title: Synthesis and testing of 17a beta-hydroxy-7 alpha-methyl-D-homoestra-4,16-dien-3-one: a highly potent orally active androgen.
abstract: The title compound, 17a beta-hydroxy-7 alpha-methyl-D-homoestra-4,16-dien-3-one (3), was synthesized in five steps (17% overall yield) from 7 alpha-methylestrone methyl ether (5) and was found to possess oral androgenic activity, in excess of other known androgens, without using 17 alpha-alkyl substitution.
authors.affiliation: Life Sciences Division, SRI International, Menlo Park, CA 94025.
authors.forename: M A
authors.initials: MA
authors.lastname: Avery
authors.forename: M
authors.initials: M
authors.lastname: Tanabe
authors.forename: D F
authors.initials: DF
authors.lastname: Crowe
authors.forename: G
authors.initials: G
authors.lastname: Detre
authors.forename: R H
authors.initials: RH
authors.lastname: Peters
authors.forename: W K
authors.initials: WK
authors.lastname: Chong
mesh_terms: D000818:Animals; D055598:Chemical Phenomena; D002621:Chemistry; D003278:Contraceptives, Oral, Hormonal / Q000138:chemical synthesis* / Q000494:pharmacology*; D004963:Estrenes; D005298:Fertility / Q000187:drug effects; D006718:Homosteroids; D008297:Male; D051381:Rats; D011919:Rats, Inbred Strains; D045165:Testosterone Congeners / Q000138:chemical synthesis* / Q000494:pharmacology
chemical_list: D003278:Contraceptives, Oral, Hormonal; D004963:Estrenes; D006718:Homosteroids; D045165:Testosterone Congeners; C063630:17-hydroxy-7-methyl-D-homoestra-4,16-dien-3-one