Synthesis and Antibacterial Evaluation of 2-(1,3-Benzodioxol-5-ylcarbonyl)arylsulfonohydrazide Derivatives

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 1,3benzodioxol- 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 (H-1-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) mu moles/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 mu moles/L respectively. Conclusion: The most potent of the synthesized compounds (5k) posesses moderate activity against all the bacterial strains, while 5g remained completely inactive.