Synthesis of N-(Un)Substituted-N-(2-Methoxyphenyl/Phenyl)-4-Chlorobenzenesulfonamides as Potent Antibacterial Derivatives

Aziz-ur- Rehman; M. Athar Abbasi; Sohail Nadeem; Tahir Rasheed; Naeem Ahmed; Misbah Irshad; Kaniz Rubab

doi:10.14233/ajchem.2015.16704

Issue

Vol. 27 No. 1 (2015): Vol 27 Issue 1

Issue Published : December 27, 2014

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

Synthesis of N-(Un)Substituted-N-(2-Methoxyphenyl/Phenyl)-4-Chlorobenzenesulfonamides as Potent Antibacterial Derivatives

https://doi.org/10.14233/ajchem.2015.16704

Aziz-ur- Rehman

Department of Chemistry, Government College University, Lahore-54000, Pakistan

M. Athar Abbasi

Department of Chemistry, Government College University, Lahore-54000, Pakistan

Sohail Nadeem

2Department of Chemistry, School of Science and Technology, University of Management and Technology, Lahore, Pakistan

Tahir Rasheed

Department of Chemistry, Government College University, Lahore-54000, Pakistan

Naeem Ahmed

Department of Chemistry, Government College University, Lahore-54000, Pakistan

Misbah Irshad

Department of Chemistry, Government College University, Lahore-54000, Pakistan

Kaniz Rubab

Department of Chemistry, Government College University, Lahore-54000, Pakistan

Corresponding Author(s) : Aziz-ur- Rehman

azizryk@yahoo.com

Asian Journal of Chemistry, Vol. 27 No. 1 (2015): Vol 27 Issue 1
Article Published : December 26, 2014

Abstract

Sulfonamides belong to a biologically dynamic class of compounds with considerable importance for organic synthetic chemists. In the presented work, a benign series of chlorinated sulfonamides, 3a-b, was synthesized by coupling alkoxy (un) substituted anilines, 2a-b, with 4-chlorobenzenesulfonyl chloride (1) under basic pH control in an aqueous medium. The sulfonamides, 3a-b, were geared up with alkyl/aralkyl halides, 4-6, in a basic aprotic solvent to yield the target molecules, 7a-b, 8a-b and 9a-b. The structures of all the derivatives were furnished by ¹H NMR, IR and EI-MS spectral analysis. All the synthesized compounds were screened for a-chemotrypsin and antibacterial activities.

Keywords

Substituted anilines 4-Chlorobenzenesulfonyl chloride Enzyme inhibition study

Rehman, A.- ur-., Abbasi, M. A., Nadeem, S., Rasheed, T., Ahmed, N., Irshad, M., & Rubab, K. (2014). Synthesis of N-(Un)Substituted-N-(2-Methoxyphenyl/Phenyl)-4-Chlorobenzenesulfonamides as Potent Antibacterial Derivatives. Asian Journal of Chemistry, 27(1), 71–74. https://doi.org/10.14233/ajchem.2015.16704

Download Citation

References

Aziz-ur-Rehman, S. Rasool, M.A. Abbasi, A. Fatima, K. Nafeesa, I. Ahmad and S. Afzal, J. Pharm. Res., 6, 559 (2013); doi:10.1016/j.jopr.2013.05.003.
A. Alsughayer, A.Z.A. Elassar, S. Mustafa and F. Al-Sagheer, J. Biomater. Nanobiotechnol., 2, 143 (2011); doi:10.4236/jbnb.2011.22018.
S. Kumar, M.S. Niranjan, K.C. Chaluvaraju, C.M. Jamakhandi and D. Kadadevar, J. Curr. Pharm. Res., 1, 39 (2010).
J.M. Baskin and Z. Wang, Tetrahedron Lett., 43, 8479 (2002); doi:10.1016/S0040-4039(02)02073-7.
A. Thakur, M. Thakur and P.V. Khadikar, ARKIVOC, 87 (2006); doi:10.3998/ark.5550190.0007.e12.
F. Shi, M.K. Tse, S. Zhou, M.-M. Pohl, J. Radnik, S. Hübner, K. Jähnisch, A. Brückner and M. Beller, J. Am. Chem. Soc., 131, 1775 (2009); doi:10.1021/ja807681v.
S.M. Sondhi, A.D. Dwivedi, J. Singh and P.P. Gupta, Indian J. Chem., 49B, 1076 (2010).
G.E. Cami, R.D. Arellano, M.C. Del, S. Fustero and J.C. Pedregosa, J. Argentine Chem. Soc., 94, 5 (2006).
I. Argyropoulou, A. Geronikaki, P. Vicini and F. Zani, ARKIVOC, 89 (2008); doi:10.3998/ark.5550190.0010.611.
H. Khalid, Aziz-ur-Rehman, M.A. Abbasi, A. Malik, S. Rasool, K. Nafeesa, I. Ahmad and S. Afzal, J. Saudi Chem. Soc., doi:10.1016/j.jscs.2013.05.001.
H. Khalid, Aziz-ur-Rehman, M.A. Abbasi and K.M. Khan, Int. J. Pharm. Pharm. Sci., 4, 443 (2012).
Aziz-ur-Rehman, S. Rasool, M.A. Abbasi, K.M. Khan, M. Asraf and I. Afzal, Asian J. Pharm. Bio. Res., 2, 100 (2012).
13 N.M. Tariq, S.U. Wisam, H.M. Faik and T.H. Mayson, Pak. J. Chem., 3, 1 (2013); doi:10.15228/2013.v03.i01.p01.
Aziz-ur-Rehman, A. Fatima, M.A. Abbasi, S. Rasool, A. Malik, M. Ashraf, I. Ahmad and S.A. Ejaz, J. Saudi Chem. Soc., doi:10.1016/j.jscs.2013.02.006.
Aziz-ur-Rehman, S. Tahir, M.A. Abbasi, S. Rasool, A. Siddiqa, Awais-ur-Rehman, A. Muhammad and A. Sharif, Asian J. Chem., 25, 9000 (2013); doi:10.14233/ajchem.2013.14964.
16 M.R.H. Siddiqui, J. Chem., Article ID 780939 (2013); doi:10.1155/2013/780939.
M.A. Abbasi, M.A. Lodhi, V.U. Ahmad and M.I. Choudhary, J. Asian Nat. Prod. Res., 11, 933 (2009); doi:10.1080/10286020903321539.

References

Aziz-ur-Rehman, S. Rasool, M.A. Abbasi, A. Fatima, K. Nafeesa, I. Ahmad and S. Afzal, J. Pharm. Res., 6, 559 (2013); doi:10.1016/j.jopr.2013.05.003.

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

S. Kumar, M.S. Niranjan, K.C. Chaluvaraju, C.M. Jamakhandi and D. Kadadevar, J. Curr. Pharm. Res., 1, 39 (2010).

J.M. Baskin and Z. Wang, Tetrahedron Lett., 43, 8479 (2002); doi:10.1016/S0040-4039(02)02073-7.

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

F. Shi, M.K. Tse, S. Zhou, M.-M. Pohl, J. Radnik, S. Hübner, K. Jähnisch, A. Brückner and M. Beller, J. Am. Chem. Soc., 131, 1775 (2009); doi:10.1021/ja807681v.

S.M. Sondhi, A.D. Dwivedi, J. Singh and P.P. Gupta, Indian J. Chem., 49B, 1076 (2010).

G.E. Cami, R.D. Arellano, M.C. Del, S. Fustero and J.C. Pedregosa, J. Argentine Chem. Soc., 94, 5 (2006).

I. Argyropoulou, A. Geronikaki, P. Vicini and F. Zani, ARKIVOC, 89 (2008); doi:10.3998/ark.5550190.0010.611.

H. Khalid, Aziz-ur-Rehman, M.A. Abbasi, A. Malik, S. Rasool, K. Nafeesa, I. Ahmad and S. Afzal, J. Saudi Chem. Soc., doi:10.1016/j.jscs.2013.05.001.

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

Aziz-ur-Rehman, S. Rasool, M.A. Abbasi, K.M. Khan, M. Asraf and I. Afzal, Asian J. Pharm. Bio. Res., 2, 100 (2012).

13 N.M. Tariq, S.U. Wisam, H.M. Faik and T.H. Mayson, Pak. J. Chem., 3, 1 (2013); doi:10.15228/2013.v03.i01.p01.

Aziz-ur-Rehman, A. Fatima, M.A. Abbasi, S. Rasool, A. Malik, M. Ashraf, I. Ahmad and S.A. Ejaz, J. Saudi Chem. Soc., doi:10.1016/j.jscs.2013.02.006.

Aziz-ur-Rehman, S. Tahir, M.A. Abbasi, S. Rasool, A. Siddiqa, Awais-ur-Rehman, A. Muhammad and A. Sharif, Asian J. Chem., 25, 9000 (2013); doi:10.14233/ajchem.2013.14964.

16 M.R.H. Siddiqui, J. Chem., Article ID 780939 (2013); doi:10.1155/2013/780939.

M.A. Abbasi, M.A. Lodhi, V.U. Ahmad and M.I. Choudhary, J. Asian Nat. Prod. Res., 11, 933 (2009); doi:10.1080/10286020903321539.

Issue

Vol. 27 No. 1 (2015): Vol 27 Issue 1

Synthesis of N-(Un)Substituted-N-(2-Methoxyphenyl/Phenyl)-4-Chlorobenzenesulfonamides as Potent Antibacterial Derivatives

Corresponding Author(s) : Aziz-ur- Rehman

Abstract

Keywords

Full Article

Download Citation

References

Table Of Contents