Trans-dehidroepiandrosteron'dan benzimidazol sübstitüe trihidroksi steroidlerin sentezi

Azolyl steroids and oxysterols are important class of steroids which were reported to have possess variety of biological activities; anti-cancer, anti-apoptotic and some androgen-dependent diseases. 3β-Acetoxy-17-chloro-16-formylandrosta-5,16-diene was synthesised by using POCl3 and DMF with Vilsmeier-Haack reaction of 3β-hydroxyandrost-5-en-17-one. This reagent was used as starting materials for C-17-azolyl steroids (4a, 4b) and C-16 azolyl steroid (8) synthesis. The formyl group on 4a was then reduced with NaBH4 to the corresponding hydroxy compound 5 and m-chloroperoxybenzoic acid and was used to convert the double bond in B ring of 5 into cis-diols (3β-Acetoxy-17-(1H-benzimidazol-1-yl)-5,6-dihydroxy-16-(hydroxymethyl)-16-ene, 6). Different α,β-unsaturated tri-hydroxy aza-steroids (11a-c) were also synthesized from the reaction of α,β-unsaturated aza-steroids (10a-c) with m-chloroperoxybenzoic acid in dichloromethane. Synthesis of 3β,5α,6β-trihydroxy androstanone (12) was carried out from reaction of DHEA (1) and m-CPBA in dichloro methane. The hydroxyl groups on 12 were converted to acetoxy groups by acylation reaction to obtained 3β, 5α,6β-triacetoxyandrost-17-one (13). Keywords: Dehydroepiandrosterone (DHEA), benzimidazole, Vilsmeier-Haack reaction, m-CPBA, azolyl steroids