Antineoplastic agents 500. Narcistatin.

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 GI(50) values in micro g/mL was found to parallel that shown by the parent narciclasine.
Authors	George R Pettit, Noeleen Melody, Michael Simpson, Michael Thompson, Delbert L Herald, John C Knight
Journal	Journal of natural products (J Nat Prod) Vol. 66 Issue 1 Pg. 92-6 (Jan 2003) ISSN: 0163-3864 [Print] United States
PMID	12542352 (Publication Type: Comparative Study, Journal Article, Research Support, Non-U.S. Gov't, Research Support, U.S. Gov't, Non-P.H.S., Research Support, U.S. Gov't, P.H.S.)
Chemical References	Alkaloids Amaryllidaceae Alkaloids Antineoplastic Agents, Phytogenic Heterocyclic Compounds, 4 or More Rings Organophosphates Organophosphorus Compounds Phenanthridines Prodrugs Quaternary Ammonium Compounds narcistatin narciclasine
Topics	Alkaloids (chemistry) Amaryllidaceae Alkaloids Animals Antineoplastic Agents, Phytogenic (chemical synthesis, pharmacology) Cell Division (drug effects) Crystallography, X-Ray Drug Screening Assays, Antitumor Heterocyclic Compounds, 4 or More Rings (chemical synthesis, pharmacology) Humans Leukemia P388 Mice Molecular Conformation Molecular Structure Narcissus (chemistry) Organophosphates (chemical synthesis, pharmacology) Organophosphorus Compounds (chemical synthesis, pharmacology) Phenanthridines Plants, Medicinal (chemistry) Prodrugs (chemical synthesis, pharmacology) Quaternary Ammonium Compounds (chemical synthesis, pharmacology) Tumor Cells, Cultured (drug effects)

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