Efficient preparation of 2-nitroimidazole nucleosides as precursors for hypoxia PET tracers

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Efficient preparation of 2-nitroimidazole nucleosides as precursors for hypoxia PET tracers

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 influe...

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Preparation of Nucleosides Derived from 2-Nitroimidazole and d-Arabinose, d-Ribose, and d-Galactose by the Vorbrüggen Method and Their Conversion to Potential Precursors for Tracers To Image Hypoxia

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 (Vorbrüggen conditions). The α-anomer was formed in the former case and the β-anomers in the latter two cases (highly) selectively. When D-arabinose and D-ribose we...

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2-Nitroimidazole as Potential Nanoprobe in Hypoxia Imaging by MRI/PET

2-Nitroimidazole is radiosensitizer and serves as imaging contrast agent by 19Fand 31P MR methods. Despite the success of mesonidazole and SR-4554 compounds, very little is known of its hepato-cytotoxicity if it can be potential hypoxia imaging marker and non-toxic drug. Authors established the low oxygen, low energy metabolic ratio and gluconeogenesis in nitroimidazole induced hepatocytes and ...

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Preparation and Evaluation of Lu Labeled Nitroimidazole Derivative for Targeting Tumor Hypoxia

Hypoxia has been known be an important physiological parameter for tumor growth and has been reported to be the cause for poor response to chemotherapy. Mechanistically, tumor hypoxia results from an imbalance between oxygen delivery and oxygen consumption. The identification and quantification of tumor hypoxia may predict the out come and may identify patients who might benefit from concomitan...

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ژورنال

عنوان ژورنال: Monatshefte für Chemie - Chemical Monthly

سال: 2016

ISSN: 0026-9247,1434-4475

DOI: 10.1007/s00706-016-1874-8