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Antineoplastic agents 393. Synthesis of the trans-isomer of combretastatin A-4 prodrug

  1. Author:
    Pettit, G. R.
    Rhodes, M. R.
    Herald, D. L.
    Chaplin, D. J.
    Stratford, M. R. L.
    Hamel, E.
    Pettit, R. K.
    Chapuis, J. C.
    Oliva, D.

  2. Author Address

    Pettit RK 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 Tempe, AZ 85287 USA Mt Vernon Hosp, Canc Res Trust, Gray Lab Northwood HA6 2JR Middx England NCI, Frederick Canc Res & Dev Ctr, Lab Drug Discovery Res & Dev, Dev Therapeut Program,Div Canc Treatment & Diag Frederick, MD 21702 USA Western Oregon Univ, Dept Biol Monmouth, OR 97361 USA
    1. Year: 1998
  2. Journal: Anti-Cancer Drug Design
    1. 13
    2. 8
    3. Pages: 981-993
  4. Type of Article: Article
  1. Abstract:

    The (E)-stilbene isomer (2a) of the (Z)-combretastatin A-4 prodrug (1b) was efficiently prepared from (E)-combretastatin A-4 by a reaction sequence employing phosphorylation (dibenzyl chlorophosphite), cleavage (trimethyliodosilane) of the benzyl ester and reaction of the resulting phosphoric acid with sodium methoxide. The sodium phosphate product (2c) was also found to be an important side-product, presumably from iodine-catalyzed isomerization, when the analogous synthetic route was used to obtain the combretastatin A-4 prodrug (1b). The phosphoric acid precursor of prodrug Ib derived from (Z)-combretastatin A-4 (1a) was converted into a series of metal cation and ammonium cation salts to evaluate effects on human cancer cell growth, antimicrobial activities and solubility behavior. [References: 23]

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