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Synthesis, structure analysis, anti-bacterial and in vitro anti-cancer activity of new Schiff base and its copper complex derived from sulfamethoxazole

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Abstract

A new bidentate Schiff base ligand (HL1), containing O,N donors was prepared by the reaction of sulfamethoxazole with 5-nitrosalicylaldehyde and characterized by elemental analysis, FT-IR, 1H and13C NMR. The copper complex of this ligand was synthesised by treating DMF-ethanolic mixture solution of the ligand of two equivalents with one equivalent of copper acetate. The complex was characterized on the basis of UV, FT-IR, molar conductance, EPR, magnetic moment and single crystal X-ray diffraction. Interestingly, the crystal structure of the octahedral complex showed two solvent molecules (DMF) as ligands at their axial positions. The molar conductance data revealed that the complex is a non-electrolyte. The Schiff base and its copper complex have been investigated as anti-bacterial and anti-fungal agents against various microorganisms. The in vitro cytotoxicity tests of the ligand and its copper complex were carried out in two different human tumour cell lines, HCT-116 and MDA – MB - 231. The cytotoxicity studies showed that the complex exhibited higher activity than cisplatin and carboplatin towards MDA – MB – 231.

A new Schiff base (HL1) is formed by condensation of sulfamethoxazole and 5–nitro salicylaldehyde, which on reaction with copper acetate in DMF–ethanol mixture gives [Cu(L1)2(DMF)2] complex. Analytical, structural, spectral and molar conductivity measurements were used to investigate the chemical structure of the ligand and its complex. The synthesized complex was screened for in vitro anti-microbial and anti-cancer activity.

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Acknowledgements

The authors are thankful to the Director, SAIF, IIT, Chennai, STIC, Cochin, Kerala, CECRI, Karaikudi and SRM University, Kattankulathur for providing analytical support. The authors also thank the Secretary, Principal and Faculty members of Chemistry, Seethalakshmi Ramaswami College, Trichy, Tamil Nadu for providing laboratory facilities and support.

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  1. PG and Research Department of Chemistry, Seethalakshmi Ramaswami College, Tiruchirappalli, 620 002, Tamil Nadu, India

    I RAMA & R SELVAMEENA

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Correspondence to I RAMA.

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Supplementary Information

CCDC 985349 contains the supplementary crystallographic data for NSSMOCu. These data can be obtained free of charge via http://www.ccdc.cam.ac.uk/conts/retrieving.html, or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: (+ 44)1223-336-033; or e-mail: deposit@ccdc.cam.ac.uk. Supplementary information on elemental analysis data, EPR and NMR spectra are available at www.ias.ac.in/chemsci.

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RAMA, I., SELVAMEENA, R. Synthesis, structure analysis, anti-bacterial and in vitro anti-cancer activity of new Schiff base and its copper complex derived from sulfamethoxazole. J Chem Sci 127, 671–678 (2015). https://doi.org/10.1007/s12039-015-0824-z

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