Synthesis of 5-amino-1,3,4-thiadiazole-2-sulphonamide derivatives and their inhibition effects on human carbonic anhydrase isozymes

Kasımoğulları, Rahmi; Bülbül, Metín; Mert, Samet; Güleryüz, Hülya

doi:10.3109/14756366.2010.491795

Cited by 13 publications

(12 citation statements)

References 44 publications

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“…Compounds (3) and (4) have good antiproliferative activity against C6 at high concentrations. Also (3) and (4) tested for the inhibition over human cytosolic isozymes (CA I and CA II) in our previous work as in vitro (Kasimogullari et al, 2011). Interestingly, these two compounds showed the greatest effect over CA I and CA II between the tested compounds.…”

Section: Discussionmentioning

confidence: 99%

“…Compound (1) was previously prepared and it was used as a starting compound in this study (Kasimogullari et al, 2011). Also the compounds 4-benzoyl-1-(2-methyl-1-(2-oxopropyl)-1H-indol-5-yl)-5-phenyl-N-(5-sulphamoyl-1,3, 4-thiadiazol-2-yl)-1H-pyrazole-3-carboxamide (2), 4-benzoyl-1-(4-iodophenyl)-5-phenyl-N-(5-sulphamoyl-1,3,4-thiadiazol-2-yl)-1H-pyrazole-3-carboxamide (3), 4-benzoyl -1-(4-((4-hydroxyphenyl)diazenyl)phenyl)-5-phenyl-N-(5-sulphamoyl-1,3,4-thiadiazol -2-yl)-1H-pyrazole-3-carboxamide (4), and 4-benzoyl-1-(4-(2-(1,3-dioxo-1,3-diphenylpropan-2-ylidene)hydrazinyl)phenyl)-5-phenyl-N-(5-sulphamoyl-1,3, 4-thiadiazol-2-yl)-1H-pyrazole-3-carboxamide (6) were synthesized and characterized in our previous work (Kasimogullari et al, 2011).…”

Section: Methodsmentioning

confidence: 99%

“…Pyrazole-sulfonamides (2-9) were characterized by disappearance of a broad singlet at 6.51 ppm due to NH 2 group of (1) (Kasimogullari et al, 2011). The resonances between *7.80 and *6.60 ppm can be assigned to aromatic protons.…”

Section: Chemistrymentioning

confidence: 99%

“…The most remarkable mechanism is the inhibition of carbonic anhydrase isoenzymes (CA) (Abbate et al, 2004;Casini et al, 2002). Previously we studied about synthesis and biological activity of some sulfonamide containing pyrazole-3-carboxamides (Kasimogullari et al, 2011;Sen et al, 2013). We observed many compounds have inhibition potential on human carbonic anhydrase isoenzymes (CA I and CA II).…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and antiproliferative activities of some pyrazole-sulfonamide derivatives

et al. 2013

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In this study, a series of pyrazole-sulfonamide derivatives were designed and synthesized from 1-(4-aminophenyl)-4-benzoyl-5-phenyl-N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)-1H-pyrazole-3-carboxamide (1). The newly synthesized sulfonamides were characterized by FT-IR, 1 H NMR, 13 C NMR, and elemental analyses. The compounds were tested for their in vitro antiproliferative activities against HeLa and C6 cell lines. The tests were carried out as dose-dependent assay starting from 5 to 100 lg/mL. All compounds showed especially cell selective effect against rat brain tumor cells (C6). Some of the tested compounds (3) and (7) showed promising broad spectrum antitumor activity comparable to the activities of the commonly used anticancer drugs, 5-fluorouracil and cisplatin.

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Section: Discussionmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis and antiproliferative activities of some pyrazole-sulfonamide derivatives

et al. 2013

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“…Up to now myriad CA inhibitors have been synthesized or isolated as sulfonamide and non-sulfonamide (such as phenols, thiols, coumarins, polyamines, and dithiocarbamates) inhibitors (Kasımog˘ulları et al, 2011;Go¨cer et al, 2014;Bilginer et al, 2014;Akbaba et al, 2013;Carta et al, 2010Carta et al, , 2012Carta et al, , 2013Almajan et al, 2005;Davis et al, 2013). Therefore, the synthetic studies continue at a great pace today for the synthesis of new CAIs that have a good inhibitory profile with minimal side effects.…”

Section: Introductionmentioning

confidence: 97%

Novel pyrazole-3,4-dicarboxamides bearing biologically active sulfonamide moiety as potential carbonic anhydrase inhibitors

Mert

Alım

İşgör

et al. 2019

Arabian Journal of Chemistry

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In this study a series of pyrazole-3,4-dicarboxamide (3-10) derivatives bearing sulfonamide moiety were synthesized starting from 1-(3-nitrophenyl)-5-phenyl-1H-pyrazole-3,4-dicarboxylic acid (1). The structures of synthesized molecules were characterized by FT-IR, 1 H NMR, 13 C NMR, and elemental analysis methods. Human carbonic anhydrase isoenzymes (hCA I and hCA II) were purified separately from erythrocyte cells by the Sepharose-4B-L-tyrosine-sulfa nilamide affinity column chromatography and inhibitory effects of newly synthesized sulfonamides on esterase activities of these isoenzymes have been studied as in vitro. The K i values of compounds were found in the range of 0.056-110.400 lM for hCA I and 0.057-533.400 lM for hCA II. Compound 4 has the highest inhibitory effect for hCA I and hCA II while compound 5 showed lowest inhibition. The structure-activity relationships for the inhibition of these isoforms with the pyrazole-sulfonamides reported here were also elucidated. ª 2015 The Authors. Production and hosting by Elsevier B.V. on behalf of King Saud University. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).

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Synthesis, molecular docking analysis, drug‐likeness evaluation, and inhibition potency of new pyrazole‐3,4‐dicarboxamides incorporating sulfonamide moiety as carbonic anhydrase inhibitors

Özkul,

Tunca,

Mert

et al. 2024

J Biochem & Molecular Tox

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A series of novel pyrazole‐dicarboxamides were synthesized from pyrazole‐3,4‐dicarboxylic acid chloride and various primary and secondary sulfonamides. The structures of the new compounds were confirmed by FT‐IR, 1H‐NMR, 13C‐NMR, and HRMS. Then the inhibition effects of newly synthesized molecules on human erythrocyte hCA I and hCA II isoenzymes were investigated. Ki values of the compounds were in the range of 0.024−0.496 µM for hCA I and 0.006−5.441 µM for hCA II. Compounds 7a and 7i showed nanomolar level of inhibition of hCA II, and these compounds exhibited high selectivity for this isoenzyme. Molecular docking studies were performed between the most active compounds 7a, 7b, 7i, and the reference inhibitor AAZ and the hCAI and hCAII to investigate the binding mechanisms between the compounds and the isozymes. These compounds showed better interactions than the AAZ. ADMET and drug‐likeness analyses for the compounds have shown that the compounds can be used pharmacologically in living organisms.

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Synthesis of 5-amino-1,3,4-thiadiazole-2-sulphonamide derivatives and their inhibition effects on human carbonic anhydrase isozymes

Cited by 13 publications

References 44 publications

Synthesis and antiproliferative activities of some pyrazole-sulfonamide derivatives

Synthesis and antiproliferative activities of some pyrazole-sulfonamide derivatives

Novel pyrazole-3,4-dicarboxamides bearing biologically active sulfonamide moiety as potential carbonic anhydrase inhibitors

Synthesis, molecular docking analysis, drug‐likeness evaluation, and inhibition potency of new pyrazole‐3,4‐dicarboxamides incorporating sulfonamide moiety as carbonic anhydrase inhibitors

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