Synthesis of 5-isoxazol-5-yl-2'-deoxyuridines exhibiting antiviral activity against HSV and several RNA viruses.
Identifieur interne : 000D40 ( PubMed/Corpus ); précédent : 000D39; suivant : 000D41Synthesis of 5-isoxazol-5-yl-2'-deoxyuridines exhibiting antiviral activity against HSV and several RNA viruses.
Auteurs : Yoon-Suk Lee ; Sun Min Park ; Byeang Hyean KimSource :
- Bioorganic & medicinal chemistry letters [ 1464-3405 ] ; 2009.
English descriptors
- KwdEn :
- Antiviral Agents (chemical synthesis), Antiviral Agents (chemistry), Antiviral Agents (pharmacology), Combinatorial Chemistry Techniques, Deoxyuridine (analogs & derivatives), Deoxyuridine (chemical synthesis), Deoxyuridine (chemistry), Deoxyuridine (pharmacology), Isoxazoles (chemical synthesis), Isoxazoles (chemistry), Isoxazoles (pharmacology), Microbial Sensitivity Tests, Molecular Structure, RNA Viruses (drug effects), Simplexvirus (drug effects).
- MESH :
- chemical , analogs & derivatives : Deoxyuridine.
- chemical , chemical synthesis : Antiviral Agents, Deoxyuridine, Isoxazoles.
- chemical , chemistry : Antiviral Agents, Deoxyuridine, Isoxazoles.
- chemical , pharmacology : Antiviral Agents, Deoxyuridine, Isoxazoles.
- drug effects : RNA Viruses, Simplexvirus.
- Combinatorial Chemistry Techniques, Microbial Sensitivity Tests, Molecular Structure.
Abstract
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.
DOI: 10.1016/j.bmcl.2008.12.103
PubMed: 19147352
Links to Exploration step
pubmed:19147352Le document en format XML
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<author><name sortKey="Lee, Yoon Suk" sort="Lee, Yoon Suk" uniqKey="Lee Y" first="Yoon-Suk" last="Lee">Yoon-Suk Lee</name>
<affiliation><nlm:affiliation>Department of Chemistry, BK School of Molecular Science, Pohang University of Science and Technology, Pohang 790-784, South Korea.</nlm:affiliation>
</affiliation>
</author>
<author><name sortKey="Park, Sun Min" sort="Park, Sun Min" uniqKey="Park S" first="Sun Min" last="Park">Sun Min Park</name>
</author>
<author><name sortKey="Kim, Byeang Hyean" sort="Kim, Byeang Hyean" uniqKey="Kim B" first="Byeang Hyean" last="Kim">Byeang Hyean Kim</name>
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<sourceDesc><biblStruct><analytic><title xml:lang="en">Synthesis of 5-isoxazol-5-yl-2'-deoxyuridines exhibiting antiviral activity against HSV and several RNA viruses.</title>
<author><name sortKey="Lee, Yoon Suk" sort="Lee, Yoon Suk" uniqKey="Lee Y" first="Yoon-Suk" last="Lee">Yoon-Suk Lee</name>
<affiliation><nlm:affiliation>Department of Chemistry, BK School of Molecular Science, Pohang University of Science and Technology, Pohang 790-784, South Korea.</nlm:affiliation>
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<author><name sortKey="Park, Sun Min" sort="Park, Sun Min" uniqKey="Park S" first="Sun Min" last="Park">Sun Min Park</name>
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<author><name sortKey="Kim, Byeang Hyean" sort="Kim, Byeang Hyean" uniqKey="Kim B" first="Byeang Hyean" last="Kim">Byeang Hyean Kim</name>
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<series><title level="j">Bioorganic & medicinal chemistry letters</title>
<idno type="eISSN">1464-3405</idno>
<imprint><date when="2009" type="published">2009</date>
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<profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Antiviral Agents (chemical synthesis)</term>
<term>Antiviral Agents (chemistry)</term>
<term>Antiviral Agents (pharmacology)</term>
<term>Combinatorial Chemistry Techniques</term>
<term>Deoxyuridine (analogs & derivatives)</term>
<term>Deoxyuridine (chemical synthesis)</term>
<term>Deoxyuridine (chemistry)</term>
<term>Deoxyuridine (pharmacology)</term>
<term>Isoxazoles (chemical synthesis)</term>
<term>Isoxazoles (chemistry)</term>
<term>Isoxazoles (pharmacology)</term>
<term>Microbial Sensitivity Tests</term>
<term>Molecular Structure</term>
<term>RNA Viruses (drug effects)</term>
<term>Simplexvirus (drug effects)</term>
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<keywords scheme="MESH" type="chemical" qualifier="analogs & derivatives" xml:lang="en"><term>Deoxyuridine</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Antiviral Agents</term>
<term>Deoxyuridine</term>
<term>Isoxazoles</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Antiviral Agents</term>
<term>Deoxyuridine</term>
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<term>Isoxazoles</term>
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<keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>RNA Viruses</term>
<term>Simplexvirus</term>
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<front><div type="abstract" xml:lang="en">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.</div>
</front>
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<DateRevised><Year>2013</Year>
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<Title>Bioorganic & medicinal chemistry letters</Title>
<ISOAbbreviation>Bioorg. Med. Chem. Lett.</ISOAbbreviation>
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<ArticleTitle>Synthesis of 5-isoxazol-5-yl-2'-deoxyuridines exhibiting antiviral activity against HSV and several RNA viruses.</ArticleTitle>
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<Abstract><AbstractText>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.</AbstractText>
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<AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Lee</LastName>
<ForeName>Yoon-Suk</ForeName>
<Initials>YS</Initials>
<AffiliationInfo><Affiliation>Department of Chemistry, BK School of Molecular Science, Pohang University of Science and Technology, Pohang 790-784, South Korea.</Affiliation>
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<Author ValidYN="Y"><LastName>Park</LastName>
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<Author ValidYN="Y"><LastName>Kim</LastName>
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<Language>eng</Language>
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