AI Article Synopsis
- The synthesis of 7-aryl/allyl-substituted androstenes (3a-3g) involved a Grignard reaction on a specific precursor compound, resulting in an isomeric mixture that was separated using column chromatography.
- Stereochemical assignment at carbon position C-7 was confirmed through 13C NMR studies and other chemical analysis methods.
- The compound 3g showed potential anti-pregnancy effects in rats, while its isolated isomer 3h was found to be ineffective at the same dosage.
Article 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.
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| http://dx.doi.org/10.1016/0039-128x(91)90005-g | DOI Listing |
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