The concise synthesis of chalcone, indanone and indenone analogues of combretastatin A4
- 11 February 2007
- journal article
- Published by Elsevier BV in Bioorganic & Medicinal Chemistry
- Vol. 15 (9), 3290-3298
- https://doi.org/10.1016/j.bmc.2007.02.006
Abstract
A series of aryl- and aroyl-substituted chalcone analogues of the tubulin binding agent combretastatin A4 (1) were prepared, using a recently introduced one-pot palladium-mediated hydrostannylation-coupling reaction sequence. These chalcones were converted to indanones by Nazarov cyclisation, followed by oxidation to give the corresponding indenones. Indenones were also prepared using a palladium-mediated formal [3+2]-cycloaddition process between ortho-halobenzaldehydes and diarylpropynones. All compounds were assessed as inhibitors of tubulin polymerisation, but only E-31 had activity similar to that of 1. However, compound E-31 did not exhibit antiproliferative activity against the MCF-7 cell line.Keywords
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