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 substi...

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Detalles Bibliográficos
Autores principales: Križková, Petra, Wieczorek, Anna, Hammerschmidt, Friedrich
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer Vienna 2016
Materias:
Original Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5225226/
https://www.ncbi.nlm.nih.gov/pubmed/28127094
http://dx.doi.org/10.1007/s00706-016-1874-8
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author Križková, Petra
Wieczorek, Anna
Hammerschmidt, Friedrich
author_facet Križková, Petra
Wieczorek, Anna
Hammerschmidt, Friedrich
author_sort Križková, Petra
collection PubMed
description 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: [Image: see text]
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spelling pubmed-52252262017-01-24 Efficient preparation of 2-nitroimidazole nucleosides as precursors for hypoxia PET tracers Križková, Petra Wieczorek, Anna Hammerschmidt, Friedrich Monatsh Chem Original Paper 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: [Image: see text] Springer Vienna 2016-12-07 2017 /pmc/articles/PMC5225226/ /pubmed/28127094 http://dx.doi.org/10.1007/s00706-016-1874-8 Text en © The Author(s) 2016 Open AccessThis article is distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made.
spellingShingle Original Paper
Križková, Petra
Wieczorek, Anna
Hammerschmidt, Friedrich
Efficient preparation of 2-nitroimidazole nucleosides as precursors for hypoxia PET tracers
title Efficient preparation of 2-nitroimidazole nucleosides as precursors for hypoxia PET tracers
title_full Efficient preparation of 2-nitroimidazole nucleosides as precursors for hypoxia PET tracers
title_fullStr Efficient preparation of 2-nitroimidazole nucleosides as precursors for hypoxia PET tracers
title_full_unstemmed Efficient preparation of 2-nitroimidazole nucleosides as precursors for hypoxia PET tracers
title_short Efficient preparation of 2-nitroimidazole nucleosides as precursors for hypoxia PET tracers
title_sort efficient preparation of 2-nitroimidazole nucleosides as precursors for hypoxia pet tracers
topic Original Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5225226/
https://www.ncbi.nlm.nih.gov/pubmed/28127094
http://dx.doi.org/10.1007/s00706-016-1874-8
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