Synthesis of 1-beta-D-(5-deoxy-5-iodoarabinofuranosyl)-2-nitroimidazole (beta-IAZA): a novel marker of tissue hypoxia.
The present work describes the synthesis of the beta-isomer of 1-alpha-D-(5-deoxy-5-iodoarabinofuranosyl)-2-nitroimidazole (IAZA). Radioiodinated IAZA ((123)I-IAZA) has been extensively studied as a radiopharmaceutical for the diagnosis of regional and/or focal tissue hypoxia in a variety of clinical pathologies. The beta-anomer of IAZA, 1-beta-D-(5-deoxy-5-iodoarabinofuranosyl)-2-nitroimidazole (beta-IAZA, 1), was synthesized via an unconventional route starting from 1-beta-D-(ribofuranosyl)-2-nitroimidazole (AZR), with a change of configuration at the C-2'-position to afford 1-beta-D-(arabinofuranosyl)-2-nitroimidazole (beta-AZA, 7). Nucleophilic iodination of the 5'-O-toluenesulfonyl-2',3'-di-O-acetyl precursor of beta-AZA, 9, followed by deprotection, afforded 1 in satisfactory yield. beta-IAZA (1) was also synthesized from 7 using molecular iodine and triphenylphosphine.
Kumar
Piyush
P
Faculty of Pharmacy & Pharmaceutical Sciences, University of Alberta, Edmonton, Canada.
Ohkura
Kazue
K
Beiki
Davood
D
Wiebe
Leonard Irving
LI
Seki
Koh-ichi
K
D015415:Biomarkers / Q000737:chemistry; D015687:Cell Hypoxia / Q000502:physiology; D009593:Nitroimidazoles / Q000138:chemical synthesis*; D013237:Stereoisomerism
D015415:Biomarkers; D009593:Nitroimidazoles; C070588:iodoazomycin arabinoside