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

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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.

Bibliographical metadata

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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