Synthesis and biological properties of 17 alpha-furylestradiol and dihydroequilin derivatives.
A series of 17alpha-furylestradiol and dihydroequilin derivatives was synthesized by reacting the appropriate 3-substituted estrone and equilin with 2- or 3-furyllithium. The oral estrogenic activity of the compounds was compared with that of mestranol. In the Allen-Doisy test, the 17alpha-(3-furyl) analogs were 4-19 times as potent orally as the standard in rats but they were less active in mice. Acetylation of the 17-alcohol or replacement of the 3-furyl by a 2-furyl group produced a decrease in activity. In the mouse uterotrophic assay in mice the compounds were less effective than mestranol and exhibited very shallow dose-response curves.
D015068:17-Ketosteroids / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D004305:Dose-Response Relationship, Drug; D004958:Estradiol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D004962:Estranes / Q000138:chemical synthesis* / Q000494:pharmacology; D005260:Female; D005663:Furans / Q000138:chemical synthesis / Q000494:pharmacology; D006914:Hydroxysteroids / Q000138:chemical synthesis / Q000494:pharmacology; D051379:Mice; D009929:Organ Size; D051381:Rats; D013329:Structure-Activity Relationship; D014599:Uterus / Q000187:drug effects
D015068:17-Ketosteroids; D004962:Estranes; D005663:Furans; D006914:Hydroxysteroids; D004958:Estradiol