Oxidation of furans. 3. Estrogenic properties of lactones and anhydrides derived from the oxidation of 17alpha-[3-furyl]estradiol derivatives.
The oxidation of 17alpha-[3-furyl]estradiol derivatives and the estrogenic properties of the resulting isomeric 17,21-and 17,23-dihydroxy-19,24-dinor-17alpha-chola-1,3,5(10)20(22)-tetraenoic acid(20leads to 23) gamma-lactones as well as those of the related 17-hydroxy-19-nor-17alpha-pregna-1,3,5(10)-triene-20,21-dicarboxylic acid anhydrides and gamma-lactones are described. Of these, only lactones 3c,e,h and 5b retained the same degree and profile of estrogenic activity as the starting 17alpha-[3-furyl]estradiols.
D000812:Anhydrides / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D002770:Cholenes / Q000138:chemical synthesis / Q000494:pharmacology; D004958:Estradiol / Q000031:analogs & derivatives* / Q000494:pharmacology; D045166:Estradiol Congeners / Q000138:chemical synthesis* / Q000494:pharmacology; D005260:Female; D005663:Furans; D007783:Lactones / Q000138:chemical synthesis* / Q000494:pharmacology; D051379:Mice; D009654:Norsteroids / Q000138:chemical synthesis / Q000494:pharmacology; D051381:Rats; D013268:Stimulation, Chemical; D014599:Uterus / Q000187:drug effects
D000812:Anhydrides; D002770:Cholenes; D045166:Estradiol Congeners; D005663:Furans; D007783:Lactones; D009654:Norsteroids; D004958:Estradiol