Abstract
2-Deoxy-D-ribose was converted to α/β-mixtures of methyl 3-O-acetyl- and methyl 3-O-benzoyl-2-deoxy-5-(p-toluenesulfonyl)-D-ribofuranosides. These were reacted with boron trichloride to generate ribofuranosyl chlorides, which afforded precursors for tracers to image tumor hypoxia on substitution with salts of 2-nitroimidazole. The anomeric ratio of the nucleosides was delicately influenced by the reaction conditions.Graphical abstract
Highlights
Tumor hypoxia has a negative prognosis predictive value for solid tumors, because it is associated with tumor aggressiveness, metastasis, and aberrant angiogenesis [1,2,3]
The synthesis of known 2-nitroimidazole nucleosides derived from 2-deoxy-D-ribose used as precursors for tracers was shortened if tosylation is performed at the beginning instead of at the end of the reaction sequence
1H, 13C (J-modulated; not J-modulated spectra were recorded of 2-nitroimidazole derivatives) NMR spectra were recorded in CDCl3 on a Bruker AV III 400 (1H: 400.27 MHz, 13C: 100.65 MHz), AV 400 (1H: 400.13 MHz, 13C: 100.61 MHz), and AV III 600 (1H: 600.13 MHz, 13C: 150.90 MHz) spectrometer at 25 °C, respectively
Summary
Tumor hypoxia has a negative prognosis predictive value for solid tumors, because it is associated with tumor aggressiveness, metastasis, and aberrant angiogenesis [1,2,3]. It reflects increased resistance to anticancer treatment by radio- and chemotherapy. It is in the interest of cancer patients to identify and target hypoxic areas in solid tumors [4, 5].
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