Synthesis, In Vitro Antioxidant and Antimicrobial Activities of Some New 2-(3-Alkyl/Aryl-4,5-dihydro-1H-1,2,4-triazol-5-on-4-yl-azomethine)phenyl Benzenesulfonate Derivatives

Eight new 2-(3-alkyl/aryl-4,5-dihydro-1H-1,2,4-triazol-5-on-4-yl-azomethine)phenyl benzenesulfonates (3) were obtained by the reactions of 3-alkyl(aryl)-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones (1) with 2-benzenesulfonyloxybenzaldehyde (2). Moreover, eight N-acetyl derivatives (4) of compounds 3 were obtained. Then, seven new 2-[1-(morpholine-4-yl-methyl)-3-alkyl/aryl-4,5-dihydro-1H-1,2,4-triazol-5-on-4-yl-azomethine)phenyl benzenesulfonates (5) were obtained by the reactions of compounds 3 with formaldehyde and morpholine. The structures of twenty-three newly synthesized compounds were established from infrared, 1H-NMR, 13C-NMR, MS and UV spectral data. In addition, 3, 4 and 5 type compounds were examined for their in vitro potential antioxidant and antibacterial activities. Three different methods were used for the antioxidant assay and the compounds 5 showed a significant activity for iron-binding. Antimicrobial activity was determined on six bacteria using the agar well diffusion method