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

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

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Received: 9 January 2012; in revised form: 13 February 2012 / Accepted: 14 February 2012 / Published: 24 February 2012
(This article belongs to the Section Medicinal Chemistry)
Download PDF [253 KB, uploaded 18 June 2014]
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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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.

AMA Style

Károlyi BI, 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(3):2316-2329.

Chicago/Turabian Style

Károlyi, Benedek Imre; Bősze, Szilvia; Orbán, Erika; Sohár, Pál; Drahos, László; Gál, Emese; Csámpai, Antal. 2012. "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 17, no. 3: 2316-2329.


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