3,17 beta-Dihydroxy-20,21-epoxy-19-norpregna-1,3,5(10)-trienes: synthesis, rearrangement, cytotoxicity, and estrogen-receptor binding.
Diastereoisomers of 3,17 beta-dihydroxy-20,21-epoxy-19-norpregna-1,3,5(10)-triene have been prepared as potential antitumor agents. Both isomers undergo the base-catalyzed Payne rearrangement. The isomers were cytotoxic to mammalian cells in culture and were able to displace [3H]estradiol from binding sites in rat uterine cytosols with 1/7 and 1/70 the potency of estradiol. The reasons for this difference are discussed.
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000378:metabolism; D002470:Cell Survival / Q000187:drug effects; D004958:Estradiol / Q000378:metabolism; D005260:Female; D009651:Norpregnatrienes / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D051381:Rats; D011960:Receptors, Estrogen / Q000378:metabolism*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014599:Uterus / Q000187:drug effects / Q000378:metabolism
D000970:Antineoplastic Agents; D009651:Norpregnatrienes; D011960:Receptors, Estrogen; C049796:3,17-dihydroxy-20,21-epoxy-19-norpregna-1,3,5(10)-triene; D004958:Estradiol