Synthesis of 1‐β‐D‐(5‐Deoxy‐5‐iodoarabinofuranosyl)‐2‐nitroimidazole (β‐IAZA): A Novel Marker of Tissue Hypoxia.

Abstract

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Recent Advances on Radionuclide Labeled Hypoxia-Imaging Agents

“…These results suggested that further investigation on nitrobenzoimidazole and nitrotriazole as tumor hypoxia markers was needed [40]. (11) and fell in the optimum range of an ideal hypoxic marker (0.01~0.1). In vivo distribution was performed in mammary tumor-bearing rats using a gamma camera and associated computer.…”

“…(4)). The -IAZA was synthesized via an unconventional route in satisfactory yield with a change of configuration at the C-2'-position, which may be used as a novel marker of tissue hypoxia [11]. Radioiodinated IAZA analogues are evaluated using microPET and animals.…”

A One-Pot Synthesis of 1-α- And 1-β-D-Arabinofuranosyl-2-Nitroimidazoles: Synthons to the Markers of Tumor Hypoxia

“…[3,7,12] b-AZA (5) was prepared via an unconventional route starting from 1-b-D-(ribofuranosyl)-2-nitroimidazole (AZR), with a change of configuration at the C-2'-position. [6] Trace amounts of b-AZA were reported as a sideproduct in the a-AZA synthesis from 1-a-bromo-2,3,5-tri-O-benzoylarabinofuranose, but no chemical characterization was provided. [12] In the present study, both a-AZA and b-AZA were obtained by reacting 2-nitroimidazole with a mixture of a-and b-1-O-acetyl-2,3,5-tri-O-benzoyl-D-arabinofuranose (2) in the presence of stannic chloride, followed by deprotection in the presence of ammonia/methanol (Scheme 1).…”

“…The melting points, 1 H and 13 C NMR spectra for 5 and 6 were identical to those reported previously. [6,7] ABBREVIATIONS AZA 1-D-arabinofuranosyl-2-nitroimidazole IAZA 1-D-(5-deoxy-5-iodoarabinofuranosyl)-2-nitroimidazole DDQ 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone AZR 1-b-D-(ribofuranosyl)-2-nitroimidazole Hg(CN) 2 mercuric cyanide…”

“…[9] An alternative approach to synthesize b-AZA via inversion of configuration at C-2' of the corresponding b-azomycin riboside has been reported. [6] To date there have been no reports of a one pot synthesis to provide useful yields of both a-and b-arabinofuranosyl azomycin nucleosides in reasonable yields. We now report a procedure where both a-and b-anomers are synthesized in good yield in a single reaction.…”