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

George Pettit, Peter D. Quistorf, Jeremy A. Fry, Delbert L. Herald, Ernest Hamel, Jean Chapuis

Research output: Contribution to journalArticle

17 Citations (Scopus)

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.

Original languageEnglish (US)
Pages (from-to)876-883
Number of pages8
JournalJournal of Natural Products
Volume72
Issue number5
DOIs
StatePublished - May 22 2009

Fingerprint

Antineoplastic Agents
Phosphates
Prodrugs
Cell growth
Bioactivity
Ether
Esters
combretastatin
Growth
Neoplasms

ASJC Scopus subject areas

  • Complementary and alternative medicine
  • Molecular Medicine
  • Organic Chemistry
  • Analytical Chemistry
  • Pharmaceutical Science
  • Pharmacology
  • Drug Discovery

Cite this

Antineoplastic agents. 565. Synthesis of combretastatin D-2 phosphate and dihydro-combretastatin D-2. / Pettit, George; Quistorf, Peter D.; Fry, Jeremy A.; Herald, Delbert L.; Hamel, Ernest; Chapuis, Jean.

In: Journal of Natural Products, Vol. 72, No. 5, 22.05.2009, p. 876-883.

Research output: Contribution to journalArticle

Pettit, George ; Quistorf, Peter D. ; Fry, Jeremy A. ; Herald, Delbert L. ; Hamel, Ernest ; Chapuis, Jean. / Antineoplastic agents. 565. Synthesis of combretastatin D-2 phosphate and dihydro-combretastatin D-2. In: Journal of Natural Products. 2009 ; Vol. 72, No. 5. pp. 876-883.
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