Skip to main content
SpringerLink
Log in

Spectroscopic and anticancer studies on new synthesized copper(II) and manganese(II) complexes with 1,2,4-triazines thiosemicarbazide

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

Binuclear Cu(II) and Mn(II) newly transition metal complexes of the 5-benzylidene-3-(4-chlorophenyl)-6-oxo-5,6-dihydro-1H-[1,2,4]triazine-2-carbothioic acid amide (HL1) and 5-(3-bromo-4-methoxybenzylidene)-3-(4-chloro-phenyl)-6-oxo-5,6-dihydro-1H-[1,2,4]triazine-2-carbothioic acid amide (HL2) derived from the condensation of oxazolinone with thiosemicarbazide have been prepared. The structural elucidation was discussed upon elemental analyses and molar conductivity, as well as from mass, 1H NMR, IR, UV-Vis spectral studies. From the analytical, spectroscopic and thermal data, the stoichiometry of the mentioned complexes was found to be 1: 2 (metal: ligand). The molar conductance data revealed that all the metal chelates are non-electrolytes and the sulphato ions existing inside of the coordination sphere. The thermal stabilities of these complexes were studied by thermogravimetric (TG-DTG/DTA) and the decomposition steps of these complexes are investigated. The kinetic thermodynamic parameters such as the energy of activation (E*), pre-exponential factor (A), activation entropy (ΔS*), activation enthalpy (ΔH*) and free energy of activation (ΔG*) have been calculated. Inhibitory activity against breast carcinoma cells (MCF-7 cell line), hepatocellular carcinoma cells (HePG-2 cell line) and colon carcinoma cells (HCT cell line) were tested by using different concentrations of the samples (50, 25, 12.5, 6.25, 3.125, and 1.56 μg) and cell viability (%) was determined by colorimetric method. The drug doxrubcin was used as standard.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Chohan, Z.H., Farooq, M.A., Scozzafava, A., and Supuran, C.T., J. Enzyme Inhib. Med. Chem., 2002, vol. 17, no. 1, p. 1.

    Article  CAS  Google Scholar 

  2. Singh, K., Barwa, M.S., and Tyagi, P., Eur. J. Med. Chem., 2006, vol. 41, no. 1, p. 147.

    Article  Google Scholar 

  3. Singh, K., Singh, D.P., Barwa, M.S., Tyagi, P., and Mirza, Y., J. Enzym. Inhib. Med. Chem., 2006, vol. 21, no. 5, p. 557.

    Article  CAS  Google Scholar 

  4. Cozzi, P.G., Chem. Soc. Rev., 2004, vol. 33, p. 410.

    Article  CAS  Google Scholar 

  5. Jarrahpour, A.A. and Zarei, M., Molbank M377, 2004.

    Google Scholar 

  6. Chandra, S. and Sangeetika, J., J. Indian Chem. Soc., 2004, vol. 81, no. 3, p. 203.

    CAS  Google Scholar 

  7. More, P.G. and Bhalvankar, R.B., J. Indian Chem. Soc., 2004, vol. 81, no. 1, p. 13.

    CAS  Google Scholar 

  8. Yildiz, M., Dulger, B., Koyuncu, S.Y., and Yapici, B.M., J. Indian Chem. Soc., 2007, vol. 81, no. 1, p. 7.

    Google Scholar 

  9. Islam, M.S., Farooque, M.A., Bodruddoza, M.A.K., Mosaddik, M.A., and Alam, M.S., J. Biol. Sci., 2003, vol. 2, no. 12, p. 797.

    Google Scholar 

  10. Ferrari, M.B., Capacchi, S., Pelosi, G., Reffo, G., Tarasconi, P., Albertini, R., Pinelli, S., and Lunghi, P., Inorg. Chim. Acta, 1999, vol. 286, no. 2, p. 134.

    Article  Google Scholar 

  11. Chohan, Z.H., Pervez, H., Khan, K.M., Rauf, A., and Supuran, C.T., J. Enzyme Inhib. Med. Chem., 2004, vol. 19, no. 1, p. 51.

    Article  CAS  Google Scholar 

  12. Canpolat, E. and Kaya, M., J. Coord. Chem., 2004, vol. 57, no. 14, p. 1217.

    Article  CAS  Google Scholar 

  13. Singh, G., Singh, Ph.A., Sen, A.K., Singh, K., Dubey, S.N., Handa, R.N., and Choi, J., Synth. React. Inorg. Met. Org. Chem., 2002, vol. 32, no. 1, p. 171.

    Article  CAS  Google Scholar 

  14. Croot, P.L. and Hunter, K.A., Anal. Chim. Acta, 2000, vol. 406, p. 289; Almog, J., Hirshfeld, A., Glattstein, B., and Sterling, J., Z. Goren, Anal. Chim. Acta, 1996, vol. 322, p. 203.

    Article  CAS  Google Scholar 

  15. Katano, H., Kuboyama, H., and Senda, M., J. Electroanal. Chem., 2000, vol. 483, p. 117

    Article  CAS  Google Scholar 

  16. Uma, R., Palaniandavar, M., and Butcher, R.J., J. Chem. Soc., Dalton Trans., 1996, vol. 10, p. 2061.

    Article  Google Scholar 

  17. Zhu, B., Schechtman, S., and Chevion, M., US Patent WO 9939575, 1999.

  18. Torres, E.L. and Mendiola, M.A., Polyhedron, 2005, vol. 24, p. 1435.

    Article  Google Scholar 

  19. Singh, K., Kumar, Y., Puri, P., Sharma, C., and Aneja, K.R., Inter. J. Inorg. Chem., 2012, no. 2012, p. 1.

    Google Scholar 

  20. Mohamed, G.G., Badawy, M.A., Nassar, M.M., and Kamel, A.B., Spect. Chim. Acta A, 2010, vol. 77, p. 773.

    Article  Google Scholar 

  21. Neunhoeffer, H., in Comprehensive Heterocyclic Chemistry, Katritzky, A.R. and Rees, C.W., Eds., Oxford: Pergamon Press, 1984, vol. 3, pp. 385–456.

    Google Scholar 

  22. Mura, P., Olby, B.G., and Robinson, S.D., J. Chem. Soc., Dalton Trans., 1985, no. 10, p. 2101.

    Google Scholar 

  23. Ghassemzadeh, M., Aghayan, M.M., and Neumuller, B., Inorg. Chim. Acta, 2005, no. 358, p. 2057.

    Google Scholar 

  24. Zhang, H.X., Kato, M., Sasaki, Y., Ohba, T., Ito, H., Kobayashi, A., and Chang, H.C., Uosaki, 2012, vol. 41, p. 11497.

    CAS  Google Scholar 

  25. Machura, B., Switlicka, A., Kruszynski, R., Mrozinski, J., Klak, J., and Kusz, J., Polyhedron, 2008, vol. 27, p. 2959.

    Article  CAS  Google Scholar 

  26. Bereau, V., Rey, J., Deydier, E., and Marrot, J., Inorg.Chim Acta, 2003, no. 351, p. 389.

    Google Scholar 

  27. Singh, K., Barwa, M.S., and Tyagi, P., Eur. J. Med. Chem., 2007, vol. 42, p. 394.

    Article  CAS  Google Scholar 

  28. Singh, N.K. and Srivastava, A., Trans. Met. Chem., 2000, vol. 25, p. 133.

    Article  CAS  Google Scholar 

  29. Wang, M., Wang, L.F., Ligands, Y.Z., and Li, Q.X., Trans. Met. Chem., 2001, vol. 26, p. 307

    Article  CAS  Google Scholar 

  30. Li, M.X., Zhang, L.Z., Zhang, D., Ji, B.S., and Zhao, J.W., Eur. J. Med. Chem., 2011, vol. 46, no. 9, p. 4383.

    Article  CAS  Google Scholar 

  31. Vyas, K.M., Joshi, R.G., Jadeja, R.N., Prabha, C.R., and Gupta, V.K., Spectrochim. Acta A, 2011, vol. 84, no. 1, p. 256.

    Article  CAS  Google Scholar 

  32. Belicchi-Ferrai, M., Biscegli, F., Pelosi, G., Pinelli, S., and Traascani, P., Polyhedron, 2007, vol. 26, p. 5150

    Article  Google Scholar 

  33. Majumder, A., Chaudrary, C.R., Mitra, S., and Dahlenburg, L., Struct. Chem., 2005, vol. 16, p. 611

    Article  Google Scholar 

  34. Vogel, A.I., A Text Book of Quantitative Inorganic Analysis, London: Longman, 1994.

    Google Scholar 

  35. Mosmann, T., J. Immunol. Methods, 1983, vol. 65, p. 55.

    Article  CAS  Google Scholar 

  36. Vijayan, P., Raghu, C., Ashok, G., Dhanaraj, S.A., and Suresh, B., Indian J. Med. Res., 2004, vol. 120, p. 24.

    CAS  Google Scholar 

  37. Franco, E., Lopez-Trorres, El, Mendiola, M.A., and Sevilla, M.T., Polyhedron, 2000, vol. 19, p. 441.

    Article  CAS  Google Scholar 

  38. Nakamoto, K., Infrared and Raman Spectra of Coordination Compounds, New York: Wiley-Interscience, 1970.

    Google Scholar 

  39. Filo, J.J., Terron, A., Mulet, D., and Merno, V., Inorg. Chim. Acta., 1987, vol. 135, p. 197.

    Article  Google Scholar 

  40. Lever, A.B.P., Crystal Field Spectra Inorganic Electronic Spectroscopy, 1 ed., Amsterdam: Elsevier, 1968, p. 249

    Google Scholar 

  41. HyperChem Professional 7.5, Hypercube, Inc., Gainesville, FL 32601, USA, 2002. http://www.hyper.com.

  42. Coats, A.W. and Redfern, J.P., Nature, 1964, vol. 201, p. 68.

    Article  CAS  Google Scholar 

  43. Horowitz, H.W. and Metzger, G., Anal. Chem., 1963, vol. 35, p. 1464.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Taif University, Al-Hawiah, Taif, P.O. Box 888, Zip Code 21974, Saudi Arabia

    Moamen S. Refat

  2. Department of Chemistry, Faculty of Science, Port Said University, Port Said, Egypt

    Moamen S. Refat, I. M. El-Deen, M. S. El-Garib & W. Abd El-Fattah

Authors
  1. Moamen S. Refat
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. I. M. El-Deen
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. S. El-Garib
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. W. Abd El-Fattah
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Moamen S. Refat.

Additional information

The text was submitted by the authors in English.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Refat, M.S., El-Deen, I.M., El-Garib, M.S. et al. Spectroscopic and anticancer studies on new synthesized copper(II) and manganese(II) complexes with 1,2,4-triazines thiosemicarbazide. Russ J Gen Chem 85, 692–707 (2015). https://doi.org/10.1134/S1070363215030299

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363215030299

Keywords

Search

Navigation