Antineoplastic agents 500. Narcistatin

George Pettit, Noeleen Melody, Michael Simpson, Michael Thompson, Delbert L. Herald, John C. Knight

Research output: Contribution to journalArticle

17 Scopus citations

Abstract

An efficient procedure was found for synthetic conversion of the sparingly soluble anticancer isocarbostyril narciclasine (1), a component of various Narcissus species, to a cyclic phosphate designated narcistatin (3b). The reaction between narciclasine, tetrabutylammonium dihydrogen phosphate, and p-toluenesulfonic acid in pyridine afforded pyridinium narcistatin (3a) in reasonable yields. Transformation of narcistatin (3a) to, for example, the water-soluble prodrug sodium narcistatin (3d) was easily achieved by cation exchange chromatography. Narcistatin (3b) and 15 salt derivatives were evaluated against a panel of human cancer cell lines, and the range (0.1-0.01) of GI50 values in μg/mL was found to parallel that shown by the parent narciclasine.

Original languageEnglish (US)
Pages (from-to)92-96
Number of pages5
JournalJournal of Natural Products
Volume66
Issue number1
DOIs
StatePublished - Jan 1 2003

ASJC Scopus subject areas

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

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    Pettit, G., Melody, N., Simpson, M., Thompson, M., Herald, D. L., & Knight, J. C. (2003). Antineoplastic agents 500. Narcistatin. Journal of Natural Products, 66(1), 92-96. https://doi.org/10.1021/np020225i