Synthesis, spectral analysis and biological evaluation of Nalkyl/aralkyl/aryl-4-chlorobenzenesulfonamide derivatives

Pak J Pharm Sci. 2016 Sep;29(5):1489-1496.

Abstract

New potent organic compounds were synthesized with an aim of good biological activities such as antibacterial and anti-enzymatic. Three series of sulfonamide derivatives were synthesized by treating N-alkyl/aryl substituted amines (2a-f) with 4-chlorobenzensulfonyl chloride (1) to yield N-alkyl/aryl-4-chlorobenzenesulfonamide(3af) that was then derivatized by gearing up with ethyl iodide (4), benzyl chloride (5) and 4-chlorobenzyl chloride (6) using sodium hydride as base to initialize the reaction in a polar aprotic solvent (DMF) to synthesize the derivatives, 7a-f, 8af and 9a-f respectively. Structure elucidation was brought about by IR, 1H-NMR and EIMS spectra for all the synthesized molecules which were evaluated for their antibacterial activities and inhibitory potentials for certain enzymes.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / pharmacology*
  • Bacteria / drug effects*
  • Bacteria / growth & development
  • Chymotrypsin / antagonists & inhibitors
  • Drug Design*
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / pharmacology*
  • Lipoxygenase Inhibitors / chemical synthesis
  • Lipoxygenase Inhibitors / pharmacology
  • Mass Spectrometry
  • Molecular Structure
  • Proton Magnetic Resonance Spectroscopy
  • Serine Proteinase Inhibitors / chemical synthesis
  • Serine Proteinase Inhibitors / pharmacology
  • Spectrophotometry, Infrared
  • Structure-Activity Relationship
  • Sulfonamides / chemical synthesis*
  • Sulfonamides / pharmacology*

Substances

  • Anti-Bacterial Agents
  • Enzyme Inhibitors
  • Lipoxygenase Inhibitors
  • Serine Proteinase Inhibitors
  • Sulfonamides
  • 4-chlorobenzenesulfonamide
  • Chymotrypsin
  • alpha-chymotrypsin