2008.05.063

subject

Has Abstract

pub_date

2008-07-15 00:00:00

pages

6799-812

issue

14

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(08)00505-1

journal_volume

16

pub_type

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