抗生育药物的研究——第四十一部分：开环甾族化合物——X：（±）2,6β -二乙基-7α -乙炔基-3-（对羟基苯基）-反式双环[4.3.0]壬烷-7β -醇各种立体异构体的合成
Studies in antifertility agents--Part XLI : Secosteroids--X : Syntheses of various stereoisomers of (+/-) 2,6 beta -diethyl-7 alpha -ethynyl-3-(p-hydroxyphenyl)-trans-bicyclo[4.3.0]nonan-7 beta-ol.
作者信息
Thingran A G, Gupta R C, Ray S, Agarwal A K, Singh M M, Anand N
出版信息
Steroids. 1983 Dec;42(6):627-34. doi: 10.1016/0039-128x(83)90126-5.
The syntheses of (+/-) 2 alpha,6 beta -diethyl-7 alpha -ethynyl-3 alpha-(p-hydroxyphenyl)-trans- bicyclo[4.3.0]nonan-7 beta-ol (8), (+/-)2 beta,6 beta-diethyl-7 alpha-ethynyl-3 beta-(p-methoxy-phenyl)-trans-bicyclo[4.3.0]nonan-7 beta-ol 12 and (+/-) 2 alpha,6 beta-diethyl-7 alpha-ethynyl-3 beta-(p-hydroxyphenyl)- trans-bicyclo[4.3.0]nonan-7 beta-ol (18) and their derivatives, which are essentially B-seco-steroids having cis-anti-trans, cis-syn-trans and trans-anti-trans geometries have been carried out. A study of their antiimplantation activities (AI) and receptor binding affinities (RBA) show that trans-anti-trans compounds are biologically most potent, followed by the corresponding cis-anti-trans and cis-syn-trans compounds. The most potent compound 18 is active at 1 mg/kg in rats. Introduction of 7 alpha-ethynyl group increases their AI activity; however, no significant effect on their RBA is observed.
（±）2α，6β-二乙基-7α-乙炔基-3α-（对羟基苯基）-反式双环[4.3.0]壬烷-7β-醇（8）、（±）2β，6β-二乙基-7α-乙炔基-3β-（对甲氧基苯基）-反式双环[4.3.0]壬烷-7β-醇12和（±）2α，6β-二乙基-7α-乙炔基-3β-（对羟基苯基）-反式双环[4.3.0]壬烷-7β-醇（18）及其衍生物的合成已经完成，这些化合物本质上是具有顺式-反式-反式、顺式-顺式-反式和反式-反式-反式几何结构的B-开环甾体。对它们的抗着床活性（AI）和受体结合亲和力（RBA）的研究表明，反式-反式-反式化合物在生物学上最具活性，其次是相应的顺式-反式-反式和顺式-顺式-反式化合物。最具活性的化合物18在大鼠体内1mg/kg剂量时具有活性。引入7α-乙炔基会增加它们的AI活性；然而，未观察到对其RBA有显著影响。
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