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Size does matter. Sterically demanding metallocene-substituted 3-methylidene-oxindoles exhibit poor kinase inhibitory action

Size does matter. Sterically demanding metallocene-substituted 3-methylidene-oxindoles exhibit poor kinase inhibitory action

Spencer, John, Amin, Jahangir, Coxhead, Peter, McGeehan, John, Richards, Christopher J., Tizzard, Graham J., Coles, Simon J., Bingham, John P., Hartley, John A., Feng, Li, Meggers, Eric and Guille, Matthew (2011) Size does matter. Sterically demanding metallocene-substituted 3-methylidene-oxindoles exhibit poor kinase inhibitory action. Organometallics, 30 (11). pp. 3177-3181. ISSN 0276-7333 (Print), 1520-6041 (Online) (doi:https://doi.org/10.1021/om200278j)

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Abstract

1,3-Dihydro-2H-indol-2-one (1) undergoes microwave-mediated Knoevenagel condensations with 1,2,3,4,5-pentaphenylferrocene carboxaldehyde (2b) or (η4-tetraphenylcyclobutadiene)(η5-cyclopentadienylcarboxaldehyde)cobalt (2c) to afford metallocene-substituted 3-methylidene-1,3-dihydro-2H-indol-2-one 4 or 5, respectively, in excellent yields as separable E,Z-stereoisomeric mixtures. Both 4 and 5 exhibited poor kinase inhibition and no appreciable cytotoxicity toward a leukemia cell line, attributed to the steric bulk of the metallocene substituents.

Item Type: Article
Uncontrolled Keywords: metallocene, kinase inhibitor, 3-Methylidene-Oxindoles
Subjects: R Medicine > RM Therapeutics. Pharmacology
Faculty / School / Research Centre / Research Group: Faculty of Engineering & Science
Faculty of Engineering & Science > School of Science (SCI)
Related URLs:
Last Modified: 17 Oct 2016 09:11
URI: http://gala.gre.ac.uk/id/eprint/5842

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