Synthesis and Evaluation of Some Novel Pregnane Derivatives as Anti-Hyperlipidemic and Anti-Oxidant Agents

Author(s): Arun Sethi*, Akriti Bhatia, Ranvijay Pratap Singh, Atul Srivastava.

Journal Name: Letters in Organic Chemistry

Volume 16 , Issue 1 , 2019

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Abstract:

In the present paper, synthesis of few novel pregnane derivatives and their evaluation as potential anti-hyperlipidemic and anti-oxidant agents has been reported. The synthesis of 3β-hydroxy- 16α-methoxy pregn-5-en-20-one (4) was achieved by reaction of 3β-hydroxy-5,16-pregnadiene-20-one (3) with KOH/MeOH under reflux. Compound 4 on treatment with succinic and phthalic anhydride afforded compound 6 and 7, respectively. The reaction of the C-20-oxime-pregnadiene (8) with 1,5- dibromohexane yielded 20-(O-6-bromo hexyl)-oximino-3β-hydroxy-pregn-5, 16-diene (9). A novel heterocyclic derivative 3β-hydroxy-androst-5-en [17,16-c]-2′-methyl-7′ bromo-3′,4′-dihydro quinoline (16) was synthesized by reaction of 3 with 3-bromoaniline. However, attempted synthesis of other heterocyclic derivatives by reaction of (3) with other halogenated amine led to Aza-Michael addition products (10-14). The synthesized compounds were also evaluated for their anti-hyperlipidemic and anti-oxidant activities. Compounds 6 and 14 were found to exhibit more lipid lowering and antioxidant activities in comparison to other compounds.

Keywords: Pregnane, Aza-Michael addition, intramolecular condensation, anti-hyperlipidemic, anti-oxidant, steroid.

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Article Details

VOLUME: 16
ISSUE: 1
Year: 2019
Page: [40 - 49]
Pages: 10
DOI: 10.2174/1570178615666180806123719
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