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:	Publisher
Last Modified:	17 Oct 2016 09:11
URI:	http://gala.gre.ac.uk/id/eprint/5842

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