Synthesis and biological activity of 4′-C-hydroxymethyl-2′-fluoro-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-α-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 (16β) showed slight cytotoxicity in CCRF-CEM leukemia cells.
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    Digital Object Identifier (doi)

    Author List

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

  • 1583
  • End Page

  • 1598
  • Volume

  • 20
  • Issue

  • 8