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

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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 (eta(4)-tetraphenyl-cyclobutadiene)(eta(5)-cyclopentadienylcarboxaldehyd e)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-sfereoisomeric 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
Additional Information:	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 Guille, Matthew
Faculty \ School:	Faculty of Science > School of Chemistry (former - to 2024)
UEA Research Groups:	Faculty of Science > Research Groups > Synthetic Chemistry (former - to 2017) Faculty of Science > Research Groups > Chemistry of Materials and Catalysis
Depositing User:	Rachel Smith
Date Deposited:	21 Feb 2012 11:27
Last Modified:	28 Mar 2025 02:54
URI:	https://ueaeprints.uea.ac.uk/id/eprint/37270
DOI:	10.1021/om200278j

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