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. ORCID: https://orcid.org/0000-0001-7899-4082, 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:	24 Sep 2024 09:06
URI:	https://ueaeprints.uea.ac.uk/id/eprint/37270
DOI:	10.1021/om200278j

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