Synthesis and evaluation of sulfonamide-bearing thiazole as carbonic anhydrase isoforms hCA I and hCA II

Abstract

Sulfonamide-bearing thiazole compounds were synthesized and their inhibitory effects on the activity of purified human carbonic anhydrase I and II were evaluated. Human carbonic anhydrase isoenzymes (hCA-I and hCA-II) were purified from erythrocyte cells by affinity chromatography. The inhibitory effects of the 12 synthesized sulfonamide (5a-l) on the hydratase and esterase activities of these isoenzymes (hCA-I and hCA-II) were studied in vitro. In relation to these activities, the inhibition equilibrium constants (Ki) were determined. The results showed that all the synthesized compounds inhibited the CA isoenzyme activity. Among them 5b was found to be the most active (IC 50 ¼ 0.35 mM; Ki: 0.33 mM) for hCA I and hCA II.

Sulfonamides incorporating ketene N,S‐acetal bioisosteres as potent carbonic anhydrase and acetylcholinesterase inhibitors

“…Nitrile and amide carbonyl peaks are seen around 2,220 and 1,660–1,700 cm −1 , respectively. As seen in the literature, [ 54 ] there are two peaks assigned to S═O, symmetric and asymmetric stretching, that are observed around 1,330 and 1,150 cm −1 . All spectra and elemental analyses support the structure of the synthesized compounds.…”

New Isoindole‐1,3‐dione Substituted Sulfonamides as Potent Inhibitors of Carbonic Anhydrase and Acetylcholinesterase: Design, Synthesis, and Biological Evaluation

“…In the infrared spectra of compounds 4 a–k , it was possible to observe the absorptions around 3300 cm −1 relating to NH 2 stretchings and absorptions around 1720 cm −1 from carbonyl moiety stretching. As can be seen in the literature, there are two peaks assigned to S=O as symmetric and asymmetric stretching. The peaks of asymmetric and symmetric stretch are appeared around 1350 and 1100 cm −1 , respectively.…”

Synthesis of new series of thiazol‐(2(3H)‐ylideneamino)benzenesulfonamide derivatives as carbonic anhydrase inhibitors

“…The Fourier-transform infrared spectra displayed characteristic absorption bands at around 3260, 3143, 2300, 1650, 1350, and 1110 cm −1 regions, confirming the presence of NH 2 , ═C-H, C═N, C═C, SO 2 , respectively. As can be seen in the literature, [35] Sulfonamides are coordinated to the zinc(II) ion within the hCAs' active site, making intermolecular interactions with amino acid residues both at the bottom, middle, and entrance of the active site cavity. [36] Many CA inhibitors are studied in the literature, for example, sulfonamides, especially primary sulfonamides [37] which are used for antiglaucoma drugs and their isosteres (such as sulfamates, sulfamides, and similar derivatives); polyamines [38] such as spermine, spermidine, and congeners; phenols [39] ; urea/thiourea compounds [40] and β-lactams.…”