Antioxidant activity of a series of previously described 5-amino-N-(iododi(per)fluoroalkyl)-1H-1,2,3-triazole-4-carboxamides 3a-r, their synthetic precursors 5-amino-N-allyl-1,2,3-triazole-4-carboxamides 1a-g, and their deamination products N-(3-di(per)fluoroalkyl-2-iodo-n-propyl)-1,2,3-triazole-4-carboxamides 4a-e was investigated in vitro using DPPH test and ascorbic acid as a standard reference. It was established that compounds 3a-r inhibit DPPH free radicals in moderate to high values (50.9–97.6%). The effect of substituents in the position 1 of the 1,2,3-triazole nucleus, fluoroalkyl groups and amino groups on the level of antioxidant activity was studied in detail. Reactivity and electrostatic surface potential were evaluated for the most active carboxamides 3a,g,r using the DFT method, and molecular docking was studied in the NADPH oxidase protein model.