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Molecules 2012, 17(3), 2316-2329; doi:10.3390/molecules17032316

Acylated mono-, bis- and tris- Cinchona-Based Amines Containing Ferrocene or Organic Residues: Synthesis, Structure and in Vitro Antitumor Activity on Selected Human Cancer Cell Lines

1
Institute of Chemistry, Eötvös Loránd University, P. O. B. 32, H-1518 Budapest-112, Hungary
2
Research Group of Peptide Chemistry, Hungarian Academy of Sciences, Eötvös Loránd Universiy, P. O. B. 32, H-1518 Budapest-112, Hungary
3
Chemres Institute of Structural Chemistry Chemical Research Center, Hungarian Academy of Sciences, H-1025 Budapest, Pusztaszeri str. 59-67, Hungary
4
Faculty of Chemistry and Chemical Engineering, Babes-Bolyai University, Arany János str. 11, 400028 Cluj-Napoca, Romania
*
Author to whom correspondence should be addressed.
Received: 9 January 2012 / Revised: 13 February 2012 / Accepted: 14 February 2012 / Published: 24 February 2012
(This article belongs to the Section Medicinal Chemistry)
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Abstract

A series of novel functionalized mono-, bis- and tris-(S)-{[(2S,4R,8R)-8-ethyl-quinuclidin-2-yl](6-methoxyquinolin-4-yl)}methanamines including ferrocene-containing derivatives was obtained by the reaction of the precursor amine with a variety of acylation agents. Their in vitro antitumor activity was investigated against human leukemia (HL-60), human neuroblastoma (SH-SY5Y), human hepatoma (HepG2) and human breast cancer (MCF-7) cells by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT)-assay and the 50% inhibitory concentration (IC50) values were determined. Our data indicate that the precursor amine has no antitumor activity in vitro, but the bis-methanamines with ureido-, thioureido and amide-type linkers display attractive in vitro cytotoxicity and cytostatic effects on HL-60, HepG2, MCF-7 and SH-SY5Y cells. Besides 1H- and 13C-NMR methods the structures of the new model compounds were also studied by DFT calculations.
Keywords: quinine; ferrocene; axial; symmetry; anticancer; activity; in vitro assay quinine; ferrocene; axial; symmetry; anticancer; activity; in vitro assay
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Károlyi, B.I.; Bősze, S.; Orbán, E.; Sohár, P.; Drahos, L.; Gál, E.; Csámpai, A. Acylated mono-, bis- and tris- Cinchona-Based Amines Containing Ferrocene or Organic Residues: Synthesis, Structure and in Vitro Antitumor Activity on Selected Human Cancer Cell Lines. Molecules 2012, 17, 2316-2329.

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