Synthesis and Biological Evaluation of Some Novel 3,4-dichloroacetophenone Chalcones as Potential Antifungal, Anti Tubercular, and Cytotoxic Agents

Abstract

Chalcones containing a variety of rings were found to possess significant biological activities including antibacterial, antifungal, anti-inflammatory, anticancer, anti-HIV, antimalarial, anthelmintic, MAO inhibition, and anti-angiogenic activities. The present study was to synthesize a series of novel 3,4-dichloro acetophenone derivatives including chalcones by Claisen-Schmidt condensation, to characterize the synthesized chalcones using suitable IR, 1H NMR, 13C NMR, mass spectra and elemental analyses data, to screen the synthesized chalcones for their antifungal, anti-tubercular, and cytotoxic activities, to identify the active compounds for further exploitation. The composition of the synthesized compounds was confirmed by elemental analysis and the results were also in close agreement with those of the calculated values. Results of the antifungal activity clearly notify that the chalcones exhibited significant antifungal activity with altered MIC values against the tested organisms, but not as much of the standard fluconazole. The results of the anti-tubercular activity of novel chalcones 3a-3o divulged that all the compounds exhibited considerable activity against the M. tuberculosis H37Rv strain. The titled compounds (3a-3o) were evaluated for their in vitro cytotoxic activity against prostate cancer cell line DU-145 by using MTT assay. Most potent chalcone of the series was 3o containing 2”-thienyl rings at portion-B, with an of MIC 5µg/mL which is equal to that of the positive control methotrexate.