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Original Research Article
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 and 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:
Email:
azizryk@yahoo.com,
rehman@gcu.edu.pk; Tel:
(+92)-42-111000010 ext 450
Received: 19 December 2013 Revised accepted: 22
August 2014
Tropical
Journal of Pharmaceutical Research, October 2014;
13(10): 1689-1696
http://dx.doi.org/10.4314/tjpr.v13i10.17
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 |
