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

J 2020

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

HAVRÁNKOVÁ, Eva, Nikola ČALKOVSKÁ, Tereza PADRTOVÁ, Jozef CSÖLLEI, Radka OPATŘILOVÁ et. al.

Basic information

Original name

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

Authors

HAVRÁNKOVÁ, Eva (203 Czech Republic, belonging to the institution), Nikola ČALKOVSKÁ (203 Czech Republic, belonging to the institution), Tereza PADRTOVÁ (203 Czech Republic, belonging to the institution), Jozef CSÖLLEI (203 Czech Republic, belonging to the institution), Radka OPATŘILOVÁ (203 Czech Republic, belonging to the institution) and Pavel PAZDERA (203 Czech Republic, guarantor, belonging to the institution)

Edition

Molecules, Basel, MDPI, 2020, 1420-3049

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10608 Biochemistry and molecular biology

Country of publisher

Switzerland

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 4.411

RIV identification code

RIV/00216224:14310/20:00115547

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.3390/molecules25081787

UT WoS

000534617300018

Keywords in English

s-triazine; 4-aminophenol; hydroxychalcone; hydroxystilbene; antioxidative activity; ABTS method

Abstract

V originále

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 muM) were 5 times lower for compounds 5, 6, 13, and 25 than EC50 of both standards (trolox = 178.33 muM; ASA = 147.47 muM). 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.

Citovat

HAVRÁNKOVÁ, Eva, Nikola ČALKOVSKÁ, Tereza PADRTOVÁ, Jozef CSÖLLEI, Radka OPATŘILOVÁ and Pavel PAZDERA. Antioxidative Activity of 1,3,5-Triazine Analogues Incorporating Aminobenzene Sulfonamide, Aminoalcohol/Phenol, Piperazine, Chalcone, or Stilbene Motifs. Molecules. Basel: MDPI, 2020, vol. 25, No 8, p. 1-15. ISSN 1420-3049. Available from: https://dx.doi.org/10.3390/molecules25081787.

@article{1646780,
   author = {Havránková, Eva and Čalkovská, Nikola and Padrtová, Tereza and Csöllei, Jozef and Opatřilová, Radka and Pazdera, Pavel},
   article_location = {Basel},
   article_number = {8},
   doi = {http://dx.doi.org/10.3390/molecules25081787},
   keywords = {s-triazine; 4-aminophenol; hydroxychalcone; hydroxystilbene; antioxidative activity; ABTS method},
   language = {eng},
   issn = {1420-3049},
   journal = {Molecules},
   title = {Antioxidative Activity of 1,3,5-Triazine Analogues Incorporating Aminobenzene Sulfonamide, Aminoalcohol/Phenol, Piperazine, Chalcone, or Stilbene Motifs},
   url = {https://doi.org/10.3390/molecules25081787},
   volume = {25},
   year = {2020}
}

TY  - JOUR
ID  - 1646780
AU  - Havránková, Eva - Čalkovská, Nikola - Padrtová, Tereza - Csöllei, Jozef - Opatřilová, Radka - Pazdera, Pavel
PY  - 2020
TI  - Antioxidative Activity of 1,3,5-Triazine Analogues Incorporating Aminobenzene Sulfonamide, Aminoalcohol/Phenol, Piperazine, Chalcone, or Stilbene Motifs
JF  - Molecules
VL  - 25
IS  - 8
SP  - 1-15
EP  - 1-15
PB  - MDPI
SN  - 14203049
KW  - s-triazine
KW  - 4-aminophenol
KW  - hydroxychalcone
KW  - hydroxystilbene
KW  - antioxidative activity
KW  - ABTS method
UR  - https://doi.org/10.3390/molecules25081787
L2  - https://doi.org/10.3390/molecules25081787
N2  - 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 muM) were 5 times lower for compounds 5, 6, 13, and 25 than EC50 of both standards (trolox = 178.33 muM; ASA = 147.47 muM). 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.
ER  -

HAVRÁNKOVÁ, Eva, Nikola ČALKOVSKÁ, Tereza PADRTOVÁ, Jozef CSÖLLEI, Radka OPATŘILOVÁ and Pavel PAZDERA. Antioxidative Activity of 1,3,5-Triazine Analogues Incorporating Aminobenzene Sulfonamide, Aminoalcohol/Phenol, Piperazine, Chalcone, or Stilbene Motifs. \textit{Molecules}. Basel: MDPI, 2020, vol.~25, No~8, p.~1-15. ISSN~1420-3049. Available from: https://dx.doi.org/10.3390/molecules25081787.

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