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Antineoplastic Agents. 565. Synthesis of Combretastatin D-2 Phosphate and Dihydro-combretastatin D-2

  1. Author:
    Pettit, G. R.
    Quistorf, P. D.
    Fry, J. A.
    Herald, D. L.
    Hamel, E.
    Chapuis, J. C.

  2. Author Address

    Pettit, George R.; Quistorf, Peter D.; Fry, Jeremy A.; Herald, Delbert L.; Chapuis, Jean-Charles] Arizona State Univ, Canc Res Inst, Tempe, AZ 85287 USA. Arizona State Univ, Dept Chem & Biochem, Tempe, AZ 85287 USA. [Hamel, Ernest] NCI, DTP, DCTC, Frederick, MD 21702 USA.
    1. Year: 2009
  2. Journal: Journal of Natural Products
    1. 72
    2. 5
    3. Pages: 876-883
  4. Type of Article: Article
  1. Abstract:

    A modified synthetic route to combretastatin D-2 (5) was devised in order to further evaluate its biological activity, for its conversion to phosphate prodrugs (25-28), and as a route to obtaining dihydro-combretastatin D-2 (42). A parallel first total synthesis of dihydro-combretastatin D-2 was completed, proceeding from a saturated 3-phenylpropionic ester intermediate via the Ullmann biaryl ether reaction (39-41). In contrast to the cancer cell growth inhibitory activity exhibited by combretastatin D-2, relatively minor structural modifications (41, 42) caused elimination of those properties.

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  2. DOI: 10.1021/np800635h
  3. PMID: 19226154

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