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Syntheses and biologic studies of steroidal methyl sulfides and sulfones
Shafiullah1, P R Dua, R C Srimal
1Department of Chemistry, Aligarh Muslim University, India.
Abstract:
Reactions of cholest-5-ene (I) and its 3 beta-chloro (II) and 3 beta-acetoxy (III) analogs with trimethylchlorosilane-dimethyl sulfoxide in dry acetonitrile furnish cholest-4-en-6 beta-yl methyl sulfide (IV) and its 3 beta-chloro (V) and 3 beta-acetoxy (VI) analogs. Oxidation of (IV) with m-chloroperbenzoic acid affords cholest-4-en-6 beta-yl methyl sulfone (VII) and 4 alpha, 5-epoxy-5 alpha-cholestan-6 beta-yl methyl sulfone (VIII). Under similar reaction conditions, V furnishes 3 beta-chlorocholest-4-en-6 beta-yl methyl sulfone (IX), while VI gives 3 beta-acetoxycholest-4-en-6 beta-yl methyl sulfone (X) and 3 beta-acetoxy-4 alpha, 5-epoxy-5 alpha-cholestan-6 beta-yl methyl sulfone (XI). The structures of these compounds were established on the basis of analytic and spectral data. Some of these compounds have been evaluated for their possible biologic activities.