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.
ASJC Scopus subject areas
- Analytical Chemistry
- Molecular Medicine
- Pharmaceutical Science
- Drug Discovery
- Complementary and alternative medicine
- Organic Chemistry
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Pettit, G. R. (Creator), Quistorf, P. D. (Creator), Fry, J. A. (Creator), Herald, D. L. (Creator), Hamel, E. (Creator), Chapuis, J. (Creator) & Pettit, G. R. (Creator), The Cambridge Structural Database, 2010