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

Abstract

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 antiinflammatory 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.

Coumarin moiety can enhance abilities of chalcones to inhibit DNA oxidation and to scavenge radicals

“…Especially, 4-methylcoumarin is a popular scaffold for constructing novel antioxidants. 11e13 On the other hand, chalcones also possess various biological properties 14 including antioxidant 15 and anticancer activities, 16 and are usually applied as a basic structure for preparing novel antioxidants. 17 In our previous work, we found that the inhibitory effect of 4-methylcoumarin on the radical-mediated oxidation of DNA can be increased by the moiety of 4,5-dihydropyrazole.…”

2,4-Diarylpyrano[3,2-<i>c</i>]chromen-5(4<i>H</i>)-ones as Antiproliferative Agents:

“…Cells were grown in a CO 2 incubator (Thermocon Electron Corporation, Waltham, MA, U.S.A.) at 37°C in an atmosphere of 95% air and 5% CO 2 with 98% humidity. Different derivatives of a coumarin-chalcone hybrid series (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20) were dissolved in 0.1% dimethyl sulfoxide (DMSO) and delivered to cell culture in complete medium.…”

“…12) Chemically, chalcones (1,3-diaryl-2-propen-1-ones) possess an enone bridge between two aromatic rings. 13) Chalcones have been one of the most extensively explored class possesing anticancer potential owing to their ease of synthesis and relatively simpler chemical architecture. Chalcone based hybrids have gained enough attention in the recent past as the presence of chalcones in various hybrid scaffolds has been evidenced through number of reports.…”

Synthesis and antimicrobial properties of N-substituted derivatives of (E)-2′,3″-thiazachalcones

“…These compounds have been reported to possess several biological activities, such as cytotoxic, antimalarial, antileishmanial, antiinflammatory, anti-HIV, antifungal [9][10][11][12][13][14][15][16][17]. Further, the preparation of furan and thiophene analogues of azachalcones has been described, and some of them have been found to possess a wide variety of biological activities, including antituberculosis, antimicrobial, antioxidant, antiinflammatory and antibacterial properties [15][16][17][18][19][20][21][22][23][24].…”