Design, synthesis, characterization of some new 1,2,3-triazolyl chalcone derivatives as potential anti-microbial, anti-oxidant and anti-cancer agents via a Claisen–Schmidt reaction approach

Abstract

The synthesis of a new series of (2E)-1-{1-[2,3-dichloro-6-methyl-5-(trifluoromethyl)phenyl]-5-methyl-1H-1,2,3-triazol-4-yl}-3-aryl prop-2-en-1-one (5a–k) and (2E)-1-{1-[2,3-dichloro-6-methyl-5-(trifluoromethyl)phenyl]-5-methyl-1H-1,2,3-triazol-4-yl}-3-(1,3-diaryl-1H-pyrazol-4-yl)prop-2-en-1-one (6a–e) were carried out via a Claisen–Schmidt condensation of 1-{1-[2,3-dichloro-6-methyl-5-(trifluoromethyl)phenyl]-5-methyl-1H-1,2,3-triazol-4-yl}ethanone (4) with different aryl and 1,3-diaryl-1H-pyrazole-4-carbaldehydes iii(a-e) in the presence of ethanol and aqueous sodium hydroxide mixture respectively. The newly synthesized compounds were characterized by IR, ¹H NMR, ¹³C NMR, mass spectral data and elemental analysis. Further, they were screened for their in vitro anti-microbial, anti-oxidant and anti-cancer activities. Most of the synthesized compounds were displayed broad spectrum of anti-microbial, anti-oxidant activities and some of them exhibits moderate to excellent anti-cancer activities on breast cancer cell lines. Overall, this work has contributed to the development of promising leads for anti-microbial, anti-oxidant and anti-cancer activities.