220792-97-2Relevant academic research and scientific papers
Preparation of nucleosides derived from 2-nitroimidazole and d -arabinose, d -ribose, and d -Galactose by the Vorbrueggen method and their conversion to potential precursors for tracers to image hypoxia
Schweifer, Anna,Hammerschmidt, Friedrich
experimental part, p. 8159 - 8167 (2012/01/03)
2-Nitroimidazole was silylated using hexaethyldisilazane and then reacted with 1-O-acetyl derivatives of d-arabinose, d-ribose, and d-galactose in acetonitrile at mild temperatures (-20 °C to rt), catalyzed by triethylsilyl triflate (Vorbrueggen condition
Fluoroazomycin arabinoside (FAZA): Synthesis, 2H and 3H-labelling and preliminary biological evaluation of a novel 2-nitroimidazole marker of tissue hypoxia
Kumar,Stypinski,Xia,McEwan,Machulla,Wiebe
, p. 3 - 16 (2007/10/03)
1-α-D-(5-Fluoro-5-deoxyarabinofuranosyl)-2-nitroimidazole (fluoroazomycin alabinoside; FAZA) 6, a putative PET imaging agent when labelled with 18F, was synthesized by fluorination of 1-α-D-(2,3-di-O-acetylarabinofuranosyl)-2-nitroimidazole with DAST followed by deprotection. The C-5'-deuterated and tritiated analogues were prepared by NaCNBD3 or NaCNBT3 reduction of the protected C-5'-carbonyl intermediate 5, followed by C-5' fluorination and deprotection, to afford C-5' deuterated and C-5' tritiated FAZA, respectively. Preliminary in vivo biodistribution studies in a murine tumour model, and pharmacokinetic studies in rats indicated that 3H-FAZA has biodistribution, tumour uptake and pharmacokinetic properties similar to those of 123I-IAZA, a clinically-proven radiopharmaceutical for SPECT-imaging of hypoxic tissues.
