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Antineoplastic agents. 443. Synthesis of the cancer cell growth inhibitor hydroxyphenstatin and its sodium diphosphate prodrug

  1. Author:
    Pettit, G. R.
    Grealish, M. P.
    Herald, D. L.
    Boyd, M. R.
    Hamel, E.
    Pettit, R. K.

  2. Author Address

    Pettit GR Arizona State Univ, Canc Res Inst POB 872404 Tempe, AZ 85287 USA Arizona State Univ, Canc Res Inst Tempe, AZ 85287 USA Arizona State Univ, Dept Chem & Biochem Tempe, AZ 85287 USA NCI, Lab Drug Discovery Res & Dev, DTP, DCTD,Frederick Canc Res & Dev Ctr Frederick, MD 21702 USA NCI, Screening Technol Branch, DTP, DCTD,Frederick Canc Res & Dev Ctr Frederick, MD 21702 USA
    1. Year: 2000
  2. Journal: Journal of Medicinal Chemistry
    1. 43
    2. 14
    3. Pages: 2731-2737
  4. Type of Article: Article
  1. Abstract:

    A structure-activity relationship (SAR) study of the South African willow tree (Combretum caffrum) antineoplastic constituent combretastatin A-4 (3b) led to the discovery of a potent cancer cell growth inhibitor designated phenstatin (5a). This benzophenone derivative of combretastatin A-4 showed remarkable antineoplastic activity, and the benzophenone derivative of combretastatin A-1 was therefore synthesized. The benzophenone, designated hydroxyphenstatin (6a), was synthesized by coupling of a protected bromobenzene and a benzaldehyde to give the benzhydrol with subsequent oxidation to the ketone. Hydroxyphenstatin was converted to the sodium phosphate prodrug (6e) by a dibenzyl phosphite phosphorylation and subsequent benzyl cleavage (6a --> 6d --> 6e). While hydroxyphenstatin (6a) was a potent inhibitor of tubulin polymerization with activity comparable to that of combretastatin A-1 (3a), the phosphorylated derivative (6e) was inactive. [References: 32]

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