Synthesis, Structural, DFT, and Cytotoxicity Studies of CuII and NiII Complexes with 3-Aminopyrazole Derivatives*.

Berta Holló; Vukadin M. Leovac; Petra Bombicz; Attila Kovács; Ljiljana S. Jovanović; Gordana Bogdanović; Vesna Kojić; Vladimir Divjaković; Milan D. Joksović; Katalin Mészáros Szécsényi

doi:10.1071/CH10210

RESEARCH ARTICLE

Synthesis, Structural, DFT, and Cytotoxicity Studies of Cu^II and Ni^II Complexes with 3-Aminopyrazole Derivatives*.

Berta Holló ^A , Vukadin M. Leovac ^A , Petra Bombicz ^B , Attila Kovács ^C ^D , Ljiljana S. Jovanović ^A , Gordana Bogdanović ^E , Vesna Kojić ^E , Vladimir Divjaković ^A , Milan D. Joksović ^F and Katalin Mészáros Szécsényi ^A ^G

+ Author Affiliations

- Author Affiliations

^A Faculty of Sciences, University of Novi Sad, Trg D.Obradovića 3,21000 Novi Sad, Serbia.

^B Institute of Structural Chemistry, Chemical Research Centre, Hungarian Academy of Sciences, PO Box 17, H-1525 Budapest, Hungary.

^C Research Group for Materials Structure and Modeling of the Hungarian Academy of Sciences, Budapest, University of Technology and Economics,H-1111 Budapest, Szt. Gellért tér 4, Hungary.

^D European Commission, Joint Research Centre, Institute for Transuranium Elements, PO Box 2340, 76125 Karlsruhe, Germany.

^E Institute of Oncology Sremska Kamenica, Institutski put 4,21204 Sremska Kamenica, Serbia.

^F Faculty of Sciences, University of Kragujevac, R. Domanovića 12,34000 Kragujevac, Serbia.

^G Corresponding author. Email: mszk@uns.ac.rs

Australian Journal of Chemistry 63(11) 1557-1564 https://doi.org/10.1071/CH10210
Submitted: 24 May 2010 Accepted: 18 August 2010 Published: 11 November 2010

Abstract

Template synthesis of N,N′-bis(4-acetyl-5-methylpyrazole-3-yl)formamidine (ampf) was performed starting from 4-acetyl-3-amino-5-methylpyrazole (aamp) and CH(OC₂H₅)₃ in methanol in the presence of CuCl₂, Cu(NO₃)₂, or Ni(NO₃)₂. The ligand was isolated in coordinated form as [Cu(ampf)Cl₂], [Cu(ampf)(MeOH)(NO₃)₂]MeOH, and [Ni(ampf)(MeOH)₂(NO₃)]NO₃ correspondingly. The compounds were characterized by elemental analysis, Fourier-transform IR and electronic spectroscopy, thermal analysis, single-crystal X-ray diffraction, and quantum chemical (density functional theory) calculations. The density functional theory calculations provided information on the metal–ligand interactions in the complexes and assisted the assignment of the FT-IR spectra. The antiproliferative activity of the complexes and the ligand precursor, aamp, was tested against human myelogenous leukaemia K562, colon adenocarcinoma HT29, and cervix carcinoma HeLa.

Acknowledgements

The work was financed in part by the Ministry of Science and Technological Development of the Republic of Serbia (grant no. 142028) and the Provincial Secretariat for Science and Technological Development of Vojvodina, Republic of Serbia. Additionally, grant no. 114–451–02011/2007–02, Provincial Secretariat for Science and Technological Development of Vojvodina, and Central European Exchange Program for University Studies (project no. CII-CZ-0212–02–0910) are gratefully acknowledged by B.H. and K.M.Sz. The authors would like to thank Dr Ivana Radosavljević Evans (Academic Fellow in Structural/Materials Chemistry, Department of Chemistry, University of Durham) for measuring the crystal data of [Cu(ampf)Cl₂].

References

*Part 30, Transition metal complexes with pyrazole‐based ligands.

Synthesis, Structural, DFT, and Cytotoxicity Studies of CuII and NiII Complexes with 3-Aminopyrazole Derivatives*.

Abstract

Acknowledgements

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Synthesis, Structural, DFT, and Cytotoxicity Studies of Cu^II and Ni^II Complexes with 3-Aminopyrazole Derivatives*.