Tropical Journal of Pharmaceutical Research

Original Research Article | OPEN ACCESS

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

Asia Siddiqa¹, Aziz-ur-Rehman¹ , Muhammad Athar Abbasi¹, Shahid Rasool¹, Khalid Mohammed Khan², Irshad Ahmad³, Saira Afzal³

¹Department of Chemistry, Government College University, Lahore-54000; ²HEJ Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi-75270; ³Department of Pharmacy, The Islamia University of Bahawalpur, Bahawalpur-63100, Pakistan.

For correspondence:- Aziz-ur-Rehman Email: azizryk@yahoo.com Tel:+9242111000010

Received: 19 December 2013 Accepted: 22 August 2014 Published: 19 October 2014

Citation: Siddiqa A, Aziz-ur-Rehman , Abbasi MA, Rasool S, Khan KM, Ahmad I, et al. Synthesis and Antibacterial Evaluation of 2-(1,3-Benzodioxol-5-ylcarbonyl)arylsulfonohydrazide Derivatives. Trop J Pharm Res 2014; 13(10):1689-1696 doi: 10.4314/tjpr.v13i10.17

© 2014 The authors.
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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