Inhibition of steroid 5. alpha.-reductase by unsaturated 3-carboxy steroids

…, MA Levy, HJ Oh, JM Erb, JI Heaslip…

Index: Holt, Dennis A.; Levy, Mark A.; Oh, Hye-Ja; Erb, Jill M.; Heaslip, Julie I.; et al. Journal of Medicinal Chemistry, 1990 , vol. 33, # 3 p. 943 - 950

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Citation Number: 132

Abstract

A series of unsaturated steroids bearing a 3-carboxy substituent has been prepared and assayed in vitro as inhibitors of human and rat prostatic steroid Sa-reductase (EC 1.3. 1.30). It is proposed that the observed tight binding of the 3-androstene-3-carboxylic acids is due to mimicry of a putative, high-energy, enzymebound enolate intermediate formed during the NADPH-dependent conjugate reduction of testosterone by steroid 5a-reductase. These ...