11 beta-nitrate estrane analogues: potent estrogens.
Various estrane derivatives 1 reacted with cerium ammonium nitrate (CAN) selectively and efficiently to provide 9 alpha,11 beta-defunctionalized derivatives 2, which were subsequently deoxygenated at C-9 with triethylsilane/boron trifluoride etherate to the desired target 11 beta-nitratoestranes 3a, 3b, and 5. When examined for estrogenic and postcoital antifertility activity, 11 beta-nitrates 2c, 2d, and 3b most notably displayed more potent oral activity than did ethynylestradiol.
Peters
R H
RH
Bio-Organic Chemistry Laboratory, SRI International, Menlo Park, California 94025.
Crowe
D F
DF
Avery
M A
MA
Chong
W K
WK
Tanabe
M
M
D000818:Animals; D003276:Contraceptives, Oral / Q000138:chemical synthesis*; D045166:Estradiol Congeners / Q000138:chemical synthesis*; D004962:Estranes / Q000138:chemical synthesis* / Q000494:pharmacology; D004997:Ethinyl Estradiol / Q000494:pharmacology; D005260:Female; D005836:Genitalia, Female / Q000033:anatomy & histology / Q000187:drug effects; D015394:Molecular Structure; D009566:Nitrates / Q000138:chemical synthesis / Q000494:pharmacology; D009929:Organ Size / Q000187:drug effects; D051381:Rats; D011919:Rats, Inbred Strains; D013329:Structure-Activity Relationship
D003276:Contraceptives, Oral; D045166:Estradiol Congeners; D004962:Estranes; D009566:Nitrates; D004997:Ethinyl Estradiol