INHIBITORS OF STEROID-BIOSYNTHESIS - PREPARATION OF 5,10-SECOESTR-4-YNES
INHIBITORS OF STEROID-BIOSYNTHESIS - PREPARATION OF 5,10-SECOESTR-4-YNES
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DOI：
10.1021/jo00148a017
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发表时间：
1982-01-01
影响因子：
3.6
通讯作者：
PARIKH, VD
中科院分区：
文献类型：
--
作者：
COVEY, DF;PARIKH, VD
报道了5，10-雌酮-4-炔-3，10，17-三酮的两个新的合成方法，5，10-雌酮-4-炔-3，10，17-三酮是一种对细菌和哺乳动物都具有不可逆抑制作用的5，10-雌酮-3，10，17-三酮。一条合成路线提供了3，β-羟基-4-乙酰基-5，10-秒类固醇，另一条路线提供了3，α-羟基-4-乙酰基5，10-秒类固醇。由于它们作为相应的3α和3β-羟基类固醇脱氢酶的基于机理的抑制剂的潜在用途，开发了通向这些表位α，β-乙酰醇的立体专一性路线。
Two novel syntheses of 5,10-secoestr-4-yne-3,10,17-trione, a powerful irreversible inhibitor of both bacterial and mammalian .DELTA.5-3-keto steroid isomerases, are described. One synthetic route makes available 3.beta.-hydroxy-4-acetylenic 5,10-seco steroids and the other provides 3.alpha.-hydroxy-4-acetylenic 5,10-seco steroids. Stereospecific routes to these epimeric .alpha.,.beta.-acetylenic alcohols were developed because of their potential utility as mechanism-based inhibitors of the corresponding 3.alpha.- and 3.beta.-hydroxy steroid dehydrogenases.