title: Synthesis, characterization and in vitro inhibition of metal complexes of pyrazole based sulfonamide on human erythrocyte carbonic anhydrase isozymes I and II.
abstract: Sulfonamides represent an important class of biologically active compounds. A sulfonamide possessing carbonic anhydrase (CA) inhibitory properties obtained from a pyrazole based sulfonamide, ethyl 1-(3-nitrophenyl)-5-phenyl-3-((5-sulfamoyl-1,3,4-thiadiazol-2-yl)carbamoyl)-1H-pyrazole-4-carboxylate (1), and its metal complexes with the Ni(II) for (2), Cu(II) for (3) and Zn(II) for (4) have been synthesized. The structures of metal complexes (2-4) were established on the basis of their elemental analysis,1H NMR, IR, UV-Vis and MS spectral data. The inhibition of two human carbonic anhydrase (hCA, EC 4.2.1.1) isoenzymes I and II, with 1 and synthesized complexes (2-4) and acetazolamide (AAZ) as a control compound was investigated in vitro by using the hydratase and esterase assays. The complexes 2, 3 and 4 showed inhibition constant in the range 0.1460-0.3930 µM for hCA-I and 0.0740-0.0980 µM for hCA-II, and they had effective more inhibitory activity on hCA-I and hCA-II than corresponding free ligand 1 and than AAZ.
authors.affiliation: a Department of Chemistry , Arts and Science Faculty, Dumlupinar University , Kutahya , Turkey.
authors.forename: Nurgün
authors.initials: N
authors.lastname: Büyükkıdan
authors.affiliation: a Department of Chemistry , Arts and Science Faculty, Dumlupinar University , Kutahya , Turkey.
authors.forename: Bülent
authors.initials: B
authors.lastname: Büyükkıdan
authors.affiliation: a Department of Chemistry , Arts and Science Faculty, Dumlupinar University , Kutahya , Turkey.
authors.forename: Metin
authors.initials: M
authors.lastname: Bülbül
authors.affiliation: a Department of Chemistry , Arts and Science Faculty, Dumlupinar University , Kutahya , Turkey.
authors.forename: Rahmi
authors.initials: R
authors.lastname: Kasımoğulları
authors.affiliation: a Department of Chemistry , Arts and Science Faculty, Dumlupinar University , Kutahya , Turkey.
authors.forename: Samet
authors.initials: S
authors.lastname: Mert
mesh_terms: D024401:Carbonic Anhydrase I / Q000037:antagonists & inhibitors* / Q000302:isolation & purification / Q000378:metabolism; D024402:Carbonic Anhydrase II / Q000037:antagonists & inhibitors* / Q000302:isolation & purification / Q000378:metabolism; D002257:Carbonic Anhydrase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D004912:Erythrocytes / Q000187:drug effects* / Q000201:enzymology*; D006801:Humans; D007527:Isoenzymes / Q000037:antagonists & inhibitors / Q000302:isolation & purification / Q000378:metabolism; D019216:Metals, Heavy / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D011720:Pyrazoles / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D013449:Sulfonamides / Q000737:chemistry / Q000494:pharmacology
chemical_list: D002257:Carbonic Anhydrase Inhibitors; D007527:Isoenzymes; D019216:Metals, Heavy; D009942:Organometallic Compounds; D011720:Pyrazoles; D013449:Sulfonamides; D024401:Carbonic Anhydrase I; D024402:Carbonic Anhydrase II
keywords: Carbonic anhydrase; hydratase and esterase activities; metal complexes; pyrazole; sulfonamide