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

doi:10.1021/om200278j

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 language	English
Pages (from-to)	3177-3181
Journal	Organometallics
Volume	30
Issue number	11
DOIs	https://doi.org/10.1021/om200278j
Publication status	Published - 2011

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@article{11c558714d2b4f05a16a660848f59cd8,

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

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.",

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

year = "2011",

doi = "10.1021/om200278j",

language = "English",

volume = "30",

pages = "3177--3181",

journal = "Organometallics",

issn = "0276-7333",

publisher = "American Chemical Society",

number = "11",

}

TY - JOUR

T1 - Size does matter

T2 - sterically demanding metallocene-substituted 3-methylidene-oxindoles exhibit poor kinase inhibitory action

AU - Spencer, John

AU - Amin, Jahangir

AU - Coxhead, Peter

AU - McGeehan, John

AU - Richards, Christopher J.

AU - Tizzard, Graham J.

AU - Coles, Simon J.

AU - Bingham, John P.

AU - Hartley, John A.

AU - Feng, Li

AU - Meggers, Eric

AU - Guille, Matt

PY - 2011

Y1 - 2011

N2 - 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.

AB - 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.

U2 - 10.1021/om200278j

DO - 10.1021/om200278j

M3 - Article

SN - 0276-7333

VL - 30

SP - 3177

EP - 3181

JO - Organometallics

JF - Organometallics

IS - 11

ER -

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

Abstract

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