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

Abstract

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.

Novel 1,3,5-Triazinyl Aminobenzenesulfonamides Incorporating Aminoalcohol, Aminochalcone and Aminostilbene Structural Motifs as Potent Anti-VRE Agents, and Carbonic Anhydrases I, II, VII, IX, and XII Inhibitors

“…All spectral data of known compounds ( 17 , 35 , 37 , 39 , 43 ) are in agreement with those previously reported [ 40 ].…”

“…The synthesis and characterization of some of the presented compounds ( 1 – 3 , 5 – 15 , 17 – 20 , 22 – 24 , 35 , 37 , 39 , 43 ) were previously reported by our group [ 38 , 39 , 40 ]. However, the targeted biological activities discussed in this article were not determined in the previous articles.…”

1,3,5‐Triazine: A versatile pharmacophore with diverse biological activities

“…These compounds were assayed for antioxidant properties by using 1,1-diphenyl-2-picrylhydrazyl radical scavenging assay, 2,2ʹ-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) radical decolorization assay, and metal chelating methods. [106] Havránková et al [107] synthesized a series of 1,3,5-triazine analogs, incorporating aminobenzene sulfonamide, amino alcohol/ phenol, piperazine, chalcone, or stilbene structural motifs, and evaluated them as potential antioxidants.…”

Green synthesis of ferrocenyl chalcones against triple negative breast cancer

“…[5] Chalcone has a common simple scaffold of α, βunsaturated ketone group, which has high exibility that is favorable to act on a variety of drug targets. [6] Therefore, chalcone exhibits many important pharmacological effects, including anti-tumor, [7] antiobesity, [8] anti-in ammatory, [9] anti-oxidation, [10] and anti-bacterial activities. [11] Several chalcones such as metochalcone (choleretic drug), sofalcone (antiulcer and mucoprotective drug) have been approved for clinical use.…”