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.
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Authors | John Spencer, Andrew P Mendham, Arun K Kotha, Simon C W Richardson, Elizabeth A Hillard, Gérard Jaouen, Louise Male, Michael B Hursthouse |
Journal | Dalton transactions (Cambridge, England : 2003)
(Dalton Trans)
Issue 6
Pg. 918-21
(Feb 14 2009)
ISSN: 1477-9226 [Print] England |
PMID | 19173072
(Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
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Chemical References |
- 3-ferrocenylmethylidene-1,3-dihydro-2H-indol-2-one
- Ferrous Compounds
- Indoles
- ferrocenecarboxaldehyde
- Vascular Endothelial Growth Factor Receptor-2
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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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