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Synthesis and pregnancy-inhibiting activity of 7-substituted androst-5-ene derivatives

Grover, A.; Dwivedy, I.; Singh, A.K.; Ray, S.; Singh, M.M.; Kamboj, V.P.

Steroids 56(9): 477-480

1991

ISSN/ISBN: 0039-128X
PMID: 1805460
DOI: 10.1016/0039-128x(91)90005-g
Document Number: 318038
12 new C-7 aryl- and allyl-substituted androst-5-ene derivatives were synthesized, characterized, and were screened for anti-implantation activity in rats. 10 compounds were constructed by linking the aryl/allyl magnesium bromide with 3-beta, 17-beta-diacetoxyandrost-5-en-7-one by a Grignard reaction, and 2 further compounds were made by alkylation. Isomeric mixtures were separated by column chromatography, and stereochemical assignment at C-7 determined by nuclear magnetic resonance and chemical characteristics. The isomeric mixture of the N-N-dimethyl aminophenyl derivative prevented pregnancy in 6 of 10 rats tested at a 10 mg/kg dose p.o., given on Days 1-7 after coitus. The pure 7-beta-OH isomer was inactive, and the 7-alpha-OH isomer could not be obtained from column chromatography on neutral alumina.

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