Antineoplastic agents. 527. Synthesis of 7-deoxynarcistatin, 7-deoxy-trans-dihydronarcistatin, and trans-dihydronarcistatin 1(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 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.
Pettit
George R
GR
Cancer Research Institute, Department of Chemistry and Biochemistry, Arizona State University, Tempe, AZ 85287-2404, USA.
Melody
Noeleen
N
D047151:Amaryllidaceae Alkaloids / Q000737:chemistry / Q000494:pharmacology; D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000494:pharmacology; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D006801:Humans; D019668:Liliaceae / Q000737:chemistry; D015394:Molecular Structure; D010617:Phenanthridines / Q000737:chemistry / Q000494:pharmacology; D010946:Plants, Medicinal / Q000737:chemistry
C498492:7-deoxy-trans-dihydronarcistatin; C498491:7-deoxynarcistatin; D047151:Amaryllidaceae Alkaloids; D000972:Antineoplastic Agents, Phytogenic; D006576:Heterocyclic Compounds, 4 or More Rings; D010617:Phenanthridines; C498494:trans-dihydronarcistatin; C010753:narciclasine