title: Designing, synthesis and bioactivities of 4-[3-(4-hydroxyphenyl)-5-aryl-4,5-dihydro-pyrazol-1-yl]benzenesulfonamides.
abstract: In this study, 4-[3-(4-hydroxyphenyl)-5-aryl-4,5-dihydro-pyrazol-1-yl]benzenesulfonamide (1-9) types compounds were synthesized and their chemical structures were confirmed by1H NMR,13C NMR and HRMS spectra. Cytotoxic and carbonic anhydrase (CA) inhibitory effects of the compounds were investigated. Cytotoxicity experiments pointed out that compound 4, (4-[5-(4-chlorophenyl)-3-(4-hydroxyphenyl)-4,5-dihydro-pyrazol-1-yl]benzenesulfonamide), exerting the highest tumor selectivity (TS) and potency selectivity expression (PSE) values, can be considered as a lead compound of this study in terms of development of novel anticancer agents. All synthesized sulfonamides showed a good inhibition profile on hCA IX and XII in the range of 53.5-923 nM and 6.2-95 nM, respectively. These compounds were 2.5-13.4 times more selective for the inhibition of hCA XII versus hCA IX, except compound 2 which had similar inhibitory action towards both isoenzymes.
authors: a Department of Pharmaceutical Chemistry, Faculty of Pharmacy , Ataturk University , Erzurum , Turkey.
authors: Halise Inci
authors: HI
authors: Gul
authors: b Department of Chemistry, Faculty of Arts and Sciences , Ataturk University , Erzurum , Turkey.
authors: Ebru
authors: E
authors: Mete
authors: a Department of Pharmaceutical Chemistry, Faculty of Pharmacy , Ataturk University , Erzurum , Turkey.
authors: Sakip Emre
authors: SE
authors: Eren
authors: c Division of Pharmacology , Meikai University School of Dentistry , Sakado, Saitama , Japan.
authors: Hiroshi
authors: H
authors: Sakagami
authors: a Department of Pharmaceutical Chemistry, Faculty of Pharmacy , Ataturk University , Erzurum , Turkey.
authors: Cem
authors: C
authors: Yamali
authors: d Polo Scientifico , Laboratorio di Chimica Bioinorganica, Universita degli Studi di Firenze , Sesto Fiorentino , Italy.
authors: Claudiu T
authors: CT
authors: Supuran
mesh_terms: D066244:Proton Magnetic Resonance Spectroscopy; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000096926:Benzenesulfonamides
chemical_list: D013449:Sulfonamides; D000096926:Benzenesulfonamides
keywords: Benzenesulfonamide; carbonic anhydrase; cytotoxicity; phenol; pyrazoline