Size does matter. Sterically demanding metallocene-substituted 3-methylidene-oxindoles exhibit poor kinase inhibitory action
Size does matter. Sterically demanding metallocene-substituted 3-methylidene-oxindoles exhibit poor kinase inhibitory action
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)-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-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.
3177-3181
Spencer, John
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Amin, Jahangir
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Coxhead, Peter
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McGeehan, John
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Richards, Christopher J.
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Tizzard, Graham J.
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Coles, Simon J.
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Bingham, John P.
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Hartley, John A.
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Feng, Li
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Meggers, Eric
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Guille, Matthew
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June 2011
Spencer, John
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Amin, Jahangir
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Coxhead, Peter
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McGeehan, John
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Richards, Christopher J.
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Tizzard, Graham J.
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Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Bingham, John P.
e41604b8-44ec-4705-8c25-00bd5bc11827
Hartley, John A.
17407879-36ee-462f-bb21-4e912619cfa0
Feng, Li
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Meggers, Eric
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Guille, Matthew
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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), .
(doi:10.1021/om200278j).
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)-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-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.
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e-pub ahead of print date: 11 May 2011
Published date: June 2011
Organisations:
Organic Chemistry: Synthesis, Catalysis and Flow
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Local EPrints ID: 346141
URI: http://eprints.soton.ac.uk/id/eprint/346141
ISSN: 0276-7333
PURE UUID: ce65f24e-2f39-477f-967c-963d7e2b7796
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Date deposited: 14 Jan 2013 14:10
Last modified: 15 Mar 2024 03:10
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Author:
John Spencer
Author:
Jahangir Amin
Author:
Peter Coxhead
Author:
John McGeehan
Author:
Christopher J. Richards
Author:
John P. Bingham
Author:
John A. Hartley
Author:
Li Feng
Author:
Eric Meggers
Author:
Matthew Guille
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