Copper Complexes of Imidazole-2-carbaldehyde N(4)-Substituted Thiosemicarbazones: Synthesis, Characterization and Antimicrobial Activity

Dilip Tiwari; Kanchan Basnet; Janardan Lamichhane; Prasodhan Niraula; Sunil Bhandari; Paras Nath Yadav

doi:10.14233/ajchem.2016.20127

Issue

Vol. 28 No. 12 (2016): Vol 28 Issue 12

Issue Published : September 1, 2016

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

Copper Complexes of Imidazole-2-carbaldehyde N(4)-Substituted Thiosemicarbazones: Synthesis, Characterization and Antimicrobial Activity

https://doi.org/10.14233/ajchem.2016.20127

Dilip Tiwari

Central Department of Chemistry, Tribhuvan University, Kirtipur, Kathmandu, Nepal

Kanchan Basnet

Central Department of Chemistry, Tribhuvan University, Kirtipur, Kathmandu, Nepal

Janardan Lamichhane

Department of Biotechnology, Kathmandu University, Dhulikhel, Kavre, Nepal

Prasodhan Niraula

Department of Biotechnology, Kathmandu University, Dhulikhel, Kavre, Nepal

Sunil Bhandari

Department of Biotechnology, Kathmandu University, Dhulikhel, Kavre, Nepal

Paras Nath Yadav

Central Department of Chemistry, Tribhuvan University, Kirtipur, Kathmandu, Nepal

Corresponding Author(s) : Paras Nath Yadav

paras_yadav2002@yahoo.com

Asian Journal of Chemistry, Vol. 28 No. 12 (2016): Vol 28 Issue 12
Article Published : September 2, 2016

Abstract

Imidazole-2-carbaldehyde N(4)-pyrrolidinyl, N(4)-piperidinyl, N(4)-morpholinyl and N(4)-piperazinyl thiosemicarbazones and their copper(II) complexes have been synthesized. The compounds were characterized by NMR, IR, UV-visible, ESR spectroscopy and ESI mass spectrometry. The stoichiometry, spectroscopic and mass spectrometry data indicates thiosemicarbazone coordination to Cu(II) in neutral form with NNS donors. The coordination spheres of the metal ion are completed by chlorine atoms in approximately square pyramidal geometry. The in vitro antimicrobial properties of the compounds in broth culture exhibited a moderate inhibitory effect on the microbial proliferation. Some copper(II) complexes exhibited a moderate inhibitory activity, better than that of the corresponding free thiosemicarbazone.

Keywords

Copper complex Imidazole Thiosemicarbazone Antimicrobial properties

Tiwari, D., Basnet, K., Lamichhane, J., Niraula, P., Bhandari, S., & Yadav, P. N. (2016). Copper Complexes of Imidazole-2-carbaldehyde N(4)-Substituted Thiosemicarbazones: Synthesis, Characterization and Antimicrobial Activity. Asian Journal of Chemistry, 28(12), 2793–2797. https://doi.org/10.14233/ajchem.2016.20127

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References

E.M. Jouad, G. Larcher, M. Allain, A. Riou, G.M. Bouet, M.A. Khan and X. Do Thanh, J. Inorg. Biochem., 86, 565 (2001); doi:10.1016/S0162-0134(01)00220-3. (and references therein).
E.M. Bavin, R.J.W. Rees, J.M. Robson, M. Seiler, D.E. Seymour and D. Suddaby, J. Pharm. Pharmacol., 2, 764 (1950); doi:10.1111/j.2042-7158.1950.tb12999.x.
O. Koch and G. Stuttgen, Arch. Exp. Pathol. Pharmakol., 210, 409 (1950).
D.X. West, S.B. Padhye and P.B. Sonawane, Struct. Bonding, 76, 1 (1991); doi:10.1007/3-540-53499-7_1.
M. Liu, T. Lin and A.C. Sartorelli, J. Med. Chem., 35, 3672 (1992); doi:10.1021/jm00098a012.
J.G. Cory, A.H. Cory, G. Rappa, A. Lorico, M.-C. Llu, T.-S. Lin and A.C. Sartorelli, Adv. Enzyme Regul., 35, 55 (1995); doi:10.1016/0065-2571(94)00005-N.
I. Krezel, Farmaco, 53, 342 (1998); doi:10.1016/S0014-827X(98)00031-7.
D.X. West, A.E. Liberta, S.B. Padhye, R.C. Chikate, P.B. Sonawane, A.S. Kumbhar and R.G. Yerande, Coord. Chem. Rev., 123, 49 (1993); doi:10.1016/0010-8545(93)85052-6.
J.P. Scovill, Phosphorus Sulfur Silicon Relat. Elem., 60, 15 (1991); doi:10.1080/10426509108233920.
F.E. Anderson, C.J. Duca and J.V. Scudi, J. Am. Chem. Soc., 73, 4967 (1951); doi:10.1021/ja01154a501.
M.C. Rodríguez-Argüelles, E.C. López-Silva, J. Sanmartín, A. Bacchi, C. Pelizzi and F. Zani, Inorg. Chim. Acta, 357, 2543 (2004); doi:10.1016/j.ica.2004.02.013.
H.M. Ericsson and J.C. Sherris, Acta Pathol. Microbiol. Scand. B Microbiol. Immunol., 217(Suppl.), 1 (1971).
D.X. West, M.A. Lockwood, J.N. Albert and A.E. Liberta, Spectrochim. Acta, 49, 1809 (1993); doi:10.1016/0584-8539(93)80250-E.
D.X. West, C.S. Carlson, K.J. Bouck and A.E. Liberta, Transition Met. Chem., 16, 271 (1991); doi:10.1007/BF01032851.
D.X. West, C.S. Carlson, A.E. Liberta and J.P. Scovill, Transition Met. Chem., 15, 383 (1990); doi:10.1007/BF01177467.
J.S. Casas, A. Castineiras, M.C. Rodriguez-Arguelles, A. Sanchez, J. Sordo, A. Vazquez-Lopez and E.M. Vazquez-Lopez, J. Chem. Soc., Dalton Trans., 2267 (2000); doi:10.1039/b002286l.
D.X. West, J.S. Ives, J. Krejci, M.M. Salberg, T.L. Zumbahlen, G.A. Bain, A.E. Liberta, J. Valdes-Martinez, S. Hernandez-ortiz and R.A. Toscano, Polyhedron, 14, 2189 (1995); doi:10.1016/0277-5387(95)00010-P.
D.X. West, M.A. Lockwood, M.D. Owens and A.E. Liberta, Transition Met. Chem., 22, 366 (1997); doi:10.1023/A:1018513919016.
M. Suzuki, H. Kanatomi, Y. Demura and I. Murase, Bull. Chem. Soc. Jpn., 57, 1003 (1984); doi:10.1246/bcsj.57.1003.
S. Chandra and L.K. Gupta, Spectrochim. Acta A, 61, 269 (2005); doi:10.1016/j.saa.2004.03.040.
M.H. Torre, D. Gambino, J. Araujo, H. Cerecetto, M. González, M.L. Lavaggi, A. Azqueta, A. López de Cerain, A.M. Vega, U. Abram and A.J. Costa-Filho, Eur. J. Med. Chem., 40, 473 (2005); doi:10.1016/j.ejmech.2004.11.012.
A. Winter, A. Zabel and P. Strauch, Int. J. Mol. Sci., 13, 1612 (2012); doi:10.3390/ijms13021612.
A. Bacchi, M. Carcelli, P. Pelagatti, C. Pelizzi, G. Pelizzi and F. Zani, J. Inorg. Biochem., 75, 123 (1999); doi:10.1016/S0162-0134(99)00045-8.

References

E.M. Jouad, G. Larcher, M. Allain, A. Riou, G.M. Bouet, M.A. Khan and X. Do Thanh, J. Inorg. Biochem., 86, 565 (2001); doi:10.1016/S0162-0134(01)00220-3. (and references therein).

E.M. Bavin, R.J.W. Rees, J.M. Robson, M. Seiler, D.E. Seymour and D. Suddaby, J. Pharm. Pharmacol., 2, 764 (1950); doi:10.1111/j.2042-7158.1950.tb12999.x.

O. Koch and G. Stuttgen, Arch. Exp. Pathol. Pharmakol., 210, 409 (1950).

D.X. West, S.B. Padhye and P.B. Sonawane, Struct. Bonding, 76, 1 (1991); doi:10.1007/3-540-53499-7_1.

M. Liu, T. Lin and A.C. Sartorelli, J. Med. Chem., 35, 3672 (1992); doi:10.1021/jm00098a012.

J.G. Cory, A.H. Cory, G. Rappa, A. Lorico, M.-C. Llu, T.-S. Lin and A.C. Sartorelli, Adv. Enzyme Regul., 35, 55 (1995); doi:10.1016/0065-2571(94)00005-N.

I. Krezel, Farmaco, 53, 342 (1998); doi:10.1016/S0014-827X(98)00031-7.

D.X. West, A.E. Liberta, S.B. Padhye, R.C. Chikate, P.B. Sonawane, A.S. Kumbhar and R.G. Yerande, Coord. Chem. Rev., 123, 49 (1993); doi:10.1016/0010-8545(93)85052-6.

J.P. Scovill, Phosphorus Sulfur Silicon Relat. Elem., 60, 15 (1991); doi:10.1080/10426509108233920.

F.E. Anderson, C.J. Duca and J.V. Scudi, J. Am. Chem. Soc., 73, 4967 (1951); doi:10.1021/ja01154a501.

M.C. Rodríguez-Argüelles, E.C. López-Silva, J. Sanmartín, A. Bacchi, C. Pelizzi and F. Zani, Inorg. Chim. Acta, 357, 2543 (2004); doi:10.1016/j.ica.2004.02.013.

H.M. Ericsson and J.C. Sherris, Acta Pathol. Microbiol. Scand. B Microbiol. Immunol., 217(Suppl.), 1 (1971).

D.X. West, M.A. Lockwood, J.N. Albert and A.E. Liberta, Spectrochim. Acta, 49, 1809 (1993); doi:10.1016/0584-8539(93)80250-E.

D.X. West, C.S. Carlson, K.J. Bouck and A.E. Liberta, Transition Met. Chem., 16, 271 (1991); doi:10.1007/BF01032851.

D.X. West, C.S. Carlson, A.E. Liberta and J.P. Scovill, Transition Met. Chem., 15, 383 (1990); doi:10.1007/BF01177467.

J.S. Casas, A. Castineiras, M.C. Rodriguez-Arguelles, A. Sanchez, J. Sordo, A. Vazquez-Lopez and E.M. Vazquez-Lopez, J. Chem. Soc., Dalton Trans., 2267 (2000); doi:10.1039/b002286l.

D.X. West, J.S. Ives, J. Krejci, M.M. Salberg, T.L. Zumbahlen, G.A. Bain, A.E. Liberta, J. Valdes-Martinez, S. Hernandez-ortiz and R.A. Toscano, Polyhedron, 14, 2189 (1995); doi:10.1016/0277-5387(95)00010-P.

D.X. West, M.A. Lockwood, M.D. Owens and A.E. Liberta, Transition Met. Chem., 22, 366 (1997); doi:10.1023/A:1018513919016.

M. Suzuki, H. Kanatomi, Y. Demura and I. Murase, Bull. Chem. Soc. Jpn., 57, 1003 (1984); doi:10.1246/bcsj.57.1003.

S. Chandra and L.K. Gupta, Spectrochim. Acta A, 61, 269 (2005); doi:10.1016/j.saa.2004.03.040.

M.H. Torre, D. Gambino, J. Araujo, H. Cerecetto, M. González, M.L. Lavaggi, A. Azqueta, A. López de Cerain, A.M. Vega, U. Abram and A.J. Costa-Filho, Eur. J. Med. Chem., 40, 473 (2005); doi:10.1016/j.ejmech.2004.11.012.

A. Winter, A. Zabel and P. Strauch, Int. J. Mol. Sci., 13, 1612 (2012); doi:10.3390/ijms13021612.

A. Bacchi, M. Carcelli, P. Pelagatti, C. Pelizzi, G. Pelizzi and F. Zani, J. Inorg. Biochem., 75, 123 (1999); doi:10.1016/S0162-0134(99)00045-8.

Issue

Vol. 28 No. 12 (2016): Vol 28 Issue 12

Copper Complexes of Imidazole-2-carbaldehyde N(4)-Substituted Thiosemicarbazones: Synthesis, Characterization and Antimicrobial Activity

Corresponding Author(s) : Paras Nath Yadav

Abstract

Keywords

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