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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    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 languageEnglish
    Pages (from-to)219-231
    Number of pages12
    JournalOrganic and Biomolecular Chemistry
    Issue number1
    Publication statusPublished - 1 Jan 2011


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