11 beta-nitrate estrane analogues: potent estrogens.

Basic Information

ID: ALA1124653

Journal: J Med Chem

Title: 11 beta-nitrate estrane analogues: potent estrogens.

Authors: Peters RH, Crowe DF, Avery MA, Chong WK, Tanabe M.

Abstract: 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.

CiteXplore: 2795603

DOI: 10.1021/jm00130a014

Patent ID: