Time-dependent inactivation of steroid C-17(20)lyase by 17 beta-cyclopropyl ether-substituted steroids

被引：17

作者：

Angelastro, MR

Marquart, AL

Weintraub, PM

Gates, CA

Laughlin, ME

Blohm, TR

Peet, NP

机构：

[1] Marion Merrell Dow Res. Institute, Cincinnati, OH 45215

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1996年 / 6卷 / 01期

关键词：

D O I：

10.1016/0960-894X(95)00566-C

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Androstenes bearing a cyclopropyl group attached to the C-17 beta position with a heteroatom linker, designed as mechanism-based inhibitors of steroid C-17(20) lyase, were found to be potent, time-dependent inhibitors of this enzyme.

引用

页码：97 / 100

页数：4

共 15 条

[1] 17-BETA-(CYCLOPROPYLAMINO)-ANDROST-5-EN-3-BETA-OL, A SELECTIVE MECHANISM-BASED INHIBITOR OF CYTOCHROME P45017-ALPHA (STEROID 17-ALPHA HYDROXYLASE-C17-20 LYASE) [J].

ANGELASTRO, MR ;

LAUGHLIN, ME ;

SCHATZMAN, GL ;

BEY, P ;

BLOHM, TR .

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1989, 162 (03) :1571-1577

[2] SYNTHESIS OF 2,19-BRIDGED ANDROSTENEDIONES [J].

BURKHART, JP ;

HUBER, EW ;

LASKOVICS, FM ;

PEET, NP .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (19) :5150-5154

[3] THE MECHANISM OF CYTOCHROME-P-450 DEPENDENT C-C BOND-CLEAVAGE - STUDIES ON 17-ALPHA-HYDROXYLASE-17,20-LYASE [J].

CORINA, DL ;

MILLER, SL ;

WRIGHT, JN ;

AKHTAR, M .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (11) :782-783

[4] MECHANISM-BASED INACTIVATION OF CYTOCHROME-P-450 BY HETEROATOM-SUBSTITUTED CYCLOPROPANES AND FORMATION OF RING-OPENED PRODUCTS [J].

GUENGERICH, FP ;

WILLARD, RJ ;

SHEA, JP ;

RICHARDS, LE ;

MACDONALD, TL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (21) :6446-6447

[5] CYTOCHROME-P-450 C-21SCC - ONE ENZYME WITH 2 ACTIONS - HYDROXYLASE AND LYASE [J].

HALL, PF .

JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY, 1991, 40 (4-6) :527-532

[6] SUICIDAL INACTIVATION OF CYTOCHROME-P-450 BY CYCLOPROPYLAMINES - EVIDENCE FOR CATION-RADICAL INTERMEDIATES [J].

HANZLIK, RP ;

TULLMAN, RH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (07) :2048-2050

[7]

JOHNSTON JO, 1993, J STEROID BIOCHEM, V44, P623

[8] KINETIC APPLICATIONS OF ELECTRON-PARAMAGNETIC RESONANCE SPECTROSCOPY .35. SEARCH FOR A DIALKYLAMINYL REARRANGEMENT - RING-OPENING OF N-CYCLOBUTYL-N-NORMAL-PROPYLAMINYL [J].

MAEDA, Y ;

INGOLD, KU .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (01) :328-331

[9]

NAKAJIN S, 1981, J BIOL CHEM, V256, P3871

[10] ELECTRON-SPIN-RESONANCE STUDIES ON THE RADICAL CATION MECHANISM OF THE RING-OPENING OF CYCLOPROPYLAMINES [J].

QIN, XZ ;

WILLIAMS, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (02) :595-597

← 1 2 →