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Issue 6, 2009
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Structural and biological investigation of ferrocene-substituted 3-methylidene-1,3-dihydro-2H-indol-2-ones

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Abstract

The Knoevenagel condensation of 1,3-dihydro-2H-indol-2-one 1 with ferrocene carboxaldehyde 2 afforded an approximate 2:1 mixture of the geometrical isomers (E)- and (Z)-3-ferrocenylmethylidene-1,3-dihydro-2H-indol-2-one 3 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 1H NMR spectroscopy, and in the solid phase, by X-ray crystallography; both isomers of 3 displayed in vitro toxicity against B16 melanoma and Vero cell lines in the micromolar range and inhibited the kinase VEGFR-2 with IC50 values of ca. 200 nM.

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

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Publication details

The article was received on 17 Sep 2008, accepted on 06 Nov 2008 and first published on 18 Nov 2008


Article type: Communication
DOI: 10.1039/B816249B
Citation: Dalton Trans., 2009,0, 918-921
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    Structural and biological investigation of ferrocene-substituted 3-methylidene-1,3-dihydro-2H-indol-2-ones

    J. Spencer, A. P. Mendham, A. K. Kotha, S. C. W. Richardson, E. A. Hillard, G. Jaouen, L. Male and M. B. Hursthouse, Dalton Trans., 2009, 0, 918
    DOI: 10.1039/B816249B

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