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

journal contribution
posted on 2023-06-08, 12:40 authored by John SpencerJohn Spencer, Jahangir Amin, Peter Coxhead, John McGeehan, Christopher Richards, Graham Tizzard, Simon Coles, John Bingham, John Hartley, Li Feng, Eric Meggers, Matthew Guille
1,3-Dihydro-2H-indol-2-one (1) undergoes microwave-mediated Knoevenagel condensations with 1,2,3,4,5- pentaphenylferrocene carboxaldehyde (2b) or (? 4 -tetraphenylcyclobutadiene)(? 5 -cyclopentadienylcarboxaldehyde)cobalt (2c) to a?ord 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.

History

Publication status

  • Published

Journal

Organometallics

ISSN

0276-7333

Publisher

American Chemical Society

Issue

11

Volume

30

Page range

3177-3181

Department affiliated with

  • Chemistry Publications

Full text available

  • No

Peer reviewed?

  • Yes

Legacy Posted Date

2012-10-22

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