Synthesis and Antioxidant Activity of -Benzyl-2-[4-(aryl)-1-1,2,3-triazol-1-yl]ethan-1-imine Oxides.

The synthesis, antioxidant capacity, and anti-inflammatory activity of four novel -benzyl-2-[4-(aryl)-1-1,2,3-triazol-1-yl]ethan-1-imine oxides - are reported herein. The nitrones - were tested for their antioxidant properties and their ability to inhibit soybean lipoxygenase (LOX). Four diverse antioxidant tests were used for in vitro antioxidant assays, namely, interaction with the stable free radical DPPH (1,1-diphenyl-2-picrylhydrazyl radical) as well as with the water-soluble azo compound AAPH (2,2'-azobis(2-amidinopropane) dihydrochloride), competition with DMSO for hydroxyl radicals, and the scavenging of cationic radical ABTS (2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonate) radical cation). Nitrones , and , having the 4-fluorophenyl, 2,4-difluorophenyl, and 4-fluoro-3-methylphenyl motif, respectively, exhibited high interaction with DPPH (64.5-81% after 20 min; 79-96% after 60 min), whereas nitrone with unfunctionalized phenyl group showed the lowest inhibitory potency (57% after 20 min, 78% after 60 min). Nitrones and , decorated with phenyl and 4-fluoro-3-methylphenyl motif, respectively, appeared the most potent inhibitors of lipid peroxidation. The results obtained from radical cation ABTS were not significant, since all tested compounds - showed negligible activity (8-46%), much lower than Trolox (91%). Nitrone , bearing the 2,4-difluorophenyl motif, was found to be the most potent LOX inhibitor (IC = 10 μM).