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

Dalton transactions (Cambridge, England : 2003) (2009-01-29)
John Spencer, Andrew P Mendham, Arun K Kotha, Simon C W Richardson, Elizabeth A Hillard, Gérard Jaouen, Louise Male, Michael B Hursthouse
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Ferrocenecarboxaldehyde, 98%
Supelco
Ferrocenecarboxaldehyde, for HPLC derivatisation, LiChropur, ≥98.0% (HPLC)

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