Antioxidative Activity of 1,3,5-Triazine Analogues Incorporating Aminobenzene Sulfonamide, Aminoalcohol/Phenol, Piperazine, Chalcone, or Stilbene Motifs
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...
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MDPI AG
2020-04-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/25/8/1787 |
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| author | Eva Havránková Nikola Čalkovská Tereza Padrtová Jozef Csöllei Radka Opatřilová Pavel Pazdera |
| author_facet | Eva Havránková Nikola Čalkovská Tereza Padrtová Jozef Csöllei Radka Opatřilová Pavel Pazdera |
| author_sort | Eva Havránková |
| collection | DOAJ |
| description | 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 EC<sub>50</sub>, using the ABTS method. Trolox and ascorbic acid (ASA) were used as standards. In the lowest concentration 1 × 10<sup>−4</sup> M, the %inhibition activity values at 0 min were comparable with both standards at least for 10 compounds. After 60 min, compounds <b>5</b>, <b>6</b>, <b>13</b>, and <b>25</b> showed nearly twice %inhibition (73.44–87.09%) in comparison with the standards (Trolox = 41.49%; ASA = 31.07%). Values of EC<sub>50</sub> at 60 min (17.16–27.78 μM) were 5 times lower for compounds <b>5</b>, <b>6</b>, <b>13</b>, and <b>25</b> than EC<sub>50</sub> of both standards (trolox = 178.33 μM; ASA = 147.47 μM). Values of EC<sub>50</sub> 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. |
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| last_indexed | 2024-03-10T20:29:21Z |
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| spelling | doaj.art-c764328cea0a4b9689ac75b2b3ca9ed32023-11-19T21:33:24ZengMDPI AGMolecules1420-30492020-04-01258178710.3390/molecules25081787Antioxidative Activity of 1,3,5-Triazine Analogues Incorporating Aminobenzene Sulfonamide, Aminoalcohol/Phenol, Piperazine, Chalcone, or Stilbene MotifsEva Havránková0Nikola Čalkovská1Tereza Padrtová2Jozef Csöllei3Radka Opatřilová4Pavel Pazdera5Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, 612 42 Brno, Czech RepublicDepartment of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, 612 42 Brno, Czech RepublicDepartment of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, 612 42 Brno, Czech RepublicDepartment of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, 612 42 Brno, Czech RepublicDepartment of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, 612 42 Brno, Czech RepublicDepartment of Chemistry, Faculty of Science, Centre for Syntheses at Sustainable Conditions and Their Management, Masaryk University, 625 00 Brno, Czech RepublicA 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 EC<sub>50</sub>, using the ABTS method. Trolox and ascorbic acid (ASA) were used as standards. In the lowest concentration 1 × 10<sup>−4</sup> M, the %inhibition activity values at 0 min were comparable with both standards at least for 10 compounds. After 60 min, compounds <b>5</b>, <b>6</b>, <b>13</b>, and <b>25</b> showed nearly twice %inhibition (73.44–87.09%) in comparison with the standards (Trolox = 41.49%; ASA = 31.07%). Values of EC<sub>50</sub> at 60 min (17.16–27.78 μM) were 5 times lower for compounds <b>5</b>, <b>6</b>, <b>13</b>, and <b>25</b> than EC<sub>50</sub> of both standards (trolox = 178.33 μM; ASA = 147.47 μM). Values of EC<sub>50</sub> 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.https://www.mdpi.com/1420-3049/25/8/17871,3,5-triazine4-aminophenolhydroxychalconehydroxystilbeneantioxidative activityABTS method |
| spellingShingle | Eva Havránková Nikola Čalkovská Tereza Padrtová Jozef Csöllei Radka Opatřilová Pavel Pazdera Antioxidative Activity of 1,3,5-Triazine Analogues Incorporating Aminobenzene Sulfonamide, Aminoalcohol/Phenol, Piperazine, Chalcone, or Stilbene Motifs Molecules 1,3,5-triazine 4-aminophenol hydroxychalcone hydroxystilbene antioxidative activity ABTS method |
| title | Antioxidative Activity of 1,3,5-Triazine Analogues Incorporating Aminobenzene Sulfonamide, Aminoalcohol/Phenol, Piperazine, Chalcone, or Stilbene Motifs |
| title_full | Antioxidative Activity of 1,3,5-Triazine Analogues Incorporating Aminobenzene Sulfonamide, Aminoalcohol/Phenol, Piperazine, Chalcone, or Stilbene Motifs |
| title_fullStr | Antioxidative Activity of 1,3,5-Triazine Analogues Incorporating Aminobenzene Sulfonamide, Aminoalcohol/Phenol, Piperazine, Chalcone, or Stilbene Motifs |
| title_full_unstemmed | Antioxidative Activity of 1,3,5-Triazine Analogues Incorporating Aminobenzene Sulfonamide, Aminoalcohol/Phenol, Piperazine, Chalcone, or Stilbene Motifs |
| title_short | Antioxidative Activity of 1,3,5-Triazine Analogues Incorporating Aminobenzene Sulfonamide, Aminoalcohol/Phenol, Piperazine, Chalcone, or Stilbene Motifs |
| title_sort | antioxidative activity of 1 3 5 triazine analogues incorporating aminobenzene sulfonamide aminoalcohol phenol piperazine chalcone or stilbene motifs |
| topic | 1,3,5-triazine 4-aminophenol hydroxychalcone hydroxystilbene antioxidative activity ABTS method |
| url | https://www.mdpi.com/1420-3049/25/8/1787 |
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