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

Abstract

In this study, 4-(2-substituted hydrazinyl)benzenesulfonamides were synthesized by microwave irradiation and their chemical structures were confirmed by ¹H NMR, ¹³CNMR, 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 ± 5.21 nM against hCA II, respectively.

• 2-Acethylfuran
• 2-acethylthiophene
• acetophenones
• carbonic anhydrase
• enzyme inhibition
• indanone
• sulfonamide

Declaration of interest

The authors report no conflict of interest and are responsible for the contents and writing of the paper.

The authors Gul and Gulcin thank the Ataturk University Research Fund (Project number 2012/75 and 2012/74) and Research Chairs Program at King Saud University for their financial supports. Also, Gulcin would like to extend his sincere appreciation to the Research Chairs Program at King Saud University for funding this research.