Antineoplastic Agents. 527. Synthesis of 7-Deoxynarcistatin, 7-Deoxy-trans-dihydronarcistatin, and trans-Dihydronarcistatin 1

Antineoplastic Agents. 527. Synthesis of 7-Deoxynarcistatin, 7-Deoxy-trans-dihydronarcistatin, and trans-Dihydronarcistatin 1

The synthesis of sodium narcistatin (8) was improved (88% overall yield) and the modified reaction sequence was utilized to synthesize three new 3,4-cyclic phosphate prodrugs, sodium 7-deoxynarcistatin (5), sodium 7-deoxy-trans-dihydronarcistatin (6), and sodium trans-dihydronarcistatin (7). The hum...

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Veröffentlicht in:Journal of natural products (Washington, D.C.) D.C.), 2005-02, Vol.68 (2), p.207-211
Hauptverfasser: Pettit, George R, Melody, Noeleen
Format: Artikel
Sprache:eng
Schlagworte:
7-deoxy-trans-dihydronarcistatin
7-deoxynarcistatin
Amaryllidaceae Alkaloids - chemistry
Amaryllidaceae Alkaloids - pharmacology
antineoplastic agents
Antineoplastic Agents, Phytogenic - chemical synthesis
Antineoplastic Agents, Phytogenic - pharmacology
Cell Line, Tumor
chemical structure
Drug Screening Assays, Antitumor
Heterocyclic Compounds, 4 or More Rings - chemical synthesis
Humans
Hymenocallis
Hymenocallis littoralis
Liliaceae - chemistry
Molecular Structure
narcistatins
organophosphorus compounds
Pancratium
Pancratium littorale
Phenanthridines - chemistry
Phenanthridines - pharmacology
phytochemicals
Plants, Medicinal - chemistry
trans-dihydronarcistatin
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Zusammenfassung:The synthesis of sodium narcistatin (8) was improved (88% overall yield) and the modified reaction sequence was utilized to synthesize three new 3,4-cyclic phosphate prodrugs, sodium 7-deoxynarcistatin (5), sodium 7-deoxy-trans-dihydronarcistatin (6), and sodium trans-dihydronarcistatin (7). The human cancer cell line inhibitory isocarbostyril precursors were isolated from the bulbs of Hymenocallis littoralis obtained by horticultural production or reduction of narciclasine (1a → 4) from the same source.
ISSN:0163-3864
1520-6025
DOI:10.1021/np0304518