A one-pot synthesis of 1-alpha- and 1-beta-D-arabinofuranosyl-2-nitroimidazoles: synthons to the markers of tumor hypoxia.
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.
Naimi
Ebrahim
E
Department of Oncologic Imaging, Cross Cancer Institute and Faculty of Pharmacy and Pharmaceutical Sciences, University of Alberta, Edmonton, Canada.
Kumar
Piyush
P
McEwan
Alexander J B
AJ
Wiebe
Leonard I
LI
D014408:Biomarkers, Tumor; D015687:Cell Hypoxia; D015394:Molecular Structure; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D009369:Neoplasms / Q000473:pathology*; D009593:Nitroimidazoles / Q000138:chemical synthesis* / Q000737:chemistry
C513638:1-beta-D-arabinofuranosyl-2-nitroimidazole; D014408:Biomarkers, Tumor; D009005:Monosaccharides; D009593:Nitroimidazoles; C070588:iodoazomycin arabinoside