Synthesis, Spectroscopic Characteristics and Antibacterial Study of Some Novel Sulphonamides

Hajira Rehman; Abdul Qadir; Zulfiqar Ali; Nasir Mahmood; Asmat Zahra; Habib Hussain; Tanzeela Gulab Shahzady

doi:10.14233/ajchem.2016.19316

Issue

Vol. 28 No. 2 (2016): Vol 28 Issue 2

Issue Published : November 3, 2015

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis, Spectroscopic Characteristics and Antibacterial Study of Some Novel Sulphonamides

https://doi.org/10.14233/ajchem.2016.19316

Hajira Rehman

Department of Chemistry, University of Punjab, Lahore, Pakistan

Abdul Qadir

Department of Chemistry, University of Punjab, Lahore, Pakistan

Zulfiqar Ali

Department of Chemistry, University of Engineering and Technology, Lahore, Pakistan

Nasir Mahmood

Department of Allied Health Sciences and Chemical Pathalogy, Department of Human Genetics and Molecular Biology, University of Health Sciences, Lahore, Pakistan

Asmat Zahra

Department of Chemistry, University of Punjab, Lahore, Pakistan

Habib Hussain

Department of Chemistry, University of Engineering and Technology, Lahore, Pakistan

Tanzeela Gulab Shahzady

Department of Chemistry, University of Punjab, Lahore, Pakistan

Corresponding Author(s) : Hajira Rehman

aries_cute8@hotmail.com

Asian Journal of Chemistry, Vol. 28 No. 2 (2016): Vol 28 Issue 2
Article Published : November 3, 2015

Abstract

Main purpose of this study was to produce some novel sulfonamides from already existing antibiotics having-NH₂ group in their structure by their simple and low-cost condensation reactions with p-toulene sulfonyl chloride. All reactions were carried out in aqueous media at controlled pH (8-10) with good yield. Characterization of synthesized compounds were done by using FTIR, ¹H NMR, ESI-MS and elemental analysis. Biological activity was evaluated against medically important Gram-positive and Gram-negative bacterial strains using MIC method after observing optical density value by spectrophotometer at 600 nm. All compounds were active against E. coli with MIC value less than 55 μg/mL, while N-((2S,5R,6R)-2-formyl-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptanes-6-yl)-N-tosylacetamide (1) showed pronounced results having MIC value less than 6 μg/mL for both strains.

Keywords

Sulfonamides p-Toluene sulfonyl chloride Antibiotics

Rehman, H., Qadir, A., Ali, Z., Mahmood, N., Zahra, A., Hussain, H., & Shahzady, T. G. (2015). Synthesis, Spectroscopic Characteristics and Antibacterial Study of Some Novel Sulphonamides. Asian Journal of Chemistry, 28(2), 343–346. https://doi.org/10.14233/ajchem.2016.19316

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References

N. Hen, M. Bialer, B. Wlodarczyk, R.H. Finnell and B. Yagen, J. Med. Chem., 53, 4177 (2010); doi:10.1021/jm100170w.

F. Carta, A. Maresca, A. Scozzafava, D. Vullo and C.T. Supuran, Bioorg. Med. Chem., 17, 7093 (2009); doi:10.1016/j.bmc.2009.09.003.

K. Namba, X. Zheng, K. Motoshima, H. Kobayashi, A. Tai, E. Takahashi, K. Sasaki, K. Okamoto and H. Kakuta, Enterococcus Bioorg. Med. Chem., 16, 6131 (2008); doi:10.1016/j.bmc.2008.04.040.

P. Joseph, F. Turtaut, S. Ouahrani-Bettache, J.L. Montero, I. Nishimori, T. Minakuchi, D. Vullo, A. Scozzafava, S. Kohler, J.-Y. Winum and C.T. Supuran, J. Med. Chem., 53, 2277 (2010); doi:10.1021/jm901855h.

B.G. Katzung, Basic and Clinical Pharmacology, University of California, San Francisco, USA, edn 6 (1995).

S. Joshi and N. Khosla, Bioorg. Med. Chem. Lett., 13, 3747 (2003); doi:10.1016/j.bmcl.2003.08.017.

S. Joshi, N. Khosla and P. Tiwari, Bioorg. Med. Chem., 12, 571 (2004); doi:10.1016/j.bmc.2003.11.001.

N. Anand, in ed. M. E. Wolff, Sulfonamides and Sulfones, In: Burger’s Medicinal Chemistry and Drug Discovery, John Wiley & Sons, Inc., New York, pp. 527-573 (1996).

A. Kamal, M.N.A. Khan, K.S. Reddy, K. Rohini, G.N. Sastry, B. Sateesh and B. Sridhar, Bioorg. Med. Chem. Lett., 17, 5400 (2007); doi:10.1016/j.bmcl.2007.07.043.

S. Zimmerman, A. Innocenti, A. Casini, J.G. Ferry, A. Scozzafava and C.T. Supuran, Bioorg. Med. Chem. Lett., 14, 6001 (2004); doi:10.1016/j.bmcl.2004.09.085.

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L. Puccetti, G. Fasolis, D. Vullo, Z.H. Chohan, A. Scozzafava and C.T. Supuran, Bioorg. Med. Chem. Lett., 15, 3096 (2005); doi:10.1016/j.bmcl.2005.04.055.

J.M. Lehtonen, S. Parkkila, D. Vullo, A. Casini, A. Scozzafava and C.T. Supuran, Bioorg. Med. Chem. Lett., 14, 3757 (2004); doi:10.1016/j.bmcl.2004.04.106.

O. Güzel, A. Innocenti, A. Scozzafava, A. Salman and C.T. Supuran, Bioorg. Med. Chem. Lett., 19, 3170 (2009); doi:10.1016/j.bmcl.2009.04.123.

A. Scozzafava, T. Owa, A. Mastrolorenzo and C.T. Supu-ran, Curr. Med. Chem., 10, 925 (2003); doi:10.2174/0929867033457647.

A. Weber, A. Casini, A. Heine, D. Kuhn, C.T. Supuran, A. Scozzafava and G. Klebe, J. Med. Chem., 47, 550 (2004); doi:10.1021/jm030912m.

G. Sezonov, D. Joseleau-Petit and R. D'Ari, J. Bacteriol., 189, 8746 (2007); doi:10.1128/JB.01368-07.

Issue

Vol. 28 No. 2 (2016): Vol 28 Issue 2

Synthesis, Spectroscopic Characteristics and Antibacterial Study of Some Novel Sulphonamides

Corresponding Author(s) : Hajira Rehman

Abstract

Keywords

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