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The concise synthesis of chalcone, indanone and indenone analogues of combretastatin A4

  1. Author:
    Kerr, D. J.
    Hamel, E.
    Jung, M. K.
    Flynn, B. L.

  2. Author Address

    Monash Univ, Fac Pharm, Dept Med Chem, Parkville, Vic 3052, Australia. NCI, Toxicol & Pharmacol Branch, Dev Therapeut Program, Div Canc Treatment & Diagnosis, Ft Detrick, MD 21702 USA. NCI, SAIC Frederick, NIH, Frederick, MD 21702 USA.;Flynn, BL, Monash Univ, Fac Pharm, Dept Med Chem, 381 Royal Pde, Parkville, Vic 3052, Australia.;b.flynn@iliad.com.au
    1. Year: 2007
    2. Date: May
  2. Journal: Bioorganic & Medicinal Chemistry
    1. 15
    2. 9
    3. Pages: 3290-3298
  4. Type of Article: Article
  5. ISSN: 0968-0896
  1. 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. (c) 2007 Elsevier Ltd. All rights reserved.

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External Sources

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  2. DOI: 10.1016/j.bmc.2007.02.006
  3. View record in Web of Science®
  4. WOS: 000246002800020

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