Novel sulfonamide incorporating piperazine, aminoalcohol and 1,3,5-triazine structural motifs with carbonic anhydrase I, II and IX inhibitory action

Havránková, Eva; Csöllei, Jozef; Vullo, Daniela; Garaj, Vladimír; Pazdera, Pavel; Supuran, Claudiu T.

doi:10.1016/j.bioorg.2017.12.034

Cited by 30 publications

(46 citation statements)

References 37 publications

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“…All spectral data of known compounds (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14) agreed with those previously reported [48].…”

Section: General Informationsupporting

confidence: 87%

“…To summarize, tested compounds were demonstrated as valuable potential as antioxidants useful in the treatment of diseases caused by oxidative stress. Besides, the antioxidant effect is a great benefit for compounds that are excellent inhibitors of hCA IX (compound 5) [48] since oxidative stress is associated with tumor development and progression in several malignancies. In addition, the antioxidative properties may have a beneficial effect in suppressing the side effects associated with the treatment using some classic cytostatic drugs [11,49].…”

Section: Antioxidant Evaluationmentioning

confidence: 99%

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

et al. 2020

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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.

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“…All spectral data of known compounds (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14) agreed with those previously reported [48].…”

Section: General Informationsupporting

confidence: 87%

Section: Antioxidant Evaluationmentioning

confidence: 99%

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

et al. 2020

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“…Tested compounds showed great potential as antioxidants useful in the treatment of diseases caused by oxidative stress. Besides, the antioxidant effect is a great benefit for compounds that are excellent inhibitors of hCA IX (compound 1) [16] since oxidative stress is associated with tumor development and progression in several tumors. Also, the antioxidative properties may have a beneficial effect in suppressing the side effects associated with the treatment using some classic cytostatics [17,18].…”

Section: Resultsmentioning

confidence: 99%

“…Compounds previously reported in[16]; 2 Errors in the range of 1-5% of the reported value (Mean from three different assays).…”

mentioning

confidence: 99%

New 1,3,5-Triazine Derivatives Incorporating Aminobenzenesulfonamide, Aminoalcohol, Piperazine, Chalcone or Stilbene Structural Motifs and Evaluation of Their Antioxidative Activity

Havránková

Čalkovská

Padrtova

et al. 2019

The 23rd International Electronic Conference on Synthetic Organic Chemistry

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A series of 1,3,5-triazine derivatives, incorporating aminobenzenesulfonamide, 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 IC50, using the ABTS method. Trolox and ascorbic acid (ASA) were used as standards. In the lowest used concentration 1 × 10 −4 M, the %inhibition activity at time 0 min was comparable with both standards at least for 10 compounds. After 60 min compounds 1, 2, 9 and 25 showed nearly twice %inhibition (73.44-87.09%) in comparison with standards (Trolox = 41.49%; ASA = 31.07%). Values of IC50 correlated with %inhibition activity . For compounds 1, 2, 9 and 25 values of IC50 in time 60 min (17.16-27.78 μM) were 5 times lower than IC50 of both standards (Trolox = 178.33 μM; ASA = 147.47 μM). Based on these results, the presented 1,3,5-triazine derivatives and their analogs have a high potential in the treatment of illnesses caused or related to oxidative stress.

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“…Sulphonamides are considered as one of famous drug categories which utilized for treatment of several diseases according to their functional uses as antihypertensive agent, antiprotozoal, anti‐inflammatory, antibacterial, antifungal . Many of valuable sulphonamide drugs that inhibit carbonic anhydrase . Up till now, sulphonamide still the treatment choice for neurogenic blocking agents, while nerve blockade is used as a complementary to diuretics‐sulphonamide when optimal control of hypertension is not obtained with these drugs alone .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Docking Study of Pyrimidine Derivatives Scaffold for Anti‐Hypertension Application

Katouah

Gaffer

2019

ChemistrySelect

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The present work introduces four new macromolecules pyrrolo[2,3‐d]pyrimidine scaffolds substituted with various benzene‐sulfonamide moieties; those were picked up via cyclization of 2‐amino‐3‐cyanopyrroles with phenyl isothiocyanate. The newly prepared pyrrolopyrimidine derivatives have been elucidated by spectroscopic techniques (FT‐IR, 1HNMR, 13CNMR and MS) and elemental analyses. The antihypertensive activity of the synthesized pyrrolopyrimidine derivatives based on sulfonamide moiety was evaluated. All pyrrolopyrimidine derivatives were showed a potent antihypertensive activity than Prazosin that utilized as standard drug. The structure activity relationship (SAR) was studied to correlate the influence of sulfonamide group with the aminopyrimidine moiety. Molecular docking for the synthesized derivatives and theoretical statistics were carried out to expect their antihypertensive efficacy.

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Novel sulfonamide incorporating piperazine, aminoalcohol and 1,3,5-triazine structural motifs with carbonic anhydrase I, II and IX inhibitory action

Cited by 30 publications

References 37 publications

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

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

New 1,3,5-Triazine Derivatives Incorporating Aminobenzenesulfonamide, Aminoalcohol, Piperazine, Chalcone or Stilbene Structural Motifs and Evaluation of Their Antioxidative Activity

Synthesis and Docking Study of Pyrimidine Derivatives Scaffold for Anti‐Hypertension Application

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