Synthesis and Structure of 4-Chloro-2-{[5-(diethylamino)-2-hydroxybenzylidene]amino}phenol and Its Metal Complexes

Russian Journal of General Chemistry volume 90, pages2376–2380(2020)Cite this article

Abstract

The present study is devoted to the synthesis of 4-chloro-2-{[5-(diethylamino)-2-hydroxybenzylidene]amino}phenol and its transition metal complexes. Synthesis of the ligand has been achieved by the condensation reaction of N,N-diethylsalicylaldehyde with 4-chloro-2-aminophenol in acidic medium. Metals complexes of the ligand with different transition metal ions [M2+= Mn(II), Fe(II), Co(II), Ni(II), Cu(II), Zn(II), Cd(II), Hg(II), and Pd(II)] have been accumulated in alcoholic media and characterized by spectroscopic methods. UV-Vis analysis of the complexes indicates the ligand coordination to the metal ions via both OH groups and the azomethine nitrogen atom, acting as a tridentate ligand. Anticancer tests of selected complexes demonstrate moderate in vitro activity of Cu(II) complex against HeLa cell line.

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REFERENCES

  1. 1

    Adly, O.M., Spec. Acta. Part A: Nol. Bio. Spec., 2012, vol. 95, p. 483. https://doi.org/10.1016/j.saa.2012.04.030

  2. 2

    Jana, S., Bhowmik, P., Das, M., Jana, P.P., Harms, K., and Chattopadhyay, S., Polyhedron., 2012, vol. 37, no. 1, p. 21. https://doi.org/10.1016/j.poly.2012.01.031

    CAS  Article  Google Scholar 

  3. 3

    Kakanejadifard, A., Azarbani, F., Zabardasti, A., Rezayat, A., Ghasemian, M., and Kakanejadifard, S., Spec. Acta. Part A. Mol. Bio. Spec., 2013, vol. 114, p. 404. https://doi.org/10.1016/j.saa.2013.05.027

  4. 4

    Kakanejadifard, A., Azarbani, F., Saki, Z., Kakanejadifard, S., and Zabardasti, A., Spec. Acta. Part A. Mol. Bio. Spec., 2014, vol. 132, p. 700. https://doi.org/10.1016/j.saa.2014.04.181

  5. 5

    Singh, H.L., Varshney, S., and Varshney, A.K., App. Org. Chem., 2000, vol. 14, no. 4, p. 212. https://doi.org/10.1002/(SICI)1099-0739(200004)14:4<212::AID-AOC980>3.0.CO;2-H

  6. 6

    Wang, M., Wang, L.F., Li, Y.Z., Li, Q.X., Xu, Z.D., and Qu, D.M., Trans. Met. Chem., 2001, vol. 26, no. 3, p. 307. https://doi.org/10.1023/A:1007159301849

    CAS  Article  Google Scholar 

  7. 7

    Gulerman, N.N., Rollas, S., Erdeniz, H., and Kiraz, M., J. Pharm. Sci., 2001, vol. 26, p. 1.

  8. 8

    Charo, J., Lindencrona, J.A., Carlson, L.M., Hinkula, J., and Kiessling, R., J. Virology., 2004, vol. 78, no. 20, p. 11321. https://doi.org/10.1128/JVI.78.20.11321-11326.2004

    CAS  Article  PubMed  Google Scholar 

  9. 9

    Abbas, N., Tirmizi, S.A., Shabir, G., Saeed, A., Hussain, G., Channer, P.A., Saleem, R., and Ayaz, M., Inorg. NanoMetal. Chem., 2018, vol. 48, no. 1, p. 57. https://doi.org/10.1080/24701556.2017.1357632

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Affiliations

  1. Department of Chemistry, Quaid-i-Azam University, 45320, Islamabad, Pakistan

    N. Abbas, G. Shabir, A. Saeed & S. A. Tirmizi

  2. Departamento de Física, Facultad de Ciencias Exactas, Universidad Nacional de La Plata and Institute IFLP (CONICET, CCT-La Plata), 1900, La Plata, Argentina

    G. A. Echeverría & O. E. Piro

  3. CEQUINOR (UNLP, CONICET-CCT La Plata), Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, 1900, La Plata, Argentina

    M. F. Erben

Authors
  1. N. Abbas
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  2. G. Shabir
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  3. A. Saeed
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  4. S. A. Tirmizi
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  5. G. A. Echeverría
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  6. O. E. Piro
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  7. M. F. Erben
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Correspondence to A. Saeed.

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Abbas, N., Shabir, G., Saeed, A. et al. Synthesis and Structure of 4-Chloro-2-{[5-(diethylamino)-2-hydroxybenzylidene]amino}phenol and Its Metal Complexes. Russ J Gen Chem 90, 2376–2380 (2020). https://doi.org/10.1134/S1070363220120233

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Keywords:

  • anticancer activity
  • HeLa cell line
  • azomethine
  • condensation reaction
  • spectroscopic methods