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脱氢表雄酮硫酸酯和16α-卤代甾体的合成。

Synthesis of dehydroepiandrosterone sulfatide and 16 alpha-halogenated steroids.

作者信息

Abou-Gharbia M, Pashko L, Schwartz A, Swern D

出版信息

J Pharm Sci. 1981 Oct;70(10):1154-7. doi: 10.1002/jps.2600701017.

DOI:10.1002/jps.2600701017
PMID:6457907
Abstract

Dehydroepiandrosterone sulfatide was prepared in a 68% yield by the reaction of 5-androstene-3 beta-ol-17-one 3 sulfate (silver salt) with dipalmitoyl alpha-iodopropylene glycol. The sulfatide was found to be a more potent inhibitor of human glucose-6-phosphate dehydrogenase than dehydroepiandrosterone. 16 alpha-Halogenated steroids also were prepared by direct halogenation of the steroid or indirect halogenation of an appropriate steroidal intermediate. Among various halogenated steroids, 16 alpha-bromoepiandrosterone was 50 times as potent as dehydroepiandrosterone as an inhibitor of glucose-6-phosphate dehydrogenase.

摘要

通过5-雄烯-3β-醇-17-酮3-硫酸盐(银盐)与二棕榈酰α-碘代丙二醇反应,以68%的产率制备了硫酸脱氢表雄酮。发现该硫苷比脱氢表雄酮是更有效的人葡萄糖-6-磷酸脱氢酶抑制剂。16α-卤代甾体也通过甾体的直接卤化或合适甾体中间体的间接卤化来制备。在各种卤代甾体中,16α-溴表雄酮作为葡萄糖-6-磷酸脱氢酶抑制剂的效力是脱氢表雄酮的50倍。

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