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, Sz. Bősze, Erika Orbán, P. Sohár, L. Drahos, Emese Gál, A. Csámpai

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

A series of novel functionalized mono-, bis- and tris-(S)-{[(2S,4R,8R)-8- ethylquinuclidin-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 (IC 50) 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.

Original languageEnglish
Pages (from-to)2316-2329
Number of pages14
JournalMolecules
Volume17
Issue number3
DOIs
Publication statusPublished - Mar 2012

Fingerprint

Cinchona
Synthetic Chemistry Techniques
cultured cells
Amines
amines
cancer
Cells
acylation
Cell Line
Acylation
leukemias
Cytostatic Agents
synthesis
Cytotoxicity
cells
Discrete Fourier transforms
Amides
breast
amides
bromides

Keywords

  • Activity
  • Anticancer
  • Axial
  • Ferrocene
  • In vitro assay
  • Quinine
  • Symmetry

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "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",
abstract = "A series of novel functionalized mono-, bis- and tris-(S)-{[(2S,4R,8R)-8- ethylquinuclidin-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 (IC 50) 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.",
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author = "K{\'a}rolyi, {Benedek Imre} and Sz. Bősze and Erika Orb{\'a}n and P. Soh{\'a}r and L. Drahos and Emese G{\'a}l and A. Cs{\'a}mpai",
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T1 - Acylated mono-, bis- and tris-cinchona-based amines containing ferrocene or organic residues

T2 - Synthesis, structure and in vitro antitumor activity on selected human cancer cell lines

AU - Károlyi, Benedek Imre

AU - Bősze, Sz.

AU - Orbán, Erika

AU - Sohár, P.

AU - Drahos, L.

AU - Gál, Emese

AU - Csámpai, A.

PY - 2012/3

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AB - A series of novel functionalized mono-, bis- and tris-(S)-{[(2S,4R,8R)-8- ethylquinuclidin-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 (IC 50) 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.

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KW - Symmetry

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