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

Eva Havránková,Pavel Pazdera,Jozef Csöllei,Tereza Padrtová,Radka Opatřilová,Nikola Čalkovská

doi:10.3390/molecules25081787

Eva Havránková, Pavel Pazdera + Show 4 more

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https://doi.org/10.3390/molecules25081787

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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.

Highlights

Oxidative stress or damage is the imbalance between the capacity of antioxidative protection systems of the organism and the occurrence of reactive oxygen species and/or reactive nitrogen species [1,2]
Target compounds to the diversityby provides for the design and synthesis new, highly effective methodology published by our
With the increasing number of in the aminobenzene sulfonamide, structural moiety decreases reported by Garaj et al [46]

Summary

Introduction

Oxidative stress or damage is the imbalance between the capacity of antioxidative protection systems of the organism and the occurrence of reactive oxygen species and/or reactive nitrogen species [1,2]. Cytostatics, drugs targeting DNA (e.g., doxorubicin and daunorubicin), highly induce the levels of oxidative stress [10,11,12]. This is one of the reasons why cytostatics possess chemotherapyinduced toxicity and a broad spectra of side effects [11,12,13]. Oxidative stress slows down the progression of the cell cycle, interferes with drug-induced apoptosis, and can diminish the effectiveness of the Molecules 2020, 25, 1787; doi:10.3390/molecules25081787 www.mdpi.com/journal/molecules

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