Synthesis and antifertility activity of 3,9-dihydroxy-5,6,6a alpha,6b beta,11,12,12a beta,12b alpha-octahydrodibenzo[a,g]biphenylene, a structural relative of diethylstilbestrol.
The title diphenol, 1a, was synthesized from p,p'-dihydroxy-alpha-truxillic acid and shown to be active as an oral postcoital antifertility agent in rats: ED100 = 100 (micrograms/kg)/day. The oral uterotropic potency was estimated to be 16% of that of diethylstilbestrol (95% confidence limits of potency 8--35%). The structure of the diphenol, 1a, was confirmed by single-crystal X-ray analysis of the dimethyl ether.
D000818:Animals; D000970:Antineoplastic Agents; D055598:Chemical Phenomena; D002621:Chemistry; D003281:Contraceptives, Postcoital / Q000138:chemical synthesis*; D003283:Contraceptives, Postcoital, Synthetic / Q000138:chemical synthesis*; D005260:Female; D008297:Male; D009284:Naphthols / Q000138:chemical synthesis* / Q000494:pharmacology; D009929:Organ Size / Q000187:drug effects; D051381:Rats; D014599:Uterus / Q000187:drug effects
D000970:Antineoplastic Agents; D003281:Contraceptives, Postcoital; D003283:Contraceptives, Postcoital, Synthetic; D009284:Naphthols; C028345:3,9-dihydroxyoctahydrodibenzo(a,g)biphenylene