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Synthesis and biological evaluation of novel paclitaxel (Taxol) D-ring modified analogues

  1. Author:
    Gunatilaka, A. A. L.
    Ramdayal, F. D.
    Sarragiotto, M. H.
    Kingston, D. G. I.
    Sackett, D. L.
    Hamel, E.

  2. Author Address

    Kingston DGI Virginia Polytech Inst & State Univ, Dept Chem Blacksburg, VA 24061 USA Virginia Polytech Inst & State Univ, Dept Chem Blacksburg, VA 24061 USA NCI, Lab Drug Discovery Res & Dev, Dev Therapeut Program,Div Canc Treatment & Diag, Fred Hutchinson Canc Res Ctr Frederick, MD 21702 USA
    1. Year: 1999
  2. Journal: Journal of Organic Chemistry
    1. 64
    2. 8
    3. Pages: 2694-2703
  4. Type of Article: Article
  1. Abstract:

    The semisynthesis and biological activity of paclitaxel (Taxol) analogues in which the oxygen atom in ring D is substituted by a sulfur or a selenium atom is presented. These derivatives were synthesized and tested in order to make more transparent the role of the oxetane ring in the biological activity of paclitaxel. The sulfur derivatives were found to be less active than paclitaxel in biological assays, while the selenium derivative could not be converted to its 4-acyl analogue. The results with the sulfur analogues suggest that the oxygen atom in the oxetane ring plays an important role in the mechanism by which paclitaxel exhibits its anticancer activity. [References: 30]

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