Antidyslipidemic and antioxidative activities of 8-hydroxyquinoline derived novel keto-enamine Schiffs bases

8-Hydroxyquinoline when subjected to Duff reaction resulted in the formation of unexpected 7-methylaminomethylene-8-oxo-7, 8-dihydroquinoline-5-carbaldehyde 2, which existed in the keto-enamine form, in which the aromaticity of the relevant ring was disrupted, which upon subsequent treatment with various primary amines resulted in its nucleophilic substitution of aliphatic methyl amine. These interesting novel derivatives were evaluated in vitro for their antioxidant and in vivo for their antidyslipidemic and post-heparin lipolytic activities. Compound 6 was found to be most active antidyslipidemic and antioxidative agent in this series, respectively, and thus represent a new class of promising lead.

Graphical abstractA novel series of keto-enamine Schiff bases have been synthesized from 8-hydroxyquinoline following an uncommon method and evaluated for antidyslipidemic and post-heparin lipolytic activities in vivo and antioxidant activity in vitro. Compound 6 represents a new class of promising lead.Figure optionsDownload full-size imageDownload as PowerPoint slide