Tehran University of Medical Sciences
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Davood Beiki

Synthesis of 1-b-D-(5-deoxy-5-iodoarabinofuranosyl)-2-nitroimidazole (b-IAZA): a novel marker of tissue hypoxia

Authors: Kumar P, Ohkura K, Beiki D, Wiebe LI, Seki KI,
Chem Pharm Bull, Vol.51, No.4, 2003,Page:399-403

The present work describes the synthesis of the b -isomer of 1-a-D-(5-deoxy-5-iodoarabinofuranosyl)-2-nitroimidazole (IAZA). Radioiodinated IAZA (123I-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 b -anomer of IAZA, 1-b -D-(5-deoxy-5-iodoarabinofuranosyl)-2-nitroimidazole (b -IAZA, 1), was synthesized via an unconventional route starting from 1-b -D-(ribofuranosyl)-2-nitroimidazole (AZR), with a change of configuration at the C-2-position to afford 1-b -D-(arabinofuranosyl)-2-nitroimidazole (b -AZA, 7). Nucleophilic iodination of the 5-Otoluenesulfonyl-2,3-di-O-acetyl precursor of b -AZA, 9, followed by deprotection, afforded 1 in satisfactory yield. b -IAZA (1) was also synthesized from 7 using molecular iodine and triphenylphosphine.