Synthesis and Antimicrobial Evaluation of (E)-2-(4-((4-((1-(2,4-Dichlorophenyl)-3-methyl-5-oxo-1,5-dihydro-4H-pyrazol-4-ylidene)methyl)-2-methoxyphenoxy)methyl)-1H-1,2,3-triazol-1-yl)-N-phenylacetamide Derivatives

Abstract

Objective: There has never been a compilation of (E)-2-(4-((4-((1-(2,4-dichlorophenyl)-3-methyl-5-oxo-1H-pyrazol-4(5H)-ylidene)methyl)-2-methoxyphenoxy)methyl)-1H-1,2,3-triazol-1-yl)-N-phenylacetamide derivatives produced before. For the synthesis of (VIIa–VIIh), (E)-1-(2,4-dichlorophenyl)-4-(3-methoxy-4-(prop-2-yn-1-yloxy)benzylidene)-3-methyl-1H-pyrazol-5(4H)-one (V) was utilized. Methods: The compounds were synthesized using the Click chemistry process. We used the tube-dilution approach to test for antimicrobial and antifungal activity. Results and Discussion: Mass spectrometry, ¹H, ¹³C NMR, and IR spectroscopy were used to validate the eight newly produced compounds. The antibacterial and antifungal properties of the new compounds were tested. While seven compounds ((VIIa–VIIc), (VIIe–VIIh)) demonstrated antimicrobial activity against a range of bacterial strains, including Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, and Streptococcus pyogenes, the activity was comparable to that of the drug ampicillin, whereas (VIIh) exhibited good antifungal activity compared to its standard drug Griseofulvin against Candida albicans. Conclusions: We conclude that the newly synthesized 1,2,3-triazoles showed good antibacterial activity and can be used as precursors for drug molecules in the future.