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The synthesis and tubulin binding activity of thiophene-based analogues of combretastatin A-4

  1. Author:
    Flynn, B. L.
    Flynn, G. P.
    Hamel, E.
    Jung, M. K.

  2. Author Address

    Australian Natl Univ, Fac, Dept Chem, Canberra, ACT 0200, Australia. Australian Natl Univ, Fac, Dept Chem, Canberra, ACT 0200, Australia. NCI, Screening Technol Branch, Dev Therapeut Program, Div Canc Treatment & Diagnosis, NIH, Ft Detrick, MD 21702 USA. NCI, Sci Applicat Int Corp, NIH, Frederick, MD 21701 USA. Flynn BL Australian Natl Univ, Fac, Dept Chem, Canberra, ACT 0200, Australia.
    1. Year: 2001
  2. Journal: Bioorganic & Medicinal Chemistry Letters
    1. 11
    2. 17
    3. Pages: 2341-2343
  4. Type of Article: Article
  1. Abstract:

    A number of analogues of combretastatin A-4 (1), containing a thiophene ring interposed between the two phenyl groups, have been prepared. The synthesis of these compounds employed. a combination of palladium-mediated coupling and iodocyclization techniques. The thiophene compounds 11, 14, 18, and 19 also represent non-benzofused analogues of some recently described tubulin binding benzo[b]thiophenes 3 5. The most active thiophene compounds identified in this study were 11, 14, and 18. Overall they are less active than I but exhibit comparable activity to the most active of the benzo[b]thiophenes 3 5. A structure-activity relationship or these compounds is considered. (C) 2001 Elsevier Science Ltd. All rights reserved.

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