title: Synthesis and estrogenic properties of 7 alpha,8 alpha-epoxy- and 7 alpha, 8 alpha-methyleneestradiols.
abstract: A series of 7alpha,8alpha-expoxyestradiol derivatives with ethynyl, 2- or 3-furyl, or 2-thienyl substituents in the 17alpha position was prepared. The products were highly active orally in the Allen-Doisy test in rats, but most of them were only weakly active in the uterotrophic assay in the mouse. A 7alpha,8alpha-methylene analog and a 7alpha,8alpha-difluormethylene analog were less active than the corresponding epoxides.
mesh_terms: D000818:Animals; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis / Q000494:pharmacology; D002369:Castration; D004852:Epoxy Compounds / Q000138:chemical synthesis / Q000494:pharmacology; D004958:Estradiol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D004967:Estrogens / Q000138:chemical synthesis* / Q000494:pharmacology; D005260:Female; D051379:Mice; D009929:Organ Size; D051381:Rats; D013329:Structure-Activity Relationship; D014599:Uterus / Q000187:drug effects
chemical_list: D001952:Bridged-Ring Compounds; D004852:Epoxy Compounds; D004967:Estrogens; D004958:Estradiol