Synthesis of Biologically Active N-Benzyl-N-[(3,4-methylenedioxyphenyl)methyl]arylsulfonamides

Asia Siddiqa; Aziz-ur Rehman; M. Athar Abbasi; Shahid Rasool; Irshad Ahmad; Saira Afzal

doi:10.14233/ajchem.2014.16156

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.

Synthesis of Biologically Active N-Benzyl-N-[(3,4-methylenedioxyphenyl)methyl]arylsulfonamides

https://doi.org/10.14233/ajchem.2014.16156

Asia Siddiqa

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

Aziz-ur Rehman

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

M. Athar Abbasi

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

Shahid Rasool

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

Irshad Ahmad

Department of Pharmacy; The Islamia University of Bahawalpur, Bahawalpur-63100, Pakistan

Saira Afzal

Department of Pharmacy; The Islamia University of Bahawalpur, Bahawalpur-63100, 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

A new series of N-benzyl-N-[(3,4-methylenedioxyphenyl)methyl]arylsulfonamides (5a-f) was synthesized by using (3,4-methylenedioxyphenyl)methylamine (1). Compound 1 on reaction with arylsulfonyl chlorides (2a-f) in a weak basic aqueous medium gave N-[(3,4-methylenedioxyphenyl)methyl]arylsulfonamides (3a-f), which were converted to target molecules 5a-f, by the reaction of 3a-f with electrophile, benzyl chloride (4) in the presence of LiH and N,N-dimethylformamide. All the synthesized molecules were characterized by IR, ¹H NMR and EIMS. Further, all the molecules were screened for the antibacterial activity and showed moderately good inhibition activity.

Keywords

Antibacterial activity (3,4-Methylenedioxyphenyl)methylamine Arylsulfonyl chlorides

Siddiqa, A., Rehman, A.- ur, Athar Abbasi, M., Rasool, S., Ahmad, I., & Afzal, S. (2014). Synthesis of Biologically Active N-Benzyl-N-[(3,4-methylenedioxyphenyl)methyl]arylsulfonamides. Asian Journal of Chemistry, 26(15), 4651–4654. https://doi.org/10.14233/ajchem.2014.16156

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References

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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. Biol. Res., 2, 100 (2012).
M.A. Abbasi, Aziz-ur-Rehman, T. Muhmood, K. M. Khan, M. Ashraf, S.A. Ejaz and S. Arshad, J. Chem. Soc. Pak., 35, 404 (2013).
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References

A. Behrami and I. Krasniqi, Res. J. Pharm. Biol. Chem. Sci., 3, 369 (2012).

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

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

N. Ozbek, H. Katircioglu, N. Karacan and T. Baykal, Bioorg. Med. Chem., 15, 5105 (2007); doi:10.1016/j.bmc.2007.05.037.

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.

Aziz-ur-Rehman, Awais-ur-Rehman, M.A. Abbasi, H. Khalid, K.M. Khan and P. Dar, Asian J. Pharm. Heath Sci., 2, 384 (2012).

Aziz-ur-Rehman S. Rasool, M.A. Abbasi, A. Fatima, K. Nafeesa, I. Ahmad and S. Afzal, J. Pharm. Res., 6, 559 (2013).

B. Bar-Oz, T. Einarson, A. Einarson, R. Boskovic, L. O’Brien, H. Malm, A. Bérard and G. Koren, Clin. Ther., 29, 918 (2007); doi:10.1016/j.clinthera.2007.05.003.

L. Ingrassia, F. Lefranc, V. Mathieu, F. Darro and R. Kiss, Translational Oncol., 1, 1 (2008); doi:10.1593/tlo.08100.

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. Biol. Res., 2, 100 (2012).

M.A. Abbasi, Aziz-ur-Rehman, T. Muhmood, K. M. Khan, M. Ashraf, S.A. Ejaz and S. Arshad, J. Chem. Soc. Pak., 35, 404 (2013).

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

H.L. Mobley, M.J. Cortesia, L.E. Rosenthal and B.D. Jones, J. Clin. Microbiol., 26, 831 (1988).

Issue

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

Synthesis of Biologically Active N-Benzyl-N-[(3,4-methylenedioxyphenyl)methyl]arylsulfonamides

Corresponding Author(s) : Aziz-ur Rehman

Abstract

Keywords

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