Synthesis of Iodoaminoimidazole Arabinoside (IAIA): A Potential Reductive Metabolite of the Spect Imaging Agent,Iodoazomycin Arabinoside (IAZA) |
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| Authors: | Herbert C. Lee Piyush Kumar Leonard I. Wiebe Robert McDonald John R. Mercer Kazue Ohkura |
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| Affiliation: | 1. Faculty of Pharmacy and Pharmaceutical Sciences;2. Department of Chemistry , University of Alberta , Edmonton, Alberta, Canada , T6G 2E1;3. Faculty of Pharmaceutical Sciences , Health Sciences University of Hokkaido , Ishikari-Tobetsu, Hokkaido, Japan , 061-0293 |
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| Abstract: | Abstract The stereospecific synthesis of 1-(5-deoxy-5-iodo-α-D-arabino-furanosyl)-2-aminoimidazole (iodoaminoimidazole arabinoside: IAIA, 2) is described. The reaction of the protected sugar bromide (8) and trifluoroacetamidoimidazole (10B) gave the coupled product (11B), which gave the free nucleoside (4) on deblocking. It was identical with AIA obtained by reduction of AZA (azomycin arabinoside), whose anomeric configuration was found to be a by the X-ray crystallography. |
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