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Open AccessArticle

Antioxidative Activity of 1,3,5-Triazine Analogues Incorporating Aminobenzene Sulfonamide, Aminoalcohol/Phenol, Piperazine, Chalcone, or Stilbene Motifs

1
Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, 612 42 Brno, Czech Republic
2
Department of Chemistry, Faculty of Science, Centre for Syntheses at Sustainable Conditions and Their Management, Masaryk University, 625 00 Brno, Czech Republic
*
Author to whom correspondence should be addressed.
Molecules 2020, 25(8), 1787; https://doi.org/10.3390/molecules25081787
Received: 6 March 2020 / Revised: 31 March 2020 / Accepted: 9 April 2020 / Published: 14 April 2020
(This article belongs to the Special Issue ECSOC-23)
A series of 1,3,5-triazine analogues, incorporating aminobenzene sulfonamide, aminoalcohol/phenol, 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 EC50, using the ABTS method. Trolox and ascorbic acid (ASA) were used as standards. In the lowest concentration 1 × 10−4 M, the %inhibition activity values at 0 min were comparable with both standards at least for 10 compounds. After 60 min, compounds 5, 6, 13, and 25 showed nearly twice %inhibition (73.44–87.09%) in comparison with the standards (Trolox = 41.49%; ASA = 31.07%). Values of EC50 at 60 min (17.16–27.78 μM) were 5 times lower for compounds 5, 6, 13, and 25 than EC50 of both standards (trolox = 178.33 μM; ASA = 147.47 μM). Values of EC50 correlated with %inhibition activity. Based on these results, the presented 1,3,5-triazine analogues have a high potential in the treatment of illnesses caused or related to oxidative stress. View Full-Text
Keywords: 1,3,5-triazine; 4-aminophenol; hydroxychalcone; hydroxystilbene; antioxidative activity; ABTS method 1,3,5-triazine; 4-aminophenol; hydroxychalcone; hydroxystilbene; antioxidative activity; ABTS method
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MDPI and ACS Style

Havránková, E.; Čalkovská, N.; Padrtová, T.; Csöllei, J.; Opatřilová, R.; Pazdera, P. Antioxidative Activity of 1,3,5-Triazine Analogues Incorporating Aminobenzene Sulfonamide, Aminoalcohol/Phenol, Piperazine, Chalcone, or Stilbene Motifs. Molecules 2020, 25, 1787.

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