title: 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.
abstract: 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.
mesh_terms: D000818:Animals; D001667:Binding, Competitive; D055598:Chemical Phenomena; D002621:Chemistry; D003271:Contraceptive Agents, Female / Q000138:chemical synthesis* / Q000378:metabolism; D010064:Embryo Implantation / Q000187:drug effects; D004958:Estradiol / Q000378:metabolism; D005260:Female; D066298:In Vitro Techniques; D051381:Rats; D011960:Receptors, Estrogen / Q000378:metabolism; D012632:Secosteroids / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D013237:Stereoisomerism
chemical_list: D003271:Contraceptive Agents, Female; D011960:Receptors, Estrogen; D012632:Secosteroids; D004958:Estradiol