Abstract
A study was made of correlation of carbonic anhydrase inhibitory activity with the chemical structures of 19 derivatives of benzenesulfonamide and 3 heterocyclic sulfonamides in reference to the physicochemical properties of the compounds. A linear correlation was observed for Hammett's σ factor against pKa, chemical shift of the sulfamoyl protons, and valence-force constant of the S=O bond. Inhibitory activity increased with a decrease of pKa, and with an increase of Hammett's σ factor, chemical shift of the sulfamoyl protons, and the S=O valence-force constant of the sulfamoyl group. A close correlation was also found between the inhibitory activity and water solubility of the unionized molecules of benzenesulfonamides except for p-CH3NH and o-NO2 derivatives.
