Designing, synthesis and bioactivities of 4-[3-(4-hydroxyphenyl)-5-aryl-4,5-dihydro-pyrazol-1-yl] benzenesulfonamides

作者：Gul Halise Inci^*; Mete Ebru; Eren Sakip Emre; Sakagami Hiroshi; Yamali Cem; Supuran Claudiu T

来源：Journal of Enzyme Inhibition and Medicinal Chemistry, 2017, 32(1): 169-175.

DOI：10.1080/14756366.2016.1243536

• Benzenesulfonamide
• carbonic anhydrase
• cytotoxicity
• phenol
• pyrazoline

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 H-1 NMR, C-13 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)-4,5dihydro- 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 53.5-923nM 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.

• 出版日期2017