Expeditious and convenient synthesis of pregnanes and its glycosides as potential anti-dyslipidemic and anti-oxidant agents

A series of new pregnane derivatives and its glycosides were synthesized in order to find new 'leads' against some important targets. The 3 beta-hydroxy-16 alpha-(2-hydroxy ethoxy) pregn-5-en-20-one (5) was synthesized from 3 beta-hydroxy-5,16-pregnadiene-20-one (2) by adopting general modified procedure using BF3:Et2O as a catalyst. Reduction of 5, with sodium borohydride yielded 3 beta,20 beta-dihydroxy-16 alpha-(2-hydroxy ethoxy) pregn-5-en (7) as the major isolable product. O-alkylation of the C-20-oxime-pregnadiene (9) with 1,5-dibromopentane yielded 20-(O-5-bromopentyl)-oximino-3 beta-hydroxy-pregn-5,16-diene (11). Synthesis of C-16 substituted pregnane glycosides (20) and (21) were accomplished with the imidate method using BF3:Et2O. The synthesis of 4-chlorobenzoate (3) and 2-chlorobenzoate (4), derivatives of 2 were also accomplished. These compounds were evaluated for their anti-dyslipidemic and anti-oxidant activity and amongst them compounds 3 and 7 showed more lipid lowering and anti-oxidant activity. (c) 2007 Elsevier Ltd. All rights reserved.