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New 1,3,5-triazine Derivatives Incorporating Aminobenzenesulfonamide, Aminoalcohol, Piperazine, Chalcone or Stilbene Structural Motifs and Evaluation of Their Antioxidative Activity
* 1 , 2 , 2 , 2 , 2 , 3
1  Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackého tř. 1, CZ-612 42 Brno, Czech Republic
2  Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Brno, Czech Republic
3  Centre for Syntheses at Sustainable Conditions and Their Management Department of Chemistry, Faculty of Science, Masaryk University, UKB, Kamenice 753/5, CZ-625 00 Brno, Czech Republic

Abstract:

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.

Keywords: 1,3,5-Triazine; Benzene sulfonamides; ABTS method; Antioxidants
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