2,6-Bis-arylmethyloxy-5-hydroxychromones with antiviral activity against both hepatitis C virus (HCV) and SARS-associated coronavirus (SCV)
Identifieur interne : 002392 ( Main/Exploration ); précédent : 002391; suivant : 0023932,6-Bis-arylmethyloxy-5-hydroxychromones with antiviral activity against both hepatitis C virus (HCV) and SARS-associated coronavirus (SCV)
Auteurs : MI KYOUNG KIM [Corée du Sud] ; Mi-Sun Yu [Corée du Sud] ; HYE RI PARKA [Corée du Sud] ; KYUNG BO KIM [Corée du Sud] ; Chaewoon Lee [Corée du Sud] ; SUH YOUNG CHO [Corée du Sud] ; Jihoon Kang [Corée du Sud] ; Hyunjun Yoon [Corée du Sud] ; Dong-Eun Kim [Corée du Sud] ; Hyunah Choo [Corée du Sud] ; Yong-Joo Jeong [Corée du Sud] ; Youhoon Chong [Corée du Sud]Source :
- European journal of medicinal chemistry [ 0223-5234 ] ; 2011.
Descripteurs français
- Pascal (Inist)
- Dérivé de la chromone, Antiviral, Virus syndrome respiratoire aigu sévère, Virus hépatite C, Relation structure activité, Dérivé du benzène, Hétérocycle oxygène, Synthèse chimique, Composé bicyclique, Composé aromatique, Cétonephénols, Ether, In vitro, 1-Benzopyran-4-one(6-[3-chlorobenzyloxy]-5-hydroxy-2-[3-iodobenzyloxy]).
English descriptors
- KwdEn :
Abstract
In this study, as a bioisosteric alternative scaffold of the antiviral aryl diketoacids (ADKs), we used 5-hydroxychromone on which two arylmethyloxy substituents were installed. The 5-hydroxychromones (5b-5g) thus prepared showed anti-HCV activity and, depending on the aromatic substituents on the 2-arylmethyloxy moiety, some of the derivatives (5b-5f) were also active against SCV. In addition, unlike the ADKs which showed selective inhibition against the helicase activity of the SCV NTPase/helicase, the 5-hydroxychromones (5b-5f) were active against both NTPase and helicase activities of the target enzyme. Among those, 3-iodobenzyloxy-substituted derivative 5e showed the most potent activity against HCV (ECso = 4 μM) as well as SCV (IC50 = 4 μM for ATPase activity, 11 μM for helicase activity) and this might be used as a platform structure for future development of the multi-target or broad-spectrum antivirals.
Affiliations:
Links toward previous steps (curation, corpus...)
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Le document en format XML
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<author><name sortKey="Suh Young Cho" sort="Suh Young Cho" uniqKey="Suh Young Cho" last="Suh Young Cho">SUH YOUNG CHO</name>
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<author><name sortKey="Chong, Youhoon" sort="Chong, Youhoon" uniqKey="Chong Y" first="Youhoon" last="Chong">Youhoon Chong</name>
<affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Department of Bioscience and Biotechnology, Bio/Molecular Informatics Center, Konkuk University, Hwayang-dong</s1>
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<sourceDesc><biblStruct><analytic><title xml:lang="en" level="a">2,6-Bis-arylmethyloxy-5-hydroxychromones with antiviral activity against both hepatitis C virus (HCV) and SARS-associated coronavirus (SCV)</title>
<author><name sortKey="Mi Kyoung Kim" sort="Mi Kyoung Kim" uniqKey="Mi Kyoung Kim" last="Mi Kyoung Kim">MI KYOUNG KIM</name>
<affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Department of Bioscience and Biotechnology, Bio/Molecular Informatics Center, Konkuk University, Hwayang-dong</s1>
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<author><name sortKey="Yu, Mi Sun" sort="Yu, Mi Sun" uniqKey="Yu M" first="Mi-Sun" last="Yu">Mi-Sun Yu</name>
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<author><name sortKey="Hye Ri Parka" sort="Hye Ri Parka" uniqKey="Hye Ri Parka" last="Hye Ri Parka">HYE RI PARKA</name>
<affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Department of Bioscience and Biotechnology, Bio/Molecular Informatics Center, Konkuk University, Hwayang-dong</s1>
<s2>Gwangjin-gu, Seoul 143-701</s2>
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<region type="capital">Région capitale de Séoul</region>
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<author><name sortKey="Kyung Bo Kim" sort="Kyung Bo Kim" uniqKey="Kyung Bo Kim" last="Kyung Bo Kim">KYUNG BO KIM</name>
<affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Department of Bioscience and Biotechnology, Bio/Molecular Informatics Center, Konkuk University, Hwayang-dong</s1>
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<author><name sortKey="Lee, Chaewoon" sort="Lee, Chaewoon" uniqKey="Lee C" first="Chaewoon" last="Lee">Chaewoon Lee</name>
<affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Department of Bioscience and Biotechnology, Bio/Molecular Informatics Center, Konkuk University, Hwayang-dong</s1>
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<author><name sortKey="Suh Young Cho" sort="Suh Young Cho" uniqKey="Suh Young Cho" last="Suh Young Cho">SUH YOUNG CHO</name>
<affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Department of Bioscience and Biotechnology, Bio/Molecular Informatics Center, Konkuk University, Hwayang-dong</s1>
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<author><name sortKey="Kang, Jihoon" sort="Kang, Jihoon" uniqKey="Kang J" first="Jihoon" last="Kang">Jihoon Kang</name>
<affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Department of Bioscience and Biotechnology, Bio/Molecular Informatics Center, Konkuk University, Hwayang-dong</s1>
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<author><name sortKey="Yoon, Hyunjun" sort="Yoon, Hyunjun" uniqKey="Yoon H" first="Hyunjun" last="Yoon">Hyunjun Yoon</name>
<affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Department of Bioscience and Biotechnology, Bio/Molecular Informatics Center, Konkuk University, Hwayang-dong</s1>
<s2>Gwangjin-gu, Seoul 143-701</s2>
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<region type="capital">Région capitale de Séoul</region>
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<author><name sortKey="Kim, Dong Eun" sort="Kim, Dong Eun" uniqKey="Kim D" first="Dong-Eun" last="Kim">Dong-Eun Kim</name>
<affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Department of Bioscience and Biotechnology, Bio/Molecular Informatics Center, Konkuk University, Hwayang-dong</s1>
<s2>Gwangjin-gu, Seoul 143-701</s2>
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<author><name sortKey="Choo, Hyunah" sort="Choo, Hyunah" uniqKey="Choo H" first="Hyunah" last="Choo">Hyunah Choo</name>
<affiliation wicri:level="1"><inist:fA14 i1="03"><s1>Neuro-Medicine Center, Korea Institute of Science and Technology, 39-1 Hawolgok-dong</s1>
<s2>Seoungbuk-gu, Seoul 136-791</s2>
<s3>KOR</s3>
<sZ>10 aut.</sZ>
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<country>Corée du Sud</country>
<placeName><settlement type="city">Séoul</settlement>
<region type="capital">Région capitale de Séoul</region>
</placeName>
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</author>
<author><name sortKey="Jeong, Yong Joo" sort="Jeong, Yong Joo" uniqKey="Jeong Y" first="Yong-Joo" last="Jeong">Yong-Joo Jeong</name>
<affiliation wicri:level="1"><inist:fA14 i1="02"><s1>Department of Bio and Nanochemistry, Kookmin University</s1>
<s2>Seoul 136-702</s2>
<s3>KOR</s3>
<sZ>2 aut.</sZ>
<sZ>11 aut.</sZ>
</inist:fA14>
<country>Corée du Sud</country>
<placeName><settlement type="city">Séoul</settlement>
<region type="capital">Région capitale de Séoul</region>
</placeName>
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<author><name sortKey="Chong, Youhoon" sort="Chong, Youhoon" uniqKey="Chong Y" first="Youhoon" last="Chong">Youhoon Chong</name>
<affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Department of Bioscience and Biotechnology, Bio/Molecular Informatics Center, Konkuk University, Hwayang-dong</s1>
<s2>Gwangjin-gu, Seoul 143-701</s2>
<s3>KOR</s3>
<sZ>1 aut.</sZ>
<sZ>3 aut.</sZ>
<sZ>4 aut.</sZ>
<sZ>5 aut.</sZ>
<sZ>6 aut.</sZ>
<sZ>7 aut.</sZ>
<sZ>8 aut.</sZ>
<sZ>9 aut.</sZ>
<sZ>12 aut.</sZ>
</inist:fA14>
<country>Corée du Sud</country>
<placeName><settlement type="city">Séoul</settlement>
<region type="capital">Région capitale de Séoul</region>
</placeName>
</affiliation>
</author>
</analytic>
<series><title level="j" type="main">European journal of medicinal chemistry</title>
<title level="j" type="abbreviated">Eur. j. med. chem.</title>
<idno type="ISSN">0223-5234</idno>
<imprint><date when="2011">2011</date>
</imprint>
</series>
</biblStruct>
</sourceDesc>
<seriesStmt><title level="j" type="main">European journal of medicinal chemistry</title>
<title level="j" type="abbreviated">Eur. j. med. chem.</title>
<idno type="ISSN">0223-5234</idno>
</seriesStmt>
</fileDesc>
<profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Antiviral</term>
<term>Aromatic compound</term>
<term>Benzene derivatives</term>
<term>Bicyclic compound</term>
<term>Chemical synthesis</term>
<term>Chromone derivatives</term>
<term>Ether</term>
<term>Hepatitis C virus</term>
<term>In vitro</term>
<term>Ketophenols</term>
<term>Oxygen heterocycle</term>
<term>Severe acute respiratory syndrome virus</term>
<term>Structure activity relation</term>
</keywords>
<keywords scheme="Pascal" xml:lang="fr"><term>Dérivé de la chromone</term>
<term>Antiviral</term>
<term>Virus syndrome respiratoire aigu sévère</term>
<term>Virus hépatite C</term>
<term>Relation structure activité</term>
<term>Dérivé du benzène</term>
<term>Hétérocycle oxygène</term>
<term>Synthèse chimique</term>
<term>Composé bicyclique</term>
<term>Composé aromatique</term>
<term>Cétonephénols</term>
<term>Ether</term>
<term>In vitro</term>
<term>1-Benzopyran-4-one(6-[3-chlorobenzyloxy]-5-hydroxy-2-[3-iodobenzyloxy])</term>
</keywords>
</textClass>
</profileDesc>
</teiHeader>
<front><div type="abstract" xml:lang="en">In this study, as a bioisosteric alternative scaffold of the antiviral aryl diketoacids (ADKs), we used 5-hydroxychromone on which two arylmethyloxy substituents were installed. The 5-hydroxychromones (5b-5g) thus prepared showed anti-HCV activity and, depending on the aromatic substituents on the 2-arylmethyloxy moiety, some of the derivatives (5b-5f) were also active against SCV. In addition, unlike the ADKs which showed selective inhibition against the helicase activity of the SCV NTPase/helicase, the 5-hydroxychromones (5b-5f) were active against both NTPase and helicase activities of the target enzyme. Among those, 3-iodobenzyloxy-substituted derivative 5e showed the most potent activity against HCV (ECso = 4 μM) as well as SCV (IC50 = 4 μM for ATPase activity, 11 μM for helicase activity) and this might be used as a platform structure for future development of the multi-target or broad-spectrum antivirals.</div>
</front>
</TEI>
<affiliations><list><country><li>Corée du Sud</li>
</country>
<region><li>Région capitale de Séoul</li>
</region>
<settlement><li>Séoul</li>
</settlement>
</list>
<tree><country name="Corée du Sud"><region name="Région capitale de Séoul"><name sortKey="Mi Kyoung Kim" sort="Mi Kyoung Kim" uniqKey="Mi Kyoung Kim" last="Mi Kyoung Kim">MI KYOUNG KIM</name>
</region>
<name sortKey="Chong, Youhoon" sort="Chong, Youhoon" uniqKey="Chong Y" first="Youhoon" last="Chong">Youhoon Chong</name>
<name sortKey="Choo, Hyunah" sort="Choo, Hyunah" uniqKey="Choo H" first="Hyunah" last="Choo">Hyunah Choo</name>
<name sortKey="Hye Ri Parka" sort="Hye Ri Parka" uniqKey="Hye Ri Parka" last="Hye Ri Parka">HYE RI PARKA</name>
<name sortKey="Jeong, Yong Joo" sort="Jeong, Yong Joo" uniqKey="Jeong Y" first="Yong-Joo" last="Jeong">Yong-Joo Jeong</name>
<name sortKey="Kang, Jihoon" sort="Kang, Jihoon" uniqKey="Kang J" first="Jihoon" last="Kang">Jihoon Kang</name>
<name sortKey="Kim, Dong Eun" sort="Kim, Dong Eun" uniqKey="Kim D" first="Dong-Eun" last="Kim">Dong-Eun Kim</name>
<name sortKey="Kyung Bo Kim" sort="Kyung Bo Kim" uniqKey="Kyung Bo Kim" last="Kyung Bo Kim">KYUNG BO KIM</name>
<name sortKey="Lee, Chaewoon" sort="Lee, Chaewoon" uniqKey="Lee C" first="Chaewoon" last="Lee">Chaewoon Lee</name>
<name sortKey="Suh Young Cho" sort="Suh Young Cho" uniqKey="Suh Young Cho" last="Suh Young Cho">SUH YOUNG CHO</name>
<name sortKey="Yoon, Hyunjun" sort="Yoon, Hyunjun" uniqKey="Yoon H" first="Hyunjun" last="Yoon">Hyunjun Yoon</name>
<name sortKey="Yu, Mi Sun" sort="Yu, Mi Sun" uniqKey="Yu M" first="Mi-Sun" last="Yu">Mi-Sun Yu</name>
</country>
</tree>
</affiliations>
</record>
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