Synthesis and antioxidant, cytotoxicity and antimicrobial activities of novel curcumin mimics

Abstract

Claisen-Schmidt condensation of 3-(1,2,3,6-tetrahydro-1-methylpyridin-4-yl)-2,4,5- trimethoxybenzaldehyde 3 and various aromatic, heterocyclic and alicyclic amides of 3- aminoacetophenone 6(a–s) afforded novel curcumin mimics. All the synthesized compounds were characterized by IR, ¹H NMR, Mass spectroscopy and evaluated for antioxidant, cytotoxicity and antimicrobial activity. Out of the 20 compounds screened, compounds 7i, 7l, 7q, and 7n have shown excellent radical scavenging activity, compounds 7o, 7t, 7f, and 7r have shown significant xanthine oxidase inhibition, and compounds 7a, 7k and 7l were found to be potent inhibitors of selected cancer cell lines. Compounds 7h, 7t, 7l, 7i, and 7e have shown good antibacterial activity, whereas compounds 7j, 7f, 7o, 7h, and 7t exhibited significant antifungal activity.

Keywords::

• Curcumin mimics
• antioxidant
• xanthine oxidase
• cytotoxicity
• antimicrobial

Acknowledgments

HVC is thankful to the Council of Scientific and Industrial Research (CSIR), New Delhi, for the award of JRF, as well as to Mahesh Nambiar and Mrs Asha Almeida Piramal Life Sciences Ltd., Mumbai, for anticancer activity.

Declaration of interest

The authors report no conflicts of interest.