The antibacterial activity of some sulfonamides and sulfonyl hydrazones, and 2D-QSAR study of a series of sulfonyl hydrazones

Benzenesulfonicacid-1-methylhydrazide (1) and its four aromatic sulfonyl hydrazone derivatives (1a–1d), N-(3-amino-2-hydroxypropyl)benzene sulfonamide (2) and N-(2-hydroxyethyl)benzenesulfonamide (3) were synthesized and their structures were determined by IR, 1H NMR, 13C NMR, and LCMS techniques. Antibacterial activities of new synthesized compounds were evaluated against various bacteria strains by microdilution and disk diffusion methods. The experimental results show that presence of OH group on sulfonamides reduces the antimicrobial activity, and antimicrobial activities of the sulfonyl hydrazones (1a–1d) are smaller than that of the parent sulfonamide (1), except Candida albicans. In addition, 2D-QSAR analysis was performed on 28 aromatic sulfonyl hydrazones as antimicrobial agents against Escherichia coli and Staphylococcus aureus. In the QSAR models, the most important descriptor is total point-charge component of the molecular dipole for E. coli, and partial negative surface area (PNSA-1) for S. aureus.

Graphical abstractPlot of experimental versus predicted pMIC values of training sets of Escherichia coli and Staphylococcus aureus.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► New original sulfonamide and sulfonyl hydrazones were synthesized. ► New compounds were screened for their antibacterial activity. ► 2D-QSAR analysis was performed on aromatic sulfonyl hydrazones used as antimicrobial agents against Escherichia coli and Staphylococcus aureus.