Size does matter: sterically demanding metallocene-substituted 3-methylidene-oxindoles exhibit poor kinase inhibitory action

John Spencer, Jahangir Amin, Peter Coxhead, John McGeehan, Christopher J. Richards, Graham J. Tizzard, Simon J. Coles, John P. Bingham, John A. Hartley, Li Feng, Eric Meggers, Matt Guille

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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.
Original languageEnglish
Pages (from-to)3177-3181
JournalOrganometallics
Volume30
Issue number11
DOIs
Publication statusPublished - 2011

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