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Molecules 2014, 19(10), 17026-17051; doi:10.3390/molecules191017026

Structural Diversity of Copper(II) Complexes with N-(2-Pyridyl)Imidazolidin-2-Ones(Thiones) and Their in Vitro Antitumor Activity

1
Department of Chemical Technology of Drugs, Faculty of Pharmacy, Medical University of Gdańsk, 80-416 Gdańsk, Poland
2
Department of Pharmaceutical and Medicinal Chemistry, Institute of Pharmacy, University of Greifswald, L.-F.-Jahn Str., D-17489 Greifswald, Germany
3
Faculty of Chemistry, A. Mickiewicz University, 60-780 Poznań, Poland
*
Author to whom correspondence should be addressed.
Received: 29 August 2014 / Revised: 30 September 2014 / Accepted: 13 October 2014 / Published: 23 October 2014
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Abstract

Six series of structurally different mono- and binuclear copper(II) complexes 510 were obtained by reacting N-(2-pyridyl)imidazolidin-2-ones (1al), N,N'-bis(2-pyridyl)imidazolidin-2-ones (2a,b), N-acyl-N'(2-pyridyl)imidazolodin-2-ones (3aj) and N-(2-pyridyl)imidazolidine-2-thiones (4ag) with copper(II) chloride at an ambient temperature. The coordination modes of the complexes obtained were established by elemental analysis, IR spectroscopic data and single crystal X-ray diffraction studies. The in vitro cytotoxic activities of both the free ligands and copper(II) complexes were evaluated using a crystal violet microtiter plate assay on five human tumor cell lines: LCLC-103H, A-427, SISO, RT-4 and DAN-G. The free ligands 14 at concentration attainable in cancer cells of 20 μM showed no meaningful cytotoxic effect with cell viability in the range of 88%–100%. The most potent copper(II) complex of 1-(6-ethoxy-2-pyridyl)imidazolidin-2-one (6b) exhibited selective cytotoxicity against A-427 lung cancer cell line, while the complexes of 1-(5-methyl-2-pyridyl)imidazolidine-2-thione (5h) and 1-(4-tert-butyl-2-pyridyl)imidazolidine-2-thione (5j) showed cytostatic effect against a whole panel of five human tumor cell lines. In conclusion, the only complexes that showed remarkably increased activity in comparison to the free ligands were those obtained from N-(2-pyridyl)imidazolidine-2-thiones 4c and 4e substituted with alkyl group at position 4 or 5 of pyridine ring. View Full-Text
Keywords: 1-(2-pyridyl)imidazolidin-2-ones; 1-(2-pyridyl)imidazolidine-2-thiones; copper(II) complexes; X-ray crystal structure analysis; in vitro antitumor activity 1-(2-pyridyl)imidazolidin-2-ones; 1-(2-pyridyl)imidazolidine-2-thiones; copper(II) complexes; X-ray crystal structure analysis; in vitro antitumor activity
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MDPI and ACS Style

Balewski, Ł.; Sączewski, F.; Bednarski, P.J.; Gdaniec, M.; Borys, E.; Makowska, A. Structural Diversity of Copper(II) Complexes with N-(2-Pyridyl)Imidazolidin-2-Ones(Thiones) and Their in Vitro Antitumor Activity. Molecules 2014, 19, 17026-17051.

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