2. Academic Validation
  3. Antineoplastic agents. 565. Synthesis of combretastatin D-2 phosphate and dihydro-combretastatin D-2

Antineoplastic agents. 565. Synthesis of combretastatin D-2 phosphate and dihydro-combretastatin D-2

  • J Nat Prod. 2009 May 22;72(5):876-83. doi: 10.1021/np800635h.
George R Pettit 1,  Peter D Quistorf,  Jeremy A Fry,  Delbert L Herald,  Ernest Hamel,  Jean-Charles Chapuis
Affiliations

Affiliation

  • 1 Department of Chemistry and Biochemistry, Cancer Research Institute, Arizona State University, PO Box 871604, Tempe, Arizona 85287-1604, USA. [email protected]
PMID: 20161135 DOI: 10.1021/np800635h
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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