Synthesis of novel sulfonamides under mild conditions with effective inhibitory activity against the carbonic anhydrase isoforms I and II.

Abstract

Novel sulfonamide derivatives 6a-i, as new carbonic anhydrase inhibitors which candidate for glaucoma treatment, were synthesized from the reactions of 4-amino-N-(4-sulfamoylphenyl) benzamide 4 and sulfonyl chloride derivatives 5a-i with high yield (71-90%). The structures of these compounds were confirmed by using spectral analysis (FT-IR, (1)H NMR, (13)C NMR, LC/MS and HRMS). The inhibition effects of 6a-i on the hydratase and esterase activities of human carbonic anhydrase isoenzymes, hCA I and II, which were purified from human erythrocytes with Sepharose®4B-l-tyrosine-p-aminobenzene sulfonamide affinity chromatography, were studied as in vitro, and IC50 and Ki values were determined. The results show that newly synthesized compounds have quite powerful inhibitory properties.

• Authors: Erhan Başar, Ekrem Tunca, Metin Bülbül, Muharrem Kaya
• Journal: Journal of enzyme inhibition and medicinal chemistry (J Enzyme Inhib Med Chem) Vol. 31 Issue 6 Pg. 1356-61 (Dec 2016) ISSN: 1475-6374 [Electronic] England
• PMID: 27541741 (Publication Type: Journal Article)

Chemical References

• Carbonic Anhydrase Inhibitors
• Sulfonamides
• Carbonic Anhydrase I
• Carbonic Anhydrase II

Topics

• Carbonic Anhydrase I (antagonists & inhibitors)
• Carbonic Anhydrase II (antagonists & inhibitors)
• Carbonic Anhydrase Inhibitors (chemical synthesis, pharmacology)
• Erythrocytes (enzymology)
• Humans
• Inhibitory Concentration 50
• Spectrum Analysis (methods)
• Sulfonamides (chemical synthesis, pharmacology)