title: Synthesis of novel 6-aza-B- and 11-aza-C-homoestranes as antifertility agents.
abstract: Reaction of 3,9 alpha, 17 beta-trihydroxyestra-1,3,5(10)-trien-11-one 17-acetate 3-methyl ether (3) with N3H-BF3 etherate leads mainly to lactam (4) along with the N-azido compound (5) as a minor product. Under similar conditions, 3,17 beta-dihydroxyestra-1,3,5(10)-trien-6-one 17-acetate 3-methyl ether gives lactam (12) and the tetrazole derivative (9). Similar reaction of the diacetate (8) gives only the tetrazole derivative (11). Compounds 4, 6, and 10 prevent implantation in rats at 5-, 10-, and 5-mg/kg doses, respectively. Compounds 4, 6, 9, and 10 show significant estrogenic activity at the respective contraceptive doses.
authors: Medicinal Chemistry Division, Central Drug Research Institute, Lucknow, India.
authors: I
authors: I
authors: Dwivedy
authors: A K
authors: AK
authors: Singh
authors: M M
authors: MM
authors: Singh
authors: S
authors: S
authors: Ray
mesh_terms: D000818:Animals; D001378:Azasteroids / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D003271:Contraceptive Agents, Female / Q000138:chemical synthesis*; D010064:Embryo Implantation / Q000187:drug effects; D004962:Estranes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D005260:Female; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D051381:Rats
chemical_list: D001378:Azasteroids; D003271:Contraceptive Agents, Female; D004962:Estranes