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

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.
AuthorsJohn Spencer, Andrew P Mendham, Arun K Kotha, Simon C W Richardson, Elizabeth A Hillard, Gérard Jaouen, Louise Male, Michael B Hursthouse
JournalDalton transactions (Cambridge, England : 2003) (Dalton Trans) Issue 6 Pg. 918-21 (Feb 14 2009) ISSN: 1477-9226 [Print] England
PMID19173072 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
Chemical References
  • 3-ferrocenylmethylidene-1,3-dihydro-2H-indol-2-one
  • Ferrous Compounds
  • Indoles
  • ferrocenecarboxaldehyde
  • Vascular Endothelial Growth Factor Receptor-2
Topics
  • Animals
  • Cell Line, Tumor
  • Chlorocebus aethiops
  • Crystallography, X-Ray
  • Ferrous Compounds (chemical synthesis, chemistry, pharmacology)
  • Indoles (chemical synthesis, chemistry)
  • Inhibitory Concentration 50
  • Mice
  • Stereoisomerism
  • Vascular Endothelial Growth Factor Receptor-2 (antagonists & inhibitors)
  • Vero Cells

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