Syntheses and biologic studies of steroidal methyl sulfides and sulfones.
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.
Shafiullah
Department of Chemistry, Aligarh Muslim University, India.
Dua
P R
PR
Srimal
R C
RC
Ansari
S A
SA
D000818:Animals; D001341:Autonomic Nervous System / Q000187:drug effects*; D001794:Blood Pressure / Q000187:drug effects*; D002415:Cats; D002490:Central Nervous System / Q000187:drug effects*; D051379:Mice; D015394:Molecular Structure; D013256:Steroids / Q000138:chemical synthesis* / Q000494:pharmacology; D013440:Sulfides / Q000138:chemical synthesis* / Q000494:pharmacology; D013450:Sulfones / Q000138:chemical synthesis* / Q000494:pharmacology
D013256:Steroids; D013440:Sulfides; D013450:Sulfones