Design, Synthesis and In Vitro Biological Assessment Of Novel 2-[(3-Alkyl/Aryl-4,5-Dihydro-1h-1,2,4-Triazol-5-One-4-Yl)Azomethine]Phenyl 2,5-Dichlorobenzenesulfonates Molecules as Antioxidant and Antibacterial Agents

Abstract

In this study, a total of nine new 2-[(3-alkyl/aryl-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl)azomethine]phenyl 2,5-dichlorobenzenesulfonates (4a-i) were synthesized through the reactions of 2-formylphenyl 2,5-dichlorobenzenesulfonate (3) with 3-alkyl(aryl)-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones (2a-i). The compounds 4a, 4e, 4g and 4h were successfully synthesized with yields exceeding 90%. Compounds 4a-i were elucidated using 1H, 13C NMR and IR spectroscopic methods. The spectroscopic data were compared with the literature, and the results were found to be consistent. The antioxidant effects of compounds 4a–i were investigated using three different methods, and it was found that compounds 4a-i showed metal chelation activity close to that of α-tocopherol, which was used as the standard. Additionally, the antimicrobial properties of the compounds 4a–i were evaluated using the agar well diffusion method against six different bacterial strains. The antimicrobial properties of the new compounds (4a-i) were compared with those of standard antibiotics such as neomycin, streptomycin, and ampicillin. It was observed that compound 4a exhibited better antimicrobial activity than neomycin and streptomycin, and comparable activity to ampicillin.