title: Synthesis and pregnancy-inhibiting activity of 7-substituted androst-5-ene derivatives.
abstract: Synthesis of 7-aryl/allyl-substituted androstene derivatives 3a through 3g has been carried out by Grignard reaction on 3 beta,17 beta-diacetoxyandrost-5-en-7-one (2) with aryl/allyl magnesium bromide. Isomeric mixture of products 3b and 3c/3e and 3f/3h was separated by column chromatography. Stereochemical assignment at C-7 has been made on the basis of 13C nuclear magnetic resonance studies and chemical considerations. Compounds 6a and 6b were synthesized by alkylation of compound 5 with beta-(N,N-diethylamino)ethyl chloride hydrochloride and 1-(2-chloroethyl)pyrrolidine hydrochloride, respectively. Compound 3g (isomeric mixture) prevented pregnancy in 60% of rats at 10 mg/kg daily dose administered orally on days 1 to 7 of pregnancy; however, its only isolable 7 beta-hydroxy isomer, 3h, was inactive at this dose.
authors.affiliation: Medicinal Chemistry Division, Central Drug Research Institute, Lucknow, India.
authors.forename: A
authors.initials: A
authors.lastname: Grover
authors.forename: I
authors.initials: I
authors.lastname: Dwivedy
authors.forename: A K
authors.initials: AK
authors.lastname: Singh
authors.forename: S
authors.initials: S
authors.lastname: Ray
authors.forename: M M
authors.initials: MM
authors.lastname: Singh
authors.forename: V P
authors.initials: VP
authors.lastname: Kamboj
mesh_terms: D000736:Androstenes / Q000138:chemical synthesis* / Q000494:pharmacology; D003270:Contraceptive Agents / Q000737:chemistry* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy
chemical_list: D000736:Androstenes; D003270:Contraceptive Agents