Synthesis and biological evaluation of naphthalene, furan and pyrrole based chalcones as cytotoxic and antimicrobial agents

Chalcone is an aromatic ketone that forms the central core for a variety of important biological compounds, which are collectively known as chalcones. These show antibacterial, antifungal, antitumour and anti-inflammatory properties, and also are intermediates in the biosynthesis of flavonoids, substances widespread in plants with an array of biological activities. These biaryl propenones show potent toxicity to several cancer cell lines and interact with tubulin at its colchicine-binding site. Tubulin binding molecules interfere with the dynamic instability of microtubules and thereby disrupt microtubule inducing cell cycle arrest in the M phase, forming abnormal spindles and finally leading to apoptotic cell death. Basically Chalcones consists of C 6 –C 3 –C 6 units but in the present study we report the reactions of 1-acetylnaphthalene, 2-acetylfuran and 2-acetylpyrrole with aldehydes, thus getting compounds akin to chalcones. 31 analogues have been synthesised and evaluated for cytotoxic potential against PC-3, OVCAR, IMR-32 and HEP-2. Compound 9 was found to be the most cytotoxic with inhibition ranging from 72 to 88% against the cell lines employed. The synthetics were also evaluated for antimicrobial activity and compound 25 was found to be the most potent. Graphical Abstract 31 Analogues of chalcones were synthesized and evaluated for in vitro cytotoxicity against PC-3, OVCAR, IMR-32 and HEP-2 human cancer cell lines as well as antimicrobial activity against five reference bacterial strains and two fungal strains. Napthone proved to be the most potent synthone for both cytotoxic as well as antimicrobial activity.