Synthesis of 5-isoxazol-5-yl-2′-deoxyuridines exhibiting antiviral activity against HSV and several RNA viruses

This paper describes a simple method for synthesizing a small library of 5-isoxazol-5-yl-2′-deoxyuridines from 5-iodo-2′-deoxyuridine. Nitrile oxides were generated in situ from oximes using a commercial bleaching agent; their cycloaddition with 5-ethynyl-2′-deoxyuridine yielded isoxazoles possessin...

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Autores principales: Lee, Yoon-Suk, Park, Sun Min, Kim, Byeang Hyean
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Published by Elsevier Ltd. 2009
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7126966/
https://www.ncbi.nlm.nih.gov/pubmed/19147352
http://dx.doi.org/10.1016/j.bmcl.2008.12.103
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author Lee, Yoon-Suk
Park, Sun Min
Kim, Byeang Hyean
author_facet Lee, Yoon-Suk
Park, Sun Min
Kim, Byeang Hyean
author_sort Lee, Yoon-Suk
collection PubMed
description This paper describes a simple method for synthesizing a small library of 5-isoxazol-5-yl-2′-deoxyuridines from 5-iodo-2′-deoxyuridine. Nitrile oxides were generated in situ from oximes using a commercial bleaching agent; their cycloaddition with 5-ethynyl-2′-deoxyuridine yielded isoxazoles possessing activity against herpes simplex viruses 1 and 2, Encephalomyocarditis virus, Coxsackie B3, and vesicular stomatitis virus; these isoxazoles were, however, inactive against corona virus, influenza virus, and HIV.
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spelling pubmed-71269662020-04-08 Synthesis of 5-isoxazol-5-yl-2′-deoxyuridines exhibiting antiviral activity against HSV and several RNA viruses Lee, Yoon-Suk Park, Sun Min Kim, Byeang Hyean Bioorg Med Chem Lett Article This paper describes a simple method for synthesizing a small library of 5-isoxazol-5-yl-2′-deoxyuridines from 5-iodo-2′-deoxyuridine. Nitrile oxides were generated in situ from oximes using a commercial bleaching agent; their cycloaddition with 5-ethynyl-2′-deoxyuridine yielded isoxazoles possessing activity against herpes simplex viruses 1 and 2, Encephalomyocarditis virus, Coxsackie B3, and vesicular stomatitis virus; these isoxazoles were, however, inactive against corona virus, influenza virus, and HIV. Published by Elsevier Ltd. 2009-02-15 2008-12-31 /pmc/articles/PMC7126966/ /pubmed/19147352 http://dx.doi.org/10.1016/j.bmcl.2008.12.103 Text en Copyright © 2009 Published by Elsevier Ltd. Since January 2020 Elsevier has created a COVID-19 resource centre with free information in English and Mandarin on the novel coronavirus COVID-19. The COVID-19 resource centre is hosted on Elsevier Connect, the company's public news and information website. Elsevier hereby grants permission to make all its COVID-19-related research that is available on the COVID-19 resource centre - including this research content - immediately available in PubMed Central and other publicly funded repositories, such as the WHO COVID database with rights for unrestricted research re-use and analyses in any form or by any means with acknowledgement of the original source. These permissions are granted for free by Elsevier for as long as the COVID-19 resource centre remains active.
spellingShingle Article
Lee, Yoon-Suk
Park, Sun Min
Kim, Byeang Hyean
Synthesis of 5-isoxazol-5-yl-2′-deoxyuridines exhibiting antiviral activity against HSV and several RNA viruses
title Synthesis of 5-isoxazol-5-yl-2′-deoxyuridines exhibiting antiviral activity against HSV and several RNA viruses
title_full Synthesis of 5-isoxazol-5-yl-2′-deoxyuridines exhibiting antiviral activity against HSV and several RNA viruses
title_fullStr Synthesis of 5-isoxazol-5-yl-2′-deoxyuridines exhibiting antiviral activity against HSV and several RNA viruses
title_full_unstemmed Synthesis of 5-isoxazol-5-yl-2′-deoxyuridines exhibiting antiviral activity against HSV and several RNA viruses
title_short Synthesis of 5-isoxazol-5-yl-2′-deoxyuridines exhibiting antiviral activity against HSV and several RNA viruses
title_sort synthesis of 5-isoxazol-5-yl-2′-deoxyuridines exhibiting antiviral activity against hsv and several rna viruses
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7126966/
https://www.ncbi.nlm.nih.gov/pubmed/19147352
http://dx.doi.org/10.1016/j.bmcl.2008.12.103
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