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

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 readi...

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Published in:Dalton transactions : an international journal of inorganic chemistry 2009-01 (6), p.918-921
Main Authors: Spencer, John, Mendham, Andrew P, Kotha, Arun K, Richardson, Simon C W, Hillard, Elizabeth A, Jaouen, Gérard, Male, Louise, Hursthouse, Michael B
Format: Article
Language:English
Subjects:
Animals
Cell Line, Tumor
Cercopithecus 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
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Summary: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.
ISSN:1477-9226
1477-9234
DOI:10.1039/b816249b