Synthesis and testing of 17a beta-hydroxy-7 alpha-methyl-D-homoestra-4,16-dien-3-one: a highly potent orally active androgen.
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.
Avery
M A
MA
Life Sciences Division, SRI International, Menlo Park, CA 94025.
Tanabe
M
M
Crowe
D F
DF
Detre
G
G
Peters
R H
RH
Chong
W K
WK
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
D003278:Contraceptives, Oral, Hormonal; D004963:Estrenes; D006718:Homosteroids; D045165:Testosterone Congeners; C063630:17-hydroxy-7-methyl-D-homoestra-4,16-dien-3-one