Microwave-assisted synthesis and bioevaluation of new sulfonamides

Abstract

In this study, 4-[5-(4-hydroxyphenyl)-3-aryl-4,5-dihydro-1H-pyrazol-1-yl]benzenesulfonamide derivatives (8-14) were synthesized for the first time by microwave irradiation and their chemical structures were confirmed by 1H NMR, 13C NMR and HRMS. Cytotoxic activities and inhibitory effects on carbonic anhydrase I and II isoenzymes of the compounds were investigated. The compounds 9 (PSE = 4.2), 12 (PSE = 4.1) and 13 (PSE = 3.9) with the highest potency selectivity expression (PSE) values in cytotoxicity experiments and the compounds 13 (Ki = 3.73 ± 0.91 nM toward hCA I) and 14 (Ki = 3.85 ± 0.57 nM toward hCA II) with the lowest Ki values in CA inhibition studies can be considered as leader compounds for further studies.

Novel N‐propylphthalimide‐ and 4‐vinylbenzyl‐substituted benzimidazole salts: Synthesis, characterization, and determination of their metal chelating effects and inhibition profiles against acetylcholinesterase and carbonic anhydrase enzymes

“…For designation of the inhibition effects of novel synthesised compounds (1, 2a–e, 3, and 4a–f) , both CA isoforms (hCA I and II) were purified and obtained by sepharose‐4B‐ l ‐tyrosine‐sulfanilamide affinity chromatography in a single purification stage. The protein amounts in the column eluates were spectrophotometrically measured at 280 nm . For designation of both isoforms purity, sodium dodecyl sulfate polyacrylamide gel electrophoresis (SDS‐PAGE) was performed after a purification stage.…”

Inhibitory effects of some drugs on carbonic anhydrase enzyme purified from Kangal Akkaraman sheep in Sivas, Turkey

“…CAIs were used in multitude clinical utilizations of main diseases such as antiepileptic, antiobesity drugs, diuretics, gastroduodenal ulcers, antiglaucoma, and acid–base disequilibria. CAIs are beneficial for the treatment of some neurological disturbances such as idiopathic intracranial hypertension …”

Synthesis, molecular modeling, and biological evaluation of 4‐[5‐aryl‐3‐(thiophen‐2‐yl)‐4,5‐dihydro‐1H‐pyrazol‐1‐yl] benzenesulfonamides toward acetylcholinesterase, carbonic anhydrase I and II enzymes

“…First, chalcones were synthesized via Claisen–Schmidt reaction as described in literatures . 2‐Acetylthiophene (2 g, 16 mmol) and the appropriate aromatic aldehyde (1.7 g for 1 , 2.0 g for 2 , 2.2 g for 3 , 2.0 g for 4 , 2.2 g for 5 , 3.0 g for 6 , 2.8 g for 7 , 1.8 g for 8 , 2.6 g for 9 , 2.6 g for 10, 16 mmol) were dissolved in ethanol (10 ml), and an aqueous solution of potassium hydroxide (10 ml, 40% w/v) was added dropwise into the reaction flask.…”

“…At the second step, a solution of the appropriate chalcone (0.5 g, 2 mmol) in ethanol (30 ml) with glacial acetic acid (0.1 ml) was heated until chalcone dissolved and then p ‐hydrazinobenzene sulfonamide hydrochloride (0.5 g, 2 mmol) was added into the reaction mixture, and finally, the mixture was refluxed for 22 hr . The reactions were monitored by TLC plates using chloroform:methanol (5 ml:2 drops) as solvent system.…”