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

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. (2008) Structural and biological investigation of ferrocene-substituted 3-methylidene-1,3-dihydro-2H-indol-2-ones. Dalton Transactions, 2009 (6). pp. 918-921. ISSN 1477-9226 (Print), 1477-9234 (Online) (doi:10.1039/B816249B)

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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
Additional Information: [1] First published online: 18 November 2008. [2] First published in print: 14 February 2009. [3] Published as: Dalton Transactions, 2009, (6) 918-921.
Uncontrolled Keywords: estrogen-receptor modulators, tyrosine kinase-activity, breast-cancer, in-vitro, inhibitors, antimalarial, chloroquine, ferrocifens, activation, chemistry
Subjects: Q Science > QD Chemistry
R Medicine > RC Internal medicine > RC0254 Neoplasms. Tumors. Oncology (including Cancer)
R Medicine > RM Therapeutics. Pharmacology
Faculty / Department / Research Group: Faculty of Engineering & Science > Department of Pharmaceutical, Chemical & Environmental Sciences
Related URLs:
Last Modified: 17 Oct 2016 09:09
Selected for GREAT 2016: None
Selected for GREAT 2017: None
Selected for GREAT 2018: None
URI: http://gala.gre.ac.uk/id/eprint/1600

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