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, Szilvia Bősze, Erika Orbán, Pál Sohár, László Drahos, Emese Gál, Antal Csámpai
2012 Molecules  
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
more » ... phenyltetrazolium 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 1 H-and 13 C-NMR methods the structures of the new model compounds were also studied by DFT calculations.
doi:10.3390/molecules17032316 pmid:22367026 fatcat:4w6zycmrlbdsfimmvxkzfzzuca