Synthesis and Antibacterial Activity of N-Substituted Derivatives of N-(Oxolan-2-ylmethyl)-4-Chlorobenzenesulfonamide

Aziz -ur-Rehman; Nasir Bashir; M. Athar Abbasi; Shahid Rasool; Ghulam Hussain; Irshad Ahmed; Saira Afzal

doi:10.14233/ajchem.2015.17166

Issue

Vol. 27 No. 4 (2015): Vol 27 Issue 4

Issue Published : February 4, 2015

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

Synthesis and Antibacterial Activity of N-Substituted Derivatives of N-(Oxolan-2-ylmethyl)-4-Chlorobenzenesulfonamide

https://doi.org/10.14233/ajchem.2015.17166

Aziz -ur-Rehman

Department of Chemistry, Government College University, Lahore, Pakistan

Nasir Bashir

Department of Chemistry, Government College University, Lahore, Pakistan

M. Athar Abbasi

Department of Chemistry, Government College University, Lahore, Pakistan

Shahid Rasool

Department of Chemistry, Government College University, Lahore, Pakistan

Ghulam Hussain

Department of Chemistry, Government College University, Lahore, Pakistan

Irshad Ahmed

Department of Pharmacy, The Islamia University of Bahawalpur, Bahawalpur, Pakistan

Saira Afzal

Department of Pharmacy, The Islamia University of Bahawalpur, Bahawalpur, Pakistan

Corresponding Author(s) : Aziz -ur-Rehman

azizryk@yahoo.com

Asian Journal of Chemistry, Vol. 27 No. 4 (2015): Vol 27 Issue 4
Article Published : February 3, 2015

Abstract

A series of new N-substituted derivatives of N-(oxolan-2-ylmethyl)-4-chlorobenzenesulfonamide (3) have been synthesized and further evaluated for antibacterial activity. The molecule N-(oxolan-2-ylmethyl)-4-chlorobenzenesulfonamide (3), was prepared in an aqueous basic medium by the reaction of 2-oxolanemethylamine (1) and 4-chlorobenzenesulfonyl chloride (2) under dynamic pH control. It was further stepped up to yield N-alkyl/aralkyl-N-(oxolan-2-ylmethyl)-4-chlorobenzenesulfonamides (5a-f) by its reaction with alkyl/aralkyl halides (4a-f) in a polar aprotic medium in the presence of lithium hydride. The proposed structures of the synthesized molecules were corroborated by IR, ¹H NMR and EI-MS spectral data. The resulted MIC values of these compounds showed their good activity against S. aureus, the Gram-positive bacteria.

Keywords

2-Oxolanemethylamine 4-Chlorobenzenesulfonyl chloride Antibacterial activity Sulfonamides

-ur-Rehman, A., Bashir, N., Athar Abbasi, M., Rasool, S., Hussain, G., Ahmed, I., & Afzal, S. (2015). Synthesis and Antibacterial Activity of N-Substituted Derivatives of N-(Oxolan-2-ylmethyl)-4-Chlorobenzenesulfonamide. Asian Journal of Chemistry, 27(4), 1205–1208. https://doi.org/10.14233/ajchem.2015.17166

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References

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References

C.T. Supuran, A. Casini and A. Scozzafava, Med. Res. Rev., 23, 535 (2003); doi:10.1002/med.10047.

A.R. Long, L.C. Hsieh, M.S. Malbrough, C.R. Short and S.A. Barker, J. Agric. Food Chem., 38, 423 (1990); doi:10.1021/jf00092a018.

M.J. García-Galán, M. Silvia Díaz-Cruz and D. Barceló, Trends Analyt. Chem., 27, 1008 (2008); doi:10.1016/j.trac.2008.10.001.

A. Khazaei, S.F. Sadeghian, S. Hesami and A.A. Manesh, Asian J. Chem., 14, 173 (2002).

G.L. Perlovich, N.N. Strakhova, V.P. Kazachenko, T.V. Volkova, V.V. Tkachev, K.-J. Schaper and O.A. Raevsky, Int. J. Pharm., 349, 300 (2008); doi:10.1016/j.ijpharm.2007.07.034.

A.K. Gadad, C.S. Mahajanshetti, S. Nimbalkars and A. Raichurkar, Eur. J. Med. Chem., 35, 853 (2000); doi:10.1016/S0223-5234(00)00166-5.

M.J. García-Galán, M. Silvia Díaz-Cruz and D. Barceló, Trends Analyt. Chem., 27, 1008 (2008); doi:10.1016/j.trac.2008.10.001.

A. Thakur, M. Thakur and P.V. Khadikar, ARKIVOC, 87 (2006); doi:10.3998/ark.5550190.0007.e12.

A. Alsughayer, A.Z.A. Elassar, S. Mustafa and F. Al-Sagheer, J. Biomater. Nanobiotechnol., 2, 143 (2011); doi:10.4236/jbnb.2011.22018.

W.Y. Chan and C. Berthelette, Tetrahedron Lett., 43, 4537 (2002); doi:10.1016/S0040-4039(02)00848-1.

A. Boruah, M. Baruah, D. Prajapati and J.S. Sandhu, Synlett, 1253 (1997); doi:10.1055/s-1997-1015.

W. Yuan, K. Fearon and M.H. Gelb, J. Org. Chem., 54, 906 (1989); doi:10.1021/jo00265a034.

H. Khalid, Aziz-ur-Rehman, M.A. Abbasi and K.M. Khan, Int. J. Pharm. Pharm. Sci., 4, 443 (2012).

Aziz-ur-Rehman, S. Afroz, M.A. Abbasi, W. Tanveer, K.M. Khan, M. Ashraf, I. Afzal and N. Ambreen, Pak. J. Pharm. Sci., 25, 809 (2012).

M. Kaspady, V.K. Narayanaswamy, M. Raju and G.K. Rao, Lett. Drug Des. Discov., 6, 21 (2009); doi:10.2174/157018009787158481.

C.-R. Yang, Y. Zhang, M.R. Jacob, S.I. Khan, Y.-J. Zhang and X.-C. Li, Antimicrob. Agents Chemoth., 50, 1710 (2006); doi:10.1128/AAC.50.5.1710-1714.2006.

Issue

Vol. 27 No. 4 (2015): Vol 27 Issue 4

Synthesis and Antibacterial Activity of N-Substituted Derivatives of N-(Oxolan-2-ylmethyl)-4-Chlorobenzenesulfonamide

Corresponding Author(s) : Aziz -ur-Rehman

Abstract

Keywords

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