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Antineoplastic agents. 487. Synthesis and biological evaluation of the antineoplastic agent 3,4-methylenedioxy-5,4 '-dimethoxy- 3 '-amino-Z-stilbene and derived amino acid amides

  1. Author:
    Pettit, G. R.
    Anderson, C. R.
    Herald, D. L.
    Jung, M. K.
    Lee, D. J.
    Hamel, E.
    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, Frederick Canc Res & Dev Ctr, Sci Applicat Int Corp, NIH, Frederick, MD 21702 USA NCI, Div Canc Treatment & Diag, Dev Therapeut Program, Screening Technol Branch,NIH, Frederick, MD 21702 USA Pettit GR Arizona State Univ, Canc Res Inst, POB 872404, Tempe, AZ 85287 USA
    1. Year: 2003
  2. Journal: Journal of Medicinal Chemistry
    1. 46
    2. 4
    3. Pages: 525-531
  4. Type of Article: Article
  1. Abstract:

    An efficient synthesis of 3,4-methylenedioxy-5,4'-dimethoxy-3'- amino-Z-stilbene (1c) and hydrochloride (1d) is reported. The nitrostilbene intermediate 6a was obtained via a Wittig reaction using phosphonium salt 4 and 3-nitro-4- methoxybenzaldehyde 5. A one-step reduction using zinc in acetic acid produced the synthetic objective amine 1c. The coupling of this amine with various Fmoc amino acids, followed by cleavage of the a-amine protecting group, resulted in a series of new cancer cell growth inhibitory amides. Amine 1c, hydrochloride 1d, glycine amide 3b, and tyrosine amide 3f had the highest level (GI(50) = 10(-2)-10(-3) mug/mL) of activity against a panel of six human and one animal (P388) cancer cell lines. Amine 1c and its hydrochloride 1d, potently inhibited tubulin polymerization by binding at the colchicine site, while the amides had little activity against purified tubulin. Nevertheless, most of the amides caused a marked increase in the mitotic index of treated cells, indicating that tubulin was their intracellular target.

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