Antineoplastic agents 500. Narcistatin

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

doi:10.1021/np020225i

Antineoplastic agents 500. Narcistatin

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

Molecular Sciences, School of (SMS)

Research output: Contribution to journal › Article › peer-review

19 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 language	English (US)
Pages (from-to)	92-96
Number of pages	5
Journal	Journal of Natural Products
Volume	66
Issue number	1
DOIs	https://doi.org/10.1021/np020225i
State	Published - 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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AU - Pettit, George

AU - Melody, Noeleen

AU - Simpson, Michael

AU - Thompson, Michael

AU - Herald, Delbert L.

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N2 - 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.

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Antineoplastic agents 500. Narcistatin

Abstract

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