Synthesis, Antimicrobial Activity, and Molecular Docking Study of Novel (E)-1-(5-Chloro-2-hydroxyphenyl)-3-{5-fluoro-2-[(1-phenyl-1H-1,2,3-triazol-4-yl)methoxy]phenyl}-prop-2-en-1-one Derivatives

In the search for new active compounds, a small, focused library of novel molecular hybrids of chalcone tethered 1,2,3-triazole derivatives has been effectively synthesized via the click chemistry approach. A total of 17 newly synthesized compounds were validated by using mass spectrometry, 1H, 13C NMR and IR spectroscopy. The antibacterial and antifungal activities of the novel compounds were screened against the four bacterial strains of Pseudomonas aeruginosa, Staphylococcus aureus, Escherichia coli and Streptococcus pyogenes and three fungal strains of Candida albicans, Aspergillus niger and Aspergillus clavatus. Some of the compound exhibited equipotent antibacterial activity against the standard drug chloramphenicol while rest of the compounds exhibited good to moderate activity against chloramphenicol. The antifungal activity of few compounds having MIC value 250 mu g/mL were found to be two-fold more active to the standard drug Griseofulvin, while some with MIC value 500 mu g/mL were comparable when compared to Griseofulvin. Furthermore, the synthesized compounds were also evaluated for them in silico and ADME properties as well as investigation in molecular modeling could confirm these findings by indicating extremely high binding affinities at the active site of the DNA gyrase, highlighting the scaffold's potential for future improvement. Thus, it can be concluded that by these findings the novel synthesized chalcone-triazole molecules can be used as a starting point for more potent antimicrobial agents in the future.