New 1,3,5-triazine Derivatives Incorporating Aminobenzenesulfonamide, Aminoalcohol, Piperazine, Chalcone or Stilbene Structural Motifs and Evaluation of Their Antioxidative Activity

A series of 1,3,5-triazine derivatives, incorporating aminobenzenesulfonamide, aminoalcohol, piperazine, chalcone, or stilbene structural motifs were evaluated as potential antioxidants. The compounds were prepared by using step by step nucleophilic substitution of chlorine atoms in starting 2,4,6-trichloro-1,3,5-triazine. Reactions were catalyzed by Cu(I)-supported on a weakly acidic resin. The radical scavenging activity was determined in terms of %inhibition activity and IC₅₀, using the ABTS method. Trolox and ascorbic acid (ASA) were used as standards. In the lowest used concentration 1x10^-4 M, the %inhibition activity at time 0 min was comparable with both standards at least for 10 compounds. After 60 min compounds 1, 2, 9 and 25 showed nearly twice %inhibition (73.44 – 87.09 %) in comparison with standards (Trolox = 34.96 %; ASA = 29.09 %). Values of IC₅₀ correlated with %inhibition activity. For compounds 1, 2, 9 and 25 values of IC₅₀ in time 60 min (17.16 – 27.78 μM) were 5 times lower than IC₅₀ of both standards (Trolox = 178.33 μM; ASA = 147.47 μM). Based on these results, the presented 1,3,5-triazine derivatives and their analogs have a high potential in the treatment of illnesses caused or related to oxidative stress.