Synthesis of phenstatin and prodrugs thereof

Details Synthesis of phenstatin and prodrugs thereof Synthesis of phenstatin and prodrugs thereof

2005-09-13

2005-09-13

Barts, Samuel (Department: 1621)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Radical -xh acid, or anhydride, acid halide or salt thereof...

C514S546000, C514S679000, C560S140000, C562S024000, C568S333000

Reexamination Certificate

active

06943194

ABSTRACT:
A newly discovered antineoplastic compound denominated “phenstatin” is herein described as are synthetic methods for producing phenstatin and the active prodrug thereof. Phenstatin was converted to the sodium phosphate prodrug (3d) by a dibenzylphosphite phosphorylation and subsequent hydrogenolysis sequence 3b→3c→3d. Phenstatin (3b) was found to be a potent inhibitor of tubulin polymerization and the binding of colchicine to tubulin comparable to combretastatin A-4 (1b).

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Pettit, G. R. et al.; “Antineoplastic agents. 379. Synthesis of Phenstatin Phosphate.”, Journal of Medicinal Chemistry, vol. 41, No. 10, pp. 1688-1695 (May 7, 1998).
Gschwend, Daniel A. et al., “Specificity in Structure-Based Drug Design: Identification of a Novel, Selective Inhibitor ofPneumocystis cariniiDihydrofolate Reductase,” PROTEINS: Structure, Function, and Genetics, vol. 29, No. 1, pp. 59-67 (1997).

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