Tubulin-binding dibenz[c,e]oxepines as colchinol analogues for targeting tumour vasculature

David J. Edwards; John A. Hadfield; Timothy W. Wallace; Sylvie Ducki

doi:10.1039/c0ob00500b

Tubulin-binding dibenz[c,e]oxepines as colchinol analogues for targeting tumour vasculature

David J. Edwards, John A. Hadfield, Timothy W. Wallace, Sylvie Ducki

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Abstract

Various methoxy- and hydroxy-substituted dibenz[c,e]oxepines were prepared via the copper(i)-induced coupling of ether-tethered arylstannanes or the dehydrative cyclisation of 1,1′-biphenyl-2,2′-dimethanols, assembled using the Ullmann cross-coupling of ortho-bromoaryl carbonyl compounds. The dibenzoxepines were screened for their ability to inhibit tubulin polymerisation and the in vitro growth of K562 human chronic myelogenous leukemia cells. The most active was 5,7-dihydro-3,9,10,11-tetramethoxydibenz[c,e]oxepin-4-ol, whose tubulin inhibitory and cytotoxicity (IC50) values were 1 μM and 40 nM, respectively. © 2011 The Royal Society of Chemistry.

Original language	English
Pages (from-to)	219-231
Number of pages	12
Journal	Organic and Biomolecular Chemistry
Volume	9
Issue number	1
DOIs	https://doi.org/10.1039/c0ob00500b
Publication status	Published - 1 Jan 2011

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Tubulin-binding dibenz[c,e]oxepines: Part 2. Structural variation and biological evaluation as tumour vasculature disrupting agents
Rossington, S., Hadfield, J., Shnyder, S. D., Wallace, T. & Williams, K., 1 Mar 2017, In: Bioorganic and Medicinal Chemistry. 25, 5, p. 1630-1642 13 p.
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title = "Tubulin-binding dibenz[c,e]oxepines as colchinol analogues for targeting tumour vasculature",

abstract = "Various methoxy- and hydroxy-substituted dibenz[c,e]oxepines were prepared via the copper(i)-induced coupling of ether-tethered arylstannanes or the dehydrative cyclisation of 1,1′-biphenyl-2,2′-dimethanols, assembled using the Ullmann cross-coupling of ortho-bromoaryl carbonyl compounds. The dibenzoxepines were screened for their ability to inhibit tubulin polymerisation and the in vitro growth of K562 human chronic myelogenous leukemia cells. The most active was 5,7-dihydro-3,9,10,11-tetramethoxydibenz[c,e]oxepin-4-ol, whose tubulin inhibitory and cytotoxicity (IC50) values were 1 μM and 40 nM, respectively. {\textcopyright} 2011 The Royal Society of Chemistry.",

author = "Edwards, {David J.} and Hadfield, {John A.} and Wallace, {Timothy W.} and Sylvie Ducki",

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AU - Edwards, David J.

AU - Hadfield, John A.

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N2 - Various methoxy- and hydroxy-substituted dibenz[c,e]oxepines were prepared via the copper(i)-induced coupling of ether-tethered arylstannanes or the dehydrative cyclisation of 1,1′-biphenyl-2,2′-dimethanols, assembled using the Ullmann cross-coupling of ortho-bromoaryl carbonyl compounds. The dibenzoxepines were screened for their ability to inhibit tubulin polymerisation and the in vitro growth of K562 human chronic myelogenous leukemia cells. The most active was 5,7-dihydro-3,9,10,11-tetramethoxydibenz[c,e]oxepin-4-ol, whose tubulin inhibitory and cytotoxicity (IC50) values were 1 μM and 40 nM, respectively. © 2011 The Royal Society of Chemistry.

AB - Various methoxy- and hydroxy-substituted dibenz[c,e]oxepines were prepared via the copper(i)-induced coupling of ether-tethered arylstannanes or the dehydrative cyclisation of 1,1′-biphenyl-2,2′-dimethanols, assembled using the Ullmann cross-coupling of ortho-bromoaryl carbonyl compounds. The dibenzoxepines were screened for their ability to inhibit tubulin polymerisation and the in vitro growth of K562 human chronic myelogenous leukemia cells. The most active was 5,7-dihydro-3,9,10,11-tetramethoxydibenz[c,e]oxepin-4-ol, whose tubulin inhibitory and cytotoxicity (IC50) values were 1 μM and 40 nM, respectively. © 2011 The Royal Society of Chemistry.

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JF - Organic & biomolecular chemistry

SN - 1477-0520

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Tubulin-binding dibenz[c,e]oxepines as colchinol analogues for targeting tumour vasculature

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Tubulin-binding dibenz[c,e]oxepines: Part 2. Structural variation and biological evaluation as tumour vasculature disrupting agents

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