Designing,synthesis and bioactivities of 4-[3-(4-hydroxyphenyl)-5-aryl-4,5-dihydro-pyrazol-1-yl]benzenesulfonamides |
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| Authors: | Halise Inci Gul Ebru Mete Sakip Emre Eren Hiroshi Sakagami Cem Yamali Claudiu T Supuran |
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| Institution: | 1. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Ataturk University, Erzurum, Turkey;2. Department of Chemistry, Faculty of Arts and Sciences, Ataturk University, Erzurum, Turkey;3. Division of Pharmacology, Meikai University School of Dentistry, Sakado, Saitama, Japan;4. Polo Scientifico, Laboratorio di Chimica Bioinorganica, Universita degli Studi di Firenze, Sesto Fiorentino, Italy |
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| 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 by 1H 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. |
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| Keywords: | Benzenesulfonamide carbonic anhydrase cytotoxicity phenol pyrazoline |
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