Synthesis of 4-(2-substituted hydrazinyl)benzenesulfonamides and their carbonic anhydrase inhibitory effects

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GÜL H. İ., Kucukoglu K., Yamali C., BİLGİNER S., YUCA H., Ozturk I., ...More

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, vol.31, no.4, pp.568-573, 2016 (SCI-Expanded)

• Publication Type: Article / Article
• Volume: 31 Issue: 4
• Publication Date: 2016
• Doi Number: 10.3109/14756366.2015.1047359
• Journal Name: JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY
• Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
• Page Numbers: pp.568-573
• Keywords: 2-Acethylfuran, 2-acethylthiophene, acetophenones, carbonic anhydrase, enzyme inhibition, indanone, sulfonamide, TROUT ONCORHYNCHUS-MYKISS, ERYTHROCYTES IN-VITRO, THERAPEUTIC APPLICATIONS, SULFONAMIDE DERIVATIVES, ENZYME-ACTIVITY, ISOENZYMES I, ISOZYMES I, ISOFORMS I, PURIFICATION, PEROXIDASE
• Çukurova University Affiliated: No

Abstract

In this study, 4-(2-substituted hydrazinyl)benzenesulfonamides were synthesized by microwave irradiation and their chemical structures were confirmed by H-1 NMR, (CNMR)-C-13, and HRMS. Ketones used were: Acetophenone (S1), 4-methylacetophenone (S2), 4-chloroacetophenone (S3), 4-fluoroacetophenone (S4), 4-bromoacetophenone (S5), 4-methoxyacetophenone (S6), 4-nitroacetophenone (S7), 2-acetylthiophene (S8), 2-acetylfuran (S9), 1-indanone (S10), 2-indanone (S11). The compounds S9, S10 and S11 were reported for the first time, while S1-S8 was synthesized by different method than literature reported using microwave irradiation method instead of conventional heating in this study. The inhibitory effects of 4-(2-substituted hydrazinyl) benzenesulfonamide derivatives (S1-S11) against hCA I and II were studied. Cytosolic hCA I and II isoenzymes were potently inhibited by new synthesized sulphonamide derivatives with K-is in the range of 1.79 +/- 0.22-2.73 +/- 0.08 nM against hCA I and in the range of 1.72 +/- 0.58-11.64 +/- 5.21nM against hCA II, respectively.