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Synthesis, Spectral and Biological Studies of Novel Schiff Base Metal Complexes Derived from Cephalexin and Sugars
Corresponding Author(s) : Narjis Naz
Asian Journal of Chemistry,
Vol. 25 No. 1 (2013): Vol 25 Issue 1
Abstract
Fe(II), Co(II) and Ni(II) metal complexes of novel Schiff bases derived from cephalexin and sugars (D-glucose, D-xylose) were synthesized and characterized by physio-chemical (elemental analysis, magnetic susceptibility and electrolytic conductance) and spectral techniques. It has been found that Schiff bases behave as bidentate ligands forming complexes with 1:2 (metal:ligand) stoichiometry. Thermal behaviour of complexes has been investigated using thermogravimetric techniques. The biological activities of complexes have been evaluated against two gram negative (Escherichia coli and Pseudomonas aeruginosa) and two gram positive (Bacillus subtilis and Staphylococcus aureus) bacteria by Agar diffusion disc method. It has been found that the complexes have higher activity as compared to the pure cephalexin against the bacteria.
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- K. Singh, M.S. Barwa and P. Tyagi, Eur. J. Med. Chem., 42, 394 (2007).
- J.G. Lara, M. Masalha and S.J. Foster, Drug Discovery Today, 10, 643 (2005).
- S. Tehranchian, T. Akbarzadeh, M.R. Fazeli, H. Jamalifar and A. Shafiee, Bioorg. Med. Lett., 5, 1023 (2005).
- N. Gumrukcouglu, M. Serdar, E. Celik, A. Sevim and N. Demirbas, Turk. J. Chem., 31, 335 (2007).
- M.S. Iqbal, I.H. Bukhari and M. Arif, Appl. Organomet. Chem., 19, 864 (2005).
- G.B. Bagihalli, P.G. Avaji, S.A. Patil and P.S. Badami, Eur. J. Med. Chem., 43, 2639 (2008).
- N. Raman, J.D. Raja and A. Sakthivel, J. Chem. Sci., 119, 303 (2007).
- M.S. Iqbal,A.R. Ahmad, M. Sabir and S.M. Asad, J. Pharm. Pharmacol., 51, 371 (1999).
- Z.H. Chohan and M.F. Jaffery, Metal Based Drugs, 7, 265 (2000).
- R. Di Stefano, M. Scopelliti, C. Pellerito, T. Fiore, R. Vitturi, M.S. Colomba, P. Gianguzza, G.C. Stoccoa, M. Consiglioa and L. Pelleritoa, J. Inorg. Biochem., 89, 279 (2002).
- R. Ramesh and M. Sivagamasundari, Synth. React. Inorg. Met.-Org. Chem., 33, 809 (2003).
- P. Singh, R.L. Goel and B.P. Singh, J. Indian Chem. Soc., 52, 958 (1975).
- A.M. Mahindra, J.M. Fisher and Rabinovitz, Nature (London), 64, 303 (1983).
- M. Sonmez, Turk. J. Chem., 25, 181 (2001).
- K.S. Abou-Melha and H. Faruk, J. Iran. Chem. Soc., 5, 122 (2008).
- W. Radecka-Paryzek, V. Patroniak and J. Lisowski, Coord. Chem. Rev., 249, 2156 (2005).
- N. Raman, A. Kulandaisamy and K. Jeyasubramanian, Transition Met. Chem., 26, 131 (2001).
- M. Sonmez, Polish J. Chem., 77, 397 (2003).
- C. Spinu and A. Kriza, Acta Chim. Slov., 47, 179 (2000).
- S. Baluja, A. Aolanki and N. Kachhadia, J. Iran. Chem. Soc., 3, 312 (2006).
- N. Naz and M.Z. Iqbal, J. Chem. Soc. Pak., 31, 440 (2009).
- N. Naz and M.Z. Iqbal, Sci. Int., 23, 27 (2011).
- Z.H. Chohan and S.K.A. Sheazi, Synth. React. Inorg. Met.-Org. Chem., 29, 105 (1999).
- A.K. Halve, D. Bhadauria, B. Bhaskar, R. Dubey and S. Vasudha, Indian J. Pharm. Sci., 69, 680 (2007).
- V.K. Tandon, D.B. Yadav, R.V. Singh, M. Vaish, A.K. Chaturvedi and P.K. Shukla, Bioorg. Med. Chem., 15, 3463 (2007).
- A.K. Sadana, Y. Miraza, K.R. Aneja and O. Prakash, Eur. J. Med. Chem., 38, 533 (2003).
- D.E. Metzler, J. Am. Chem. Soc., 91, 627 (1968).
- M.S. Iqbal, S.J. Khurshid and M.Z. Iqbal,Can. J. Chem., 71, 629 (1993).
- S.M.E. Khalil, S.L. Stefan and K.A. Bashir, Synth. React. Inorg. Met.- Org. Chem., 29, 1685 (1999).
- M. Sekerci and E. Tas, Heteroatom Chem., 11, 254 (2000).
- B. Bosnich, J. Am. Chem. Soc., 90, 627 (1968).
- R.S. Downing and F.L. Urbach, J. Am. Chem. Soc., 91, 5977 (1969).
- M. Sonmez and M. Sekerci, Polish J. Chem., 76, 907 (2002).
- F.A. Cotton and G. Wilkinson, Advance Inorganic Chemistry, Academic Press, New York, edn. 4, p. 790 (1980).
- N.N. Green and A. Earnshaw, Chemistry of the Elements, Pergamon Press, Oxford, U.K., p. 1315 (1984).
- R.L. Duta and A. Syamal, Elements of Magnetochemistry, edn. 2 (1992).
- R. Di Stefano, M. Scopelliti, C. Pellerito, G. Casella, T. Fiore, G.C. Stocco, R. Vitturi, M. Colomba, L. Ronconi, I.D. Sciacca and L. Pellerito, J. Inorg. Biochem. 98, 534 (2004).
- P.K. Bhattacharrya and W.M. Cort,Analytical Profiles of Drug Substances, p. 28 (1978).
- E. Ivashikiv, Analytical Profiles of Drug Substances, p. 5 (1973).
- K. Nakamoto, Infrared and Raman Spectra of Inorganic and Coordination Compounds, New York, NY: John Wiley Interscience, p. 59 (1997).
- N. Raman, S. Ravichandran and A. Kulandaisamy, Asian J. Chem., 14, 1261 (2002).
- R.K. Agarwal, D. Sharma, L. Singh and H. Agarwal, Bioinorg. Chem. Appl., article 29234 (2006).
- Z.H. Chohan, M. Arif, M.A. Akhtar and C.T. Supuran, Bioinorg. Chem. Appl., article 83131 (2006).
- G.B. Deacon, F. Huber and R.J. Phillips, Inorg. Chim. Acta, 41, 104 (1985).
- X. Tai, X. Yin, Q. Chen and M. Tan, Molecules, 8, 439 (2003).
- N. Raman and S. Ravichandran, Polish J. Chem., 78 (2004).
- E. Canpolat and M. Kaya, Russian J. Chem., 31, 415 (2005).
- Z.H. Chohan, C.T. Supuran and A. Scozzafava, J. Enzyme Inhib. Med. Chem., 19, 79 (2004).
References
K. Singh, M.S. Barwa and P. Tyagi, Eur. J. Med. Chem., 42, 394 (2007).
J.G. Lara, M. Masalha and S.J. Foster, Drug Discovery Today, 10, 643 (2005).
S. Tehranchian, T. Akbarzadeh, M.R. Fazeli, H. Jamalifar and A. Shafiee, Bioorg. Med. Lett., 5, 1023 (2005).
N. Gumrukcouglu, M. Serdar, E. Celik, A. Sevim and N. Demirbas, Turk. J. Chem., 31, 335 (2007).
M.S. Iqbal, I.H. Bukhari and M. Arif, Appl. Organomet. Chem., 19, 864 (2005).
G.B. Bagihalli, P.G. Avaji, S.A. Patil and P.S. Badami, Eur. J. Med. Chem., 43, 2639 (2008).
N. Raman, J.D. Raja and A. Sakthivel, J. Chem. Sci., 119, 303 (2007).
M.S. Iqbal,A.R. Ahmad, M. Sabir and S.M. Asad, J. Pharm. Pharmacol., 51, 371 (1999).
Z.H. Chohan and M.F. Jaffery, Metal Based Drugs, 7, 265 (2000).
R. Di Stefano, M. Scopelliti, C. Pellerito, T. Fiore, R. Vitturi, M.S. Colomba, P. Gianguzza, G.C. Stoccoa, M. Consiglioa and L. Pelleritoa, J. Inorg. Biochem., 89, 279 (2002).
R. Ramesh and M. Sivagamasundari, Synth. React. Inorg. Met.-Org. Chem., 33, 809 (2003).
P. Singh, R.L. Goel and B.P. Singh, J. Indian Chem. Soc., 52, 958 (1975).
A.M. Mahindra, J.M. Fisher and Rabinovitz, Nature (London), 64, 303 (1983).
M. Sonmez, Turk. J. Chem., 25, 181 (2001).
K.S. Abou-Melha and H. Faruk, J. Iran. Chem. Soc., 5, 122 (2008).
W. Radecka-Paryzek, V. Patroniak and J. Lisowski, Coord. Chem. Rev., 249, 2156 (2005).
N. Raman, A. Kulandaisamy and K. Jeyasubramanian, Transition Met. Chem., 26, 131 (2001).
M. Sonmez, Polish J. Chem., 77, 397 (2003).
C. Spinu and A. Kriza, Acta Chim. Slov., 47, 179 (2000).
S. Baluja, A. Aolanki and N. Kachhadia, J. Iran. Chem. Soc., 3, 312 (2006).
N. Naz and M.Z. Iqbal, J. Chem. Soc. Pak., 31, 440 (2009).
N. Naz and M.Z. Iqbal, Sci. Int., 23, 27 (2011).
Z.H. Chohan and S.K.A. Sheazi, Synth. React. Inorg. Met.-Org. Chem., 29, 105 (1999).
A.K. Halve, D. Bhadauria, B. Bhaskar, R. Dubey and S. Vasudha, Indian J. Pharm. Sci., 69, 680 (2007).
V.K. Tandon, D.B. Yadav, R.V. Singh, M. Vaish, A.K. Chaturvedi and P.K. Shukla, Bioorg. Med. Chem., 15, 3463 (2007).
A.K. Sadana, Y. Miraza, K.R. Aneja and O. Prakash, Eur. J. Med. Chem., 38, 533 (2003).
D.E. Metzler, J. Am. Chem. Soc., 91, 627 (1968).
M.S. Iqbal, S.J. Khurshid and M.Z. Iqbal,Can. J. Chem., 71, 629 (1993).
S.M.E. Khalil, S.L. Stefan and K.A. Bashir, Synth. React. Inorg. Met.- Org. Chem., 29, 1685 (1999).
M. Sekerci and E. Tas, Heteroatom Chem., 11, 254 (2000).
B. Bosnich, J. Am. Chem. Soc., 90, 627 (1968).
R.S. Downing and F.L. Urbach, J. Am. Chem. Soc., 91, 5977 (1969).
M. Sonmez and M. Sekerci, Polish J. Chem., 76, 907 (2002).
F.A. Cotton and G. Wilkinson, Advance Inorganic Chemistry, Academic Press, New York, edn. 4, p. 790 (1980).
N.N. Green and A. Earnshaw, Chemistry of the Elements, Pergamon Press, Oxford, U.K., p. 1315 (1984).
R.L. Duta and A. Syamal, Elements of Magnetochemistry, edn. 2 (1992).
R. Di Stefano, M. Scopelliti, C. Pellerito, G. Casella, T. Fiore, G.C. Stocco, R. Vitturi, M. Colomba, L. Ronconi, I.D. Sciacca and L. Pellerito, J. Inorg. Biochem. 98, 534 (2004).
P.K. Bhattacharrya and W.M. Cort,Analytical Profiles of Drug Substances, p. 28 (1978).
E. Ivashikiv, Analytical Profiles of Drug Substances, p. 5 (1973).
K. Nakamoto, Infrared and Raman Spectra of Inorganic and Coordination Compounds, New York, NY: John Wiley Interscience, p. 59 (1997).
N. Raman, S. Ravichandran and A. Kulandaisamy, Asian J. Chem., 14, 1261 (2002).
R.K. Agarwal, D. Sharma, L. Singh and H. Agarwal, Bioinorg. Chem. Appl., article 29234 (2006).
Z.H. Chohan, M. Arif, M.A. Akhtar and C.T. Supuran, Bioinorg. Chem. Appl., article 83131 (2006).
G.B. Deacon, F. Huber and R.J. Phillips, Inorg. Chim. Acta, 41, 104 (1985).
X. Tai, X. Yin, Q. Chen and M. Tan, Molecules, 8, 439 (2003).
N. Raman and S. Ravichandran, Polish J. Chem., 78 (2004).
E. Canpolat and M. Kaya, Russian J. Chem., 31, 415 (2005).
Z.H. Chohan, C.T. Supuran and A. Scozzafava, J. Enzyme Inhib. Med. Chem., 19, 79 (2004).