Antineoplastic agents. 527. Synthesis of 7-deoxynarcistatin, 7-deoxy-trans-dihydronarcistatin, and trans-dihydronarcistatin 1

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Abstract

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.

Original languageEnglish (US)
Pages (from-to)207-211
Number of pages5
JournalJournal of Natural Products
Volume68
Issue number2
DOIs
StatePublished - Feb 2005

Fingerprint

antineoplastic agents
Antineoplastic Agents
Sodium
sodium
synthesis
Hymenocallis
Prodrugs
bulbs
Cell Line
Phosphates
Cells
cell lines
phosphates
7-deoxy-trans-dihydronarcistatin
7-deoxynarcistatin
trans-dihydronarcistatin
Neoplasms

ASJC Scopus subject areas

  • Plant Science
  • Chemistry (miscellaneous)
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

Cite this

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title = "Antineoplastic agents. 527. Synthesis of 7-deoxynarcistatin, 7-deoxy-trans-dihydronarcistatin, and trans-dihydronarcistatin 1",
abstract = "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.",
author = "George Pettit and Noeleen Melody",
year = "2005",
month = "2",
doi = "10.1021/np0304518",
language = "English (US)",
volume = "68",
pages = "207--211",
journal = "Journal of Natural Products",
issn = "0163-3864",
publisher = "American Chemical Society",
number = "2",

}

TY - JOUR

T1 - Antineoplastic agents. 527. Synthesis of 7-deoxynarcistatin, 7-deoxy-trans-dihydronarcistatin, and trans-dihydronarcistatin 1

AU - Pettit, George

AU - Melody, Noeleen

PY - 2005/2

Y1 - 2005/2

N2 - 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.

AB - 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.

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U2 - 10.1021/np0304518

DO - 10.1021/np0304518

M3 - Article

VL - 68

SP - 207

EP - 211

JO - Journal of Natural Products

JF - Journal of Natural Products

SN - 0163-3864

IS - 2

ER -