Potent Antibacterial Agents: N-Substituted Derivatives of N-(4-Methylpyridin-2-yl)benzenesulfonamide

Aziz-ur Rehman; Muhammad Arfan; M. Athar Abbasi; Majid Nazir; Shahid Rasool; Samreen Gul; Irshad Ahmad; Saira Afzal

doi:10.14233/ajchem.2014.16161

Issue

Vol. 26 No. 15 (2014): Vol 26 Issue 15

Issue Published : July 16, 2014

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

Potent Antibacterial Agents: N-Substituted Derivatives of N-(4-Methylpyridin-2-yl)benzenesulfonamide

https://doi.org/10.14233/ajchem.2014.16161

Aziz-ur Rehman

Department of Chemistry, Government College University, Lahore, Pakistan

Muhammad Arfan

Department of Chemistry, Government College University, Lahore, Pakistan

M. Athar Abbasi

Department of Chemistry, Government College University, Lahore, Pakistan

Majid Nazir

Department of Chemistry, Minhaj University, Lahore, Pakistan

Shahid Rasool

Department of Chemistry, Government College University, Lahore, Pakistan

Samreen Gul

Department of Chemistry, Government College University, Lahore, Pakistan

Irshad Ahmad

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; rehman@gcu.edu.pk

Asian Journal of Chemistry, Vol. 26 No. 15 (2014): Vol 26 Issue 15
Article Published : July 16, 2014

Abstract

In the present work, a new series of N-substituted-N-(4-methylpyridin-2-yl)benzenesulfonamides (5a-f), was synthesized and evaluated for antibacterial activity. The synthesis was carried out by the coupling of 2-amino-4-methylpyridine (1) with benzenesulfonyl chloride (2) yielded N-(4-methylpyridin-2-yl)benzenesulfonamide (3) under dynamic pH control of basic aqueous medium of sodium carbonate. Further, the molecule 3 was reacted with different alkyl/aralkyl halides, 4a-f, yielded the products 5a-f, in the presence of N,N-dimethyl formamide and LiH. The proposed structures of synthesized molecules were corroborated by IR, ¹H NMR and EI-MS spectral data and also screened for antibacterial activity. All the compounds exhibited moderately good inhibitors and only compound 5e executed no activity against P. aeroginosa, gram-negative bacterial strain.

Keywords

2-Amino-4-methylpyridine Antibacterial activity Sulfonamide 1H NMR and EI-MS

Rehman, A.- ur, Arfan, M., Athar Abbasi, M., Nazir, M., Rasool, S., Gul, S., … Afzal, S. (2014). Potent Antibacterial Agents: N-Substituted Derivatives of N-(4-Methylpyridin-2-yl)benzenesulfonamide. Asian Journal of Chemistry, 26(15), 4661–4664. https://doi.org/10.14233/ajchem.2014.16161

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References

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A. Camargo-Ordoñez, C. Moreno-Reyes, F. Olazarán-Santibáñez, S. Martínez-Hernández, V. Bocanegra-García and G. Rivera, Quim. Nova, 34, 787 (2011); doi:10.1590/S0100-40422011000500011.

A. Ali, G.S.K.K. Reddy, H. Cao, S.G. Anjum, M.N.L. Nalam, C.A. Schiffer and T.M. Rana, J. Med. Chem., 49, 7342 (2006); doi:10.1021/jm060666p.

A.J. McCarroll, T.D. Bradshaw, A.D. Westwell, C.S. Matthews and M.F.G. Stevens, J. Med. Chem., 50, 1707 (2007); doi:10.1021/jm061163m.

B.L. Wilkinson, L.F. Bornaghi, T.A. Houston, A. Innocenti, D. Vullo, C.T. Supuran and S.-A. Poulsen, J. Med. Chem., 50, 1651 (2007); doi:10.1021/jm061320h.

J. Drews, Science, 287, 1960 (2000); doi:10.1126/science.287.5460.1960.

A.E. Boyd, Diabetes, 37, 847 (1988); doi:10.2337/diab.37.7.847.

C.T. Supuran and A. Scozzafava, Expert Opin. Ther. Patents, 10, 575 (2000); doi:10.1517/13543776.10.5.575.

A.A. Kadi, N.R. El-Brollosy, O.A. Al-Deeb, E.E. Habib, T.M. Ibrahim and A.A. El-Emam, Eur. J. Med. Chem., 42, 235 (2007); doi:10.1016/j.ejmech.2006.10.003.

S. Schenone, C. Brullo, O. Bruno, F. Bondavalli, A. Ranise, W. Filippelli, B. Rinaldi, A. Capuano and G. Falcone, Bioorg. Med. Chem., 14, 1698 (2006); doi:10.1016/j.bmc.2005.10.064.

M.M. Ghorab, F.A. Ragab, H.I. Heiba and R.M. El-Hazek, Eur. J. Med. Chem., 46, 5120 (2011); doi:10.1016/j.ejmech.2011.08.026.

J.P. Liou, K.S. Hsu, C.C. Kuo, C.Y. Chang and J.Y. Chang, J. Pharmacol. Exp. Ther., 323, 398 (2007); doi:10.1124/jpet.107.126680.

(a) S.W. Wright and K.N. Hallstrom, J. Org. Chem., 71, 1080 (2006); doi:10.1021/jo052164+.; (b) A.R. Katritzky, A.A.A. Abdel-Fattah, A.V. Vakulenko and H. Tao, J. Org. Chem., 70, 9191 (2005); doi:10.1021/jo051157i.

X. Deng and N.S. Mani, Green Chem., 8, 835 (2006); doi:10.1039/b606127c.

M. Jafarpour, A. Rezaeifard and T. Golshani, J. Phosphorous Sulfur Silicon Rel. Elem., 186, 140 (2010); doi:10.1080/10426507.2010.488257.

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.

H. Khalid, Aziz-ur-Rehman, M.A. Abbasi and K.M. Khan, 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 Chemother., 50, 1710 (2006); doi:10.1128/AAC.50.5.1710-1714.2006.

Issue

Vol. 26 No. 15 (2014): Vol 26 Issue 15

Potent Antibacterial Agents: N-Substituted Derivatives of N-(4-Methylpyridin-2-yl)benzenesulfonamide

Corresponding Author(s) : Aziz-ur Rehman

Abstract

Keywords

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