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

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.

This is a preview of subscription content, access via your institution.

Scheme
Fig. 1.
Fig. 2.

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

Download references

Author information

Affiliations

Authors

Corresponding author

Correspondence to A. Saeed.

Ethics declarations

No conflict of interest was declared by the authors.

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

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

Download citation

Keywords:

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