Click Chemistry-Mediated Synthesis, Spectroscopic Characterization, and Antimicrobial Evaluation of a Benzyl-Substituted 1,2,3-Triazole
TL;DR
The observed antimicrobial activity is attributed to the synergistic contribution of the 1,2,3-triazole nucleus, benzyl substituent, and electron-withdrawing nitrophenoxy moiety, which provide a promising pharmacophoric framework and warrant further structural optimization and mechanistic investigations.
Abstract
The increasing prevalence of antimicrobial resistance has intensified the search for new compounds with improved biological activity. In this study, 1,2,3-triazole derivative, 1-benzyl-4-((4-nitrophenoxy)methyl)-1H-1,2,3-triazole (PNT), was synthesized via a copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC) reaction and characterized using Fourier-transform infrared spectroscopy (FTIR), ultraviolet-visible (UV–Vis) spectroscopy, 1H and 13C nuclear magnetic resonance (NMR) spectroscopy, and high-resolution mass spectrometry (HRMS). The antimicrobial potential of PNT was evaluated against six bacterial (Staphylococcus aureus, Streptococcus pyogenes, Streptococcus faecalis, Escherichia coli, Salmonella typhi, and Klebsiella pneumoniae) and two fungal (Candida albicans and Aspergillus fumigatus) strains using the agar well diffusion method, followed by determination of the minimum inhibitory concentration (MIC), minimum bactericidal concentration (MBC), and minimum fungicidal concentration (MFC). The compound exhibited concentration-dependent antimicrobial activity, with the largest inhibition zone observed against Klebsiella pneumoniae (18.00 ± 0.26 mm at 100 μg/mL), while Aspergillus fumigatus was the most susceptible fungal isolate (17.00 ± 0.56 mm). MIC/MBC values of 1.56 μg/mL were obtained against Staphylococcus aureus, whereas MIC/MFC values of 1.56 μg/mL were recorded for Aspergillus fumigatus, indicating bactericidal and fungicidal activities at the inhibitory concentration. Activity index analysis further demonstrated appreciable relative antimicrobial efficacy, with values of 44.0% and 43.5% against Aspergillus fumigatus and Staphylococcus aureus, respectively. The observed antimicrobial activity is attributed to the synergistic contribution of the 1,2,3-triazole nucleus, benzyl substituent, and electron-withdrawing nitrophenoxy moiety, which provide a promising pharmacophoric framework. These findings identify PNT as a promising lead compound for the development of new triazole-based antimicrobial agents and warrant further structural optimization and mechanistic investigations.