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Antineoplastic agents 442. Synthesis and biological activities of dioxostatin

  1. Author:
    Pettit, G. R.
    Lippert, J. W.
    Boyd, M. R.
    Verdier-Pinard, P.
    Hamel, E.

  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, Frederick Canc Res & Dev Ctr, Lab Drug Discovery Res, Frederick, MD 21702 USA. NCI, Frederick Canc Res & Dev Ctr, Dev & Screening Technol Branch, DTP DCTD, Frederick, MD 21702 USA. Pettit GR Arizona State Univ, Canc Res Inst, POB 872404, Tempe, AZ 85287 USA.
    1. Year: 2000
  2. Journal: Anti-Cancer Drug Design
    1. 15
    2. 5
    3. Pages: 361-371
  4. Type of Article: Article
  1. Abstract:

    A high-yield regioselective synthesis of (E)-combretastatin A-1 2b was completed using methoxymethyl (MOM) protection and a Wadsworth-Emmons reaction as key steps. In turn, (E)-stilbene 11 was converted by convenient syntheses to both (S,S)- and (R,R)-1,3-dioxolanes 5a and 6a. A Sharpless asymmetric dihydroxylation reaction was employed for preparation of intermediates (S,S)-12 and (R,R)-13. The (4S,5S)-4-(2 ' ,3 ' dihydroxy-4 ' -methoxyphenyl)-5-(3 " ,4 " ,5 " - trimethoxyphenyl)-1, 3-dioxolane 5a was found to be a highly potent inhibitor of microtubule assembly (IC50 = 0.59 muM) and was designated dioxostatin. Conversion to sodium phosphate 17 (P388 lymphocytic leukemia cell line: ED50 = 0.2 mug/ml) provided a very useful water-soluble prodrug.

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