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Antineoplastic agents 463. Synthesis of combretastatin A-3 diphosphate prodrugs

  1. Author:
    Pettit, G. R.
    Minardi, M. D.
    Boyd, M. R.
    Pettit, R. K.

  2. Author Address

    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. Pettit RK Arizona State Univ, Canc Res Inst, POB 872404, Tempe, AZ 85287 USA.
    1. Year: 2000
  2. Journal: Anti-Cancer Drug Design
    1. 15
    2. 6
    3. Pages: 397-403
  4. Type of Article: Article
  1. Abstract:

    A new and more efficient synthesis of combretastatin A-3 (2a) was completed (8.4% overall yield) starting from methyl gallate and isovanillin with aldehyde 5 and phosphonium salt 8 as key intermediates. Conversion of combretastatin A-3 (2a) to a series of diphosphate prodrugs (10a-1) was readily achieved. Both the diphosphate sodium (10a) and potassium salts (10c) displayed aqueous solubility in excess of 220 mg/ml at room temperature and good cancer cell line inhibitory activity.

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