Synthesis and biological activity of 4'-C-hydroxymethyl-2'-fluro-D-arabinofuranosylpurine nucleosides.

Academic Article

Abstract

  • A series of 4'-C-hydroxymethyl-2'-fluoro-D-arabinofuranosylpurine nucleosides was prepared and evaluated for cytotoxicity. The details of a convenient synthesis of the carbohydrate precursor 4-C-hydroxymethyl-3,5-di-O-benzoyl-2-fluoro-alpha-D-arabinofuranosyl bromide (13) are presented. Proof of the structure and configuration at all chiral centers of the sugars and the nucleosides were obtained by proton NMR. All five target nucleosides were evaluated for cytotoxicity in human tumor cell lines. The 4'-C-hydroxymethyl clofarabine analogue (16beta) showed slight cytotoxicity in CCRF-CEM leukemia cells.
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    Keywords

  • Anticarcinogenic Agents, Arabinonucleosides, Cell Survival, Chromatography, High Pressure Liquid, Chromatography, Thin Layer, Humans, Magnetic Resonance Spectroscopy, Mass Spectrometry, Spectrophotometry, Ultraviolet, Structure-Activity Relationship, Tumor Cells, Cultured
  • Digital Object Identifier (doi)

    Authorlist

  • Shortnacy-Fowler AT; Tiwari KN; Montgomery JA; Secrist JA
  • Start Page

  • 1583
  • End Page

  • 1598
  • Volume

  • 20
  • Issue

  • 8