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

Spencer, John, Mendham, Andrew P, Kotha, Arun K, Richardson, Simon C W, Hillard, Elizabeth A, Jaouen, Gérard, Male, Louise and Hursthouse, Michael B (2009) Structural and biological investigation of ferrocene-substituted 3-methylidene-1,3-dihydro-2H-indol-2-ones. Dalton Transactions, 38 (6). pp. 918-921. ISSN 1477-9226

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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.

Item Type: Article
Keywords: estrogen-receptor modulators, tyrosine kinase-activity, breast-cancer, in-vitro, inhibitors, antimalarial, chloroquine, ferrocifens, activation, chemistry
Schools and Departments: School of Life Sciences > Chemistry
Subjects: Q Science
Depositing User: Deeptima Massey
Date Deposited: 22 Oct 2012 11:17
Last Modified: 02 Jul 2013 13:14
URI: http://srodev.sussex.ac.uk/id/eprint/40926
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