A one-pot synthesis of 1-alpha- and 1-beta-D-arabinofuranosyl-2-nitroimidazoles: synthons to the markers of tumor hypoxia

Nucleosides Nucleotides Nucleic Acids. 2005;24(3):173-8. doi: 10.1081/NCN-55700.

Abstract

1-alpha- and 1-beta-D-Arabinofuranosyl-2-nitroimidazole (alpha-AZA and beta-AZ A) are synthons for a number of potential markers of tissue hypoxia. A one pot synthesis in which 2-nitroimidazole is coupled with a mixture of alpha- and beta-1-O-acetyl-2,3,5-tri-O-benzoyl-D-arabinofuranose in the presence of stannic chloride, followed by deprotection using ammonia/methanol, is described Previously reported conditions for coupling 2-nitroimidazole to 1-alpha-bromoarabinofuranose protected by base-hydrolyzable groups afforded alpha-AZA almost exclusively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biomarkers, Tumor*
  • Cell Hypoxia*
  • Molecular Structure
  • Monosaccharides / chemical synthesis*
  • Monosaccharides / chemistry
  • Neoplasms / pathology*
  • Nitroimidazoles / chemical synthesis*
  • Nitroimidazoles / chemistry

Substances

  • 1-beta-D-arabinofuranosyl-2-nitroimidazole
  • Biomarkers, Tumor
  • Monosaccharides
  • Nitroimidazoles
  • iodoazomycin arabinoside