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

Benedek Imre Károlyi 1 email, Szilvia Bősze 2 email, Erika Orbán 2 email, Pál Sohár 1 email, László Drahos 3 email, Emese Gál 4 email and Antal Csámpai 1,* email
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; in revised form: 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

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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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