A class of sulfonamides as carbonic anhydrase I and II inhibitors

Abstract

Four groups of novel sulfonamide derivatives: (i) acetoxybenzamide, (ii) triacetoxybenzamide, (iii) hydroxybenzamide and (iv) trihydroxybenzamide, all having thiazole, pyrimidine, pyridine, isoxazole and thiadiazole moieties were prepared and their inhibitory effects were studied on two metalloenzymes, i.e. carbonic anhydrase isozymes (hCA I and II), purified from human erythrocyte cells by Sepharose-4B-l-tyrosine-sulfanilamide affinity chromatography. These enzymes are present in almost all living organisms to catalyse the synthesis of bicarbonate ion (HCO₃⁻) from carbon dioxide and water. The sulfonamide derivatives were found to be active against hCA I and II in the range of 2.62–136.54 and 5.74–210.58 nM, respectively.

Keywords:

• Enzyme inhibition
• gallic acid
• p-hydroxybenzoic acid

Acknowledgements

We thank Prof. Ramazan Altundas of Ataturk University for his useful discussions, F. Melike Al of University of Applied Sciences (BeuthHS) for her support for the synthetic studies, Dr. Meryem Topal for carbonic anhydrase inhibition activity studies, Dr. Ilker Un and Muhiddin Cergel for NMR spectrums and Gokhan Bilsel for HRMS spectrums.

Declaration of interest

The authors have declared no conflict of interest.

Supplementary material available online