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 3beta-hydroxy-16alpha-(2-hydroxy ethoxy) pregn-5-en-20-one (5) was synthesized from 3beta-hydroxy-5,16-pregnadiene-20-one (2) by adopting general modified procedure using BF(3):Et(2)O as a catalyst. Reduction of 5, with sodium borohydride yielded 3beta,20beta-dihydroxy-16alpha-(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-3beta-hydroxy-pregn-5,16-diene (11). Synthesis of C-16 substituted pregnane glycosides (20) and (21) were accomplished with the imidate method using BF(3):Et(2)O. 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.
Sethi
Arun
A
Department of Chemistry, University of Lucknow, Lucknow 226007, India.
Maurya
Atul
A
Tewari
Vibha
V
Srivastava
Sanjay
S
Faridi
Shaheen
S
Bhatia
Gitika
G
Khan
M M
MM
Khanna
A K
AK
Saxena
J K
JK
D000818:Animals; D000975:Antioxidants / Q000138:chemical synthesis* / Q000494:pharmacology*; D002784:Cholesterol / Q000097:blood; D006027:Glycosides / Q000138:chemical synthesis / Q000494:pharmacology; D006949:Hyperlipidemias / Q000097:blood / Q000139:chemically induced / Q000188:drug therapy; D000960:Hypolipidemic Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D007202:Indicators and Reagents; D008297:Male; D008315:Malondialdehyde / Q000737:chemistry; D010743:Phospholipids / Q000097:blood; D011092:Polyethylene Glycols / Q000494:pharmacology; D011278:Pregnanes / Q000138:chemical synthesis* / Q000494:pharmacology*; D051381:Rats; D013481:Superoxides / Q000737:chemistry; D014280:Triglycerides / Q000097:blood
D000975:Antioxidants; D006027:Glycosides; D000960:Hypolipidemic Agents; D007202:Indicators and Reagents; D010743:Phospholipids; D011278:Pregnanes; D014280:Triglycerides; D013481:Superoxides; D011092:Polyethylene Glycols; D008315:Malondialdehyde; D002784:Cholesterol; C016811:tyloxapol