Synthesis, Characterization and Biological Activities of 2-[(Methyl sulfonyl)]amino Benzoic Acid Derivatives and Their Metal Complexes

Tanveer Hussain Bokhari; Naveeda Ashraf; Muhammad Shafiq; Matloob Ahmed; Nasir Rasool; Hazoor Ahmad Shad; Nabeela Ashraf; Nadeem Arshad; Muhammad Nawaz Tahir

doi:10.14233/ajchem.2015.17807

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, Characterization and Biological Activities of 2-[(Methyl sulfonyl)]amino Benzoic Acid Derivatives and Their Metal Complexes

https://doi.org/10.14233/ajchem.2015.17807

Tanveer Hussain Bokhari

Department of Chemistry, Government College University, Faisalabad-38000, Pakistan

Naveeda Ashraf

Department of Chemistry, Government College University, Faisalabad-38000, Pakistan

Muhammad Shafiq

Department of Chemistry, Government College University, Faisalabad-38000, Pakistan

Matloob Ahmed

Department of Chemistry, Government College University, Faisalabad-38000, Pakistan

Nasir Rasool

Department of Chemistry, Government College University, Faisalabad-38000, Pakistan

Hazoor Ahmad Shad

Department of Chemistry, University of Sargodha-60800, Pakistan

Nabeela Ashraf

Department of Applied Chemistry, UET, Lahore-54890, Pakistan

Nadeem Arshad

Center of Excellence for Advanced Materials Research (CEAMR), Faculty of Science, King Abdulaziz University, Kingdom of Saudi Arabia

Muhammad Nawaz Tahir

Department of Physics, University of Sargodha-60800, Pakistan

Corresponding Author(s) : Tanveer Hussain Bokhari

tanveer.bokhari@yahoo.com

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

Abstract

Sulfonamide derivatives and their metal complexes are acknowledged pharmaceutical moieties because this group has been played the key role as a functional part of the most of the drug structures due to constancy and for bearance in human beings. Sulfonamides have endowed great biological potential such as antibacterial, insulin releasing, carbonic anhydrase inhibitory, anti-inflammatory, antifungal and antitumor activities. In the present work, 2-[(methyl sulfonyl)] amino benzoic acid was N-alkylated using alkylating agent such as methyl. Due to the presence of electron donating groups like, -COOH, -SO₂, N-, the above mentioned molecules act as an excellent chelating agent. These substituted N-alkylated sulfonamide ligands were treated with a number of outer and inner transition metals such as Co(II), Cu(II), Ce(II), Pr(II), Dy(II) and Nd(II) to form coordinate complexes. These newly synthesized sulfonamides and their metal complexes were characterized by melting points, solubility, colour, FTIR analysis and XRD. These products were subjected for antimicrobial activities as well as other accessible applications.

Keywords

Sulfonamide derivatives Pharmaceutical agent Antibacterial Antifungal

Hussain Bokhari, T., Ashraf, N., Shafiq, M., Ahmed, M., Rasool, N., Ahmad Shad, H., … Nawaz Tahir, M. (2015). Synthesis, Characterization and Biological Activities of 2-[(Methyl sulfonyl)]amino Benzoic Acid Derivatives and Their Metal Complexes. Asian Journal of Chemistry, 27(4), 1326–1330. https://doi.org/10.14233/ajchem.2015.17807

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References

Z.A. Siddiqi, M. Khalid, S. Kumar, M. Shahid and S. Noor, Eur. J. Med. Chem., 45, 264 (2010); doi:10.1016/j.ejmech.2009.10.005.
G.F. Yang and H. Z. Yang, Chin. J. Chem., 17, 650 (1999).
B.R. Stranix, J.-F. Lavallée, G. Sévigny, J. Yelle, V. Perron, N. LeBerre, D. Herbart and J.J. Wu, Bioorg. Med. Chem. Lett, 16, 3459 (2004); doi:10.1016/j.bmcl.2006.04.011.
S. Cezar and K. Angela, Acta Chim. Slov., 47, 179 (2000).
P. Selvam, D.F. Smee, B.B. Gowen, C.W. Day, D. Barnard and J. Morrey, Antiviral Res., 74, 81 (2007); doi:10.1016/j.antiviral.2007.01.139.
H.S. Patel and H.J. Mistry, Phosphorous, Sulfur, Silicon Rel. Elem., 179, 1085 (2004); doi:10.1080/10426500490459704.
C.T. Supuran, A. Casini, A. Mastrolorenzo and A. Scozzafava, Mini Rev. Med. Chem., 4, 625 (2004); doi:10.2174/1389557043403792.
T.H. Maren, Annu. Rev. Pharmacol. Toxicol., 16, 309 (1976); doi:10.1146/annurev.pa.16.040176.001521.
J.J. Li, D. Anderson, E.G. Burton, J.N. Cogburn, J.T. Collins, D.J. Garland, S.A. Gregory, H.C. Huang, P.C. Isakson, C.M. Koboldt, E.W. Logusch, M.B. Norton, W.E. Perkins, E.J. Reinhard, K. Seibert, A.W. Veenhuizem, Y. Zang and D.B. Reitz, J. Med. Chem., 38, 4570 (1995); doi:10.1021/jm00022a023.
A.K. Gadad, C.S. Mahajanshetti, S. Nimbalkar and A. Raichurkar, Eur. J. Med. Chem., 35, 853 (2000); doi:10.1016/S0223-5234(00)00166-5.
V.S. Misra, V.K. Saxena and R. Srivastava, J. Indian Chem. Soc., 59, 781 (1982).
F. Zani and P. Vicini, Arch. Pharm., 331, 219 (1998); doi:10.1002/(SICI)1521-4184(199806)331:6<219::AID-ARDP219>3.0.CO;2-U.
C.T. Supuran, A. Scozzafava, B.C. Jurca and M.A. Ilies, Eur. J. Med. Chem., 33, 83 (1998); doi:10.1016/S0223-5234(98)80033-0.
G. Renzi, A. Scozzafava and C.T. Supuran, Bioorg. Med. Chem. Lett., 10, 673 (2000); doi:10.1016/S0960-894X(00)00075-5.
H. Yoshino, N. Ueda, J. Niijima, H. Sugumi, Y. Kotake, N. Koyanagi, K. Yoshimatsu, M. Asada and T. Watanabe, J. Med. Chem., 35, 2496 (1992); doi:10.1021/jm00091a018.
D.J. Abraham, W.S. John and N.J. Hoboken, Burger's Medicinal Chemistry and Drug Discovery, John Wiley & Sons, New Jersey (2003).
E.D. Clercq Curr. Med. Chem., 8, 1543 (2001); doi:10.2174/0929867013371842.
C. Wu, E.R. Decker, G.W. Holland, F.D. Brown, F.D. Stavros, T.A. Brock and R.A.C. Dixon, Drugs Today, 37, 441 (2001); doi:10.1358/dot.2001.37.7.844187.
J.K. Barton, J.M. Goldberg, C.V. Kumar and N.J. Turro, J. Am. Chem. Soc., 108, 2081 (1986); doi:10.1021/ja00268a057.
S. Delaney, M. Pascaly, P.K. Bhattacharya, K. Han and J.K. Barton, Inorg. Chem., 41, 1966 (2002); doi:10.1021/ic0111738.
A.P. Mishra and S.K. Gavtarm, J. Indian Chem. Soc., 81, 324 (2004).
N.A. Venkariya, M.D. Khunt and A.P. Parikh, Indian J. Chem., 42B, 421 (2003).
N.M. Sivasankaran and S.T. David, J. Indian Chem. Soc., 77, 220 (2000).
R.K. Murray and D.K. Granner, Haper Biochemistry, Appleton and Lange, Stamford (1996).
N. Raman, S. Ravichandran and C. Thangaraja, J. Chem. Sci., 116, 215 (2004); doi:10.1007/BF02708270.
J.G. Lombardino, J. Chem., 9, 315 (1971).
M. Shafiq, M. Zia-ur-rehman, I.U. Khan, M.N. Arshad and I. Ahmad, Acta Crystal.,E65, o2453 (2009);doi:10.1107/S1600536809036113.
C. Tang, R. Tang, C. Tang and Z. Zeng, Bull. Korean Chem. Soc., 31, 1283 (2010); doi:10.5012/bkcs.2010.31.5.1283.
K. Nakamoto, IR and Raman Spectra of Inorganic and Coordination Complexes, Part A: Theory and Applications in Inorganic Chemistry, edn 5, Wiley, New York (1997).
M. Thomas, M.K.M. Nair and P.K. Radhakrishnan, Synth. React. Inorg. Met-Org. Chem., 25, 471 (1995); doi:10.1080/15533179508218235.
M.M. Ali, M.M.F. Ismail, M.S.A. El-Gaby, M.A. Zahran and Y.A. Ammar, Molecules, 5, 864 (2000); doi:10.3390/50600864.
K. Jamil, M. Bakhtiar, A. Khan, F. Rubina, R. Rehana, R. Wajid and M. Qaisar, African J. Pure Appl. Chem., 3, 71 (2009).
M.A. Neelakantan, M. Esakkiammal, S.S. Mariappan, J. Dharmaraja and T. Jeyakumar, Indian J. Pharm. Sci., 72, 216 (2010); doi:10.4103/0250-474X.65015.

References

Z.A. Siddiqi, M. Khalid, S. Kumar, M. Shahid and S. Noor, Eur. J. Med. Chem., 45, 264 (2010); doi:10.1016/j.ejmech.2009.10.005.

G.F. Yang and H. Z. Yang, Chin. J. Chem., 17, 650 (1999).

B.R. Stranix, J.-F. Lavallée, G. Sévigny, J. Yelle, V. Perron, N. LeBerre, D. Herbart and J.J. Wu, Bioorg. Med. Chem. Lett, 16, 3459 (2004); doi:10.1016/j.bmcl.2006.04.011.

S. Cezar and K. Angela, Acta Chim. Slov., 47, 179 (2000).

P. Selvam, D.F. Smee, B.B. Gowen, C.W. Day, D. Barnard and J. Morrey, Antiviral Res., 74, 81 (2007); doi:10.1016/j.antiviral.2007.01.139.

H.S. Patel and H.J. Mistry, Phosphorous, Sulfur, Silicon Rel. Elem., 179, 1085 (2004); doi:10.1080/10426500490459704.

C.T. Supuran, A. Casini, A. Mastrolorenzo and A. Scozzafava, Mini Rev. Med. Chem., 4, 625 (2004); doi:10.2174/1389557043403792.

T.H. Maren, Annu. Rev. Pharmacol. Toxicol., 16, 309 (1976); doi:10.1146/annurev.pa.16.040176.001521.

J.J. Li, D. Anderson, E.G. Burton, J.N. Cogburn, J.T. Collins, D.J. Garland, S.A. Gregory, H.C. Huang, P.C. Isakson, C.M. Koboldt, E.W. Logusch, M.B. Norton, W.E. Perkins, E.J. Reinhard, K. Seibert, A.W. Veenhuizem, Y. Zang and D.B. Reitz, J. Med. Chem., 38, 4570 (1995); doi:10.1021/jm00022a023.

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

V.S. Misra, V.K. Saxena and R. Srivastava, J. Indian Chem. Soc., 59, 781 (1982).

F. Zani and P. Vicini, Arch. Pharm., 331, 219 (1998); doi:10.1002/(SICI)1521-4184(199806)331:6<219::AID-ARDP219>3.0.CO;2-U.

C.T. Supuran, A. Scozzafava, B.C. Jurca and M.A. Ilies, Eur. J. Med. Chem., 33, 83 (1998); doi:10.1016/S0223-5234(98)80033-0.

G. Renzi, A. Scozzafava and C.T. Supuran, Bioorg. Med. Chem. Lett., 10, 673 (2000); doi:10.1016/S0960-894X(00)00075-5.

H. Yoshino, N. Ueda, J. Niijima, H. Sugumi, Y. Kotake, N. Koyanagi, K. Yoshimatsu, M. Asada and T. Watanabe, J. Med. Chem., 35, 2496 (1992); doi:10.1021/jm00091a018.

D.J. Abraham, W.S. John and N.J. Hoboken, Burger's Medicinal Chemistry and Drug Discovery, John Wiley & Sons, New Jersey (2003).

E.D. Clercq Curr. Med. Chem., 8, 1543 (2001); doi:10.2174/0929867013371842.

C. Wu, E.R. Decker, G.W. Holland, F.D. Brown, F.D. Stavros, T.A. Brock and R.A.C. Dixon, Drugs Today, 37, 441 (2001); doi:10.1358/dot.2001.37.7.844187.

J.K. Barton, J.M. Goldberg, C.V. Kumar and N.J. Turro, J. Am. Chem. Soc., 108, 2081 (1986); doi:10.1021/ja00268a057.

S. Delaney, M. Pascaly, P.K. Bhattacharya, K. Han and J.K. Barton, Inorg. Chem., 41, 1966 (2002); doi:10.1021/ic0111738.

A.P. Mishra and S.K. Gavtarm, J. Indian Chem. Soc., 81, 324 (2004).

N.A. Venkariya, M.D. Khunt and A.P. Parikh, Indian J. Chem., 42B, 421 (2003).

N.M. Sivasankaran and S.T. David, J. Indian Chem. Soc., 77, 220 (2000).

R.K. Murray and D.K. Granner, Haper Biochemistry, Appleton and Lange, Stamford (1996).

N. Raman, S. Ravichandran and C. Thangaraja, J. Chem. Sci., 116, 215 (2004); doi:10.1007/BF02708270.

J.G. Lombardino, J. Chem., 9, 315 (1971).

M. Shafiq, M. Zia-ur-rehman, I.U. Khan, M.N. Arshad and I. Ahmad, Acta Crystal.,E65, o2453 (2009);doi:10.1107/S1600536809036113.

C. Tang, R. Tang, C. Tang and Z. Zeng, Bull. Korean Chem. Soc., 31, 1283 (2010); doi:10.5012/bkcs.2010.31.5.1283.

K. Nakamoto, IR and Raman Spectra of Inorganic and Coordination Complexes, Part A: Theory and Applications in Inorganic Chemistry, edn 5, Wiley, New York (1997).

M. Thomas, M.K.M. Nair and P.K. Radhakrishnan, Synth. React. Inorg. Met-Org. Chem., 25, 471 (1995); doi:10.1080/15533179508218235.

M.M. Ali, M.M.F. Ismail, M.S.A. El-Gaby, M.A. Zahran and Y.A. Ammar, Molecules, 5, 864 (2000); doi:10.3390/50600864.

K. Jamil, M. Bakhtiar, A. Khan, F. Rubina, R. Rehana, R. Wajid and M. Qaisar, African J. Pure Appl. Chem., 3, 71 (2009).

M.A. Neelakantan, M. Esakkiammal, S.S. Mariappan, J. Dharmaraja and T. Jeyakumar, Indian J. Pharm. Sci., 72, 216 (2010); doi:10.4103/0250-474X.65015.

Issue

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

Synthesis, Characterization and Biological Activities of 2-[(Methyl sulfonyl)]amino Benzoic Acid Derivatives and Their Metal Complexes

Corresponding Author(s) : Tanveer Hussain Bokhari

Abstract

Keywords

Full Article

Download Citation

References

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