Synthesis and antibacterial evaluation of 2-(1,3- Benzodioxol-5-ylcarbonyl)arylsulfonohydrazide derivatives

  • A Siddiqa
  • A Rehman
  • MA Abbasi
  • S Rasool
  • KM Khan
  • I Ahmad
  • S Afzal
Keywords: 1, 3-Benzodioxol-5-carboxylic acid, Antibacterial activity, Sulfonohydrazide, Synthesis

Abstract

Purpose: To study the antibacterial activity of various sulfonamides derived from 1,3-benzodioxol-5- carbohydrazide.
Methods: The synthesis involved the conversion of 1,3-benzodioxol-5-carboxylic acid (1) to ethyl 1,3- benzodioxol-5-carboxylate (2) and then to 1,3-benzodioxol-5-carbohydrazide (3). The target molecules, 2-(1,3-benzodioxol-5-ylcarbonyl)arylsulfonohydrazide derivatives (5a-l) were synthesized through a benignant method from aqueous medium by the reaction of 3 and arylsulfonyl chlorides (4a-l). The structural formulae of the synthesized compounds were characterized by infra red spectroscopy (IR), proton nuclear magnetic resonance (1H-NMR) and electron impact mass spectrometry (EI-MS). The compounds were screened for in vitro antibacterial activity by determining their minimum inhibitory concentration (MIC).
Results: The molecule, 5k, bearing 2-hydroxy-3,5-dichlorophenyl group exhibited the highest activity with MIC of 11.92 ± 3.40 (S. typhi), 8.37 ± 2.22 (E. coli), 9.28 ± 2.31 (P. aeroginosa), 11.76 ± 1.30 (B. subtilis) and 10.30 ± 1.63 (S. aureus) μmoles/L relative to that of ciprofloxacin with 9.42 ± 1.09, 8.02 ± 2.17, 8.11 ± 1.32, 8.88 ± 2.00 and 9.23 ± 1.87 μmoles/L respectively.
Conclusion: The most potent of the synthesized compounds (5k) posesses moderate activity against all the bacterial strains, while 5g remained completely inactive.

Keywords: 1,3-Benzodioxol-5-carboxylic acid, Antibacterial activity, Sulfonohydrazide, Synthesis

Published
2014-12-10
Section
Articles

Journal Identifiers


eISSN: 1596-9827
print ISSN: 1596-5996