Structural and biological investigation of ferrocene-substituted 3-methylidene-1,3-dihydro-2H-indol-2-ones

Dalton Trans. 2009 Feb 14:(6):918-21. doi: 10.1039/b816249b. Epub 2008 Nov 18.

Abstract

The Knoevenagel condensation of 1,3-dihydro-2H-indol-2-one with ferrocene carboxaldehyde afforded an approximate 2:1 mixture of the geometrical isomers (E)- and (Z)-3-ferrocenylmethylidene-1,3-dihydro-2H-indol-2-one respectively in an overall 67% yield; the air and solution-stable isomers were readily separated by preparative thin layer chromatography and their structures were unequivocally elucidated in solution, by (1)H NMR spectroscopy, and in the solid phase, by X-ray crystallography; both isomers of displayed in vitro toxicity against B16 melanoma and Vero cell lines in the micromolar range and inhibited the kinase VEGFR-2 with IC(50) values of ca. 200 nM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Line, Tumor
  • Chlorocebus aethiops
  • Crystallography, X-Ray
  • Ferrous Compounds / chemical synthesis
  • Ferrous Compounds / chemistry*
  • Ferrous Compounds / pharmacology
  • Indoles / chemical synthesis
  • Indoles / chemistry*
  • Inhibitory Concentration 50
  • Mice
  • Stereoisomerism
  • Vascular Endothelial Growth Factor Receptor-2 / antagonists & inhibitors
  • Vero Cells

Substances

  • 3-ferrocenylmethylidene-1,3-dihydro-2H-indol-2-one
  • Ferrous Compounds
  • Indoles
  • ferrocenecarboxaldehyde
  • Vascular Endothelial Growth Factor Receptor-2