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

Spectrochim Acta A Mol Biomol Spectrosc. 2012 Dec;98:329-36. doi: 10.1016/j.saa.2012.08.043. Epub 2012 Sep 1.

Abstract

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, (1)H NMR, (13)C 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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Infective Agents / chemistry*
  • Anti-Infective Agents / pharmacology*
  • Bacteria / drug effects
  • Bacterial Infections / drug therapy
  • Candida albicans / drug effects
  • Candidiasis / drug therapy
  • Escherichia coli / drug effects
  • Humans
  • Hydrazones / chemistry*
  • Hydrazones / pharmacology*
  • Microbial Sensitivity Tests
  • Quantitative Structure-Activity Relationship
  • Staphylococcus aureus / drug effects
  • Sulfonamides / chemistry*
  • Sulfonamides / pharmacology*

Substances

  • Anti-Infective Agents
  • Hydrazones
  • Sulfonamides