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

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.

• Authors: Ebrahim Naimi, Piyush Kumar, Alexander J B McEwan, Leonard I Wiebe
• Journal: Nucleosides, nucleotides & nucleic acids (Nucleosides Nucleotides Nucleic Acids) Vol. 24 Issue 3 Pg. 173-8 ( 2005) ISSN: 1525-7770 [Print] United States
• PMID: 15892256 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

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

Topics

• Biomarkers, Tumor
• Cell Hypoxia
• Molecular Structure
• Monosaccharides (chemical synthesis, chemistry)
• Neoplasms (pathology)
• Nitroimidazoles (chemical synthesis, chemistry)