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A computational study at the density functional theory level was performed on bioactive and model sulfonamides with the aim of determining the factors affecting the acidity of the sulfonamido group. The effects of introducing different substituents at either the para-aryl or the N 1 -sulfonamide positions were independently analyzed. A linear correlation was found between sulfonamide acidity...
Acylation of antimalarial and bacteriostatic sulfonamides with N-protected amino acids and peptides was carried out using standard peptide coupling methods. These acylation reactions are regioselective for the N4 nitrogen atom of diazine-containing sulfonamides. In contrast, only N1 coupling was found for sulfisoxazole, an isoxazole-based sulfonamide. Computational studies suggest that a combination...
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