83416-39-1

Basic information

• Product Name: 1-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-2-nitroimidazole
• Synonyms: 1-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-2-nitroimidazole
• CAS NO: 83416-39-1
• Molecular Weight: 557.516
• Mol File: 83416-39-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-2-nitroimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-2-nitroimidazole(83416-39-1)
• EPA Substance Registry System: 1-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-2-nitroimidazole(83416-39-1)

Safety Data

• Hazardous Substances Data: 83416-39-1(Hazardous Substances Data)

Upstream product

• 56271-35-3 2,3,5-tri-O-benzoyl-α,β-D-arabinofuranosyl bromide 
• 83107-48-6 1-(trimethylsilyl)-2-nitroimidazole 
• 527-73-1 2-nitro-1H-imidazole 
• 57236-69-8 (3S,4R,5R)-2-acetoxy-5-((benzoyloxy)methyl)tetrahydrofuran-3,4-diyl dibenzoate 
• 98-88-4 benzoyl chloride 
• 83416-40-4 1-α-D-(arabinofuranosyl)-2-nitroimidazole 
• 56607-40-0 methyl D-arabinofuranoside 
• 7473-42-9 methyl tri-O-benzoyl-α-D-arabinofuranoside 
• 532-20-7 D-arabinofuranose 
• 4348-68-9 2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl bromide 
• 28697-53-2 D-arabinopyranose 

Downstream Products

• 911144-18-8 1-α-D-(3,5-di-O-benzoylarabinofuranosyl)-2-nitroimidazole 
• 1225013-24-0 1-α-D-(2,5-di-O-benzoylarabinofuranosyl)-2-nitroimidazole 
• 1225013-25-1 1-α-D-(3-O-benzoylarabinofuranosyl)-2-nitroimidazole 
• 1225013-26-2 1-α-D-(5-O-benzoylarabinofuranosyl)-2-nitroimidazole 
• 193150-92-4 1-(5-deoxy-5-iodo-α-D-arabinofuranosyl)-2-nitroimidazole 
• 250693-28-8 1-(α-D-arabinofuranosyl)-2-aminoimidazole 
• 193150-87-7 1-(2-benzoyl-α-D-arabinofuranosyl)-2-nitroimidazole 
• 83416-40-4 1-α-D-(arabinofuranosyl)-2-nitroimidazole 

Relevant articles and documents

Synthesis, radiofluorination, and hypoxia-selective studies of FRAZ: A configurational and positional analogue of the clinical hypoxia marker, [18F]-FAZA

The current work evaluates 1-α-d-(2-deoxy-2-fluororibofuranosyl)-2-nitroimidazole (FRAZ), a novel azomycin nucleoside that is a potential radiosensitizer of tumor hypoxia. FRAZ is a ribose analogue of 1-α-d-(2-deoxy-2-fluoroarabinofuranosyl)-2-nitroimidazole ([18F]-FAZA), a clinically used hypoxia marker. Preliminary assessment of the cytotoxicity and hypoxia-specific in vitro binding in HCT-110 colorectal cancer cells indicate that the radiosensitization properties of FRAZ are similar to that of FAZA, with a sensitizer enhancement ratio (SER) of ～1.8. An automated radiosynthesis of [18F]-FRAZ using a commercial automated synthesis unit (ASU) was established (synthesis time ～32 min; radiochemical yield (decay uncorrecetd) ～22%) to facilitate its application in PET-based diagnosis of hypoxic tumors.

An improved synthesis of α-AZA, α-AZP and α-AZG, the precursors to clinical markers of tissue hypoxia

α-[123I]-IAZA and α-[123I]-IAZP are experimental diagnostic radiopharmaceuticals which have been used clinically to diagnose hypoxia in a number of pathologies, including cancer, peripheral vascular disease, rheumatoid arthritis and brain trauma. These nitroimidazole nucleosides are synthesized from the non-iodinated nucleosides AZA, AZP and AZG, respectively. Earlier methods report low chemical yields for the synthesis of these precursors. The modified procedures now reported provide nearly quantitative yields of these compounds, thereby substantially reducing the cost and effort of synthesis.

Potential Radiosensitizing Agents. 6. 2-Nitroimidazole Nucleosides: Arabinofuranosyl and Hexopyranosyl Analogues

New 2-nitroimidazole nucleosides have been synthesized as radiosensitizers of hypoxic mammalian cells in an attempt to reduce the neurotoxicity and to increase the therapeutic efficacy of this class of agents.The trimethylsilyl derivative of 2-nitroimidaz