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Antineoplastic agents 460. Synthesis of combretastatin A-2 prodrugs

  1. Author:
    Pettit, G. R.
    Moser, B. R.
    Boyd, M. R.
    Schmidt, J. M.
    Pettit, R. K.
    Chapuis, J. C.

  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, Ft Detrick, MD 21702 USA Pettit GR Arizona State Univ, Canc Res Inst, POB 872404, Tempe, AZ 85287 USA
    1. Year: 2001
  2. Journal: Anti-Cancer Drug Design
    1. 16
    2. 4-5
    3. Pages: 185-193
  4. Type of Article: Article
  1. Abstract:

    The original synthesis of combretastatin A-2 (1a) was modified to provide an efficient scale-up procedure for obtaining this antineoplastic stilbene. Subsequent conversion to a useful prodrug was accomplished by phosphorylation employing in situ formation of dibenzylchlorophosphite followed by cleavage of the benzyl ester protective groups with bromotrimethylsilane to afford the phosphoric acid intermediate 11. The latter was immediately treated with sodium methoxide to complete a practical route to the disodium phosphate prodrug (2a). The phosphoric acid precursor (11) of phosphate 2a was employed in a parallel series of reactions to produce a selection of metal and ammonium cation prodrug candidates. Each of the phosphate salts (2a-q) was evaluated with respect to relative solubility behavior, cancer cell growth inhibition and antimicrobial activity.

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