2,6-Bis-arylmethyloxy-5-hydroxychromones with antiviral activity against both hepatitis C virus (HCV) and SARS-associated coronavirus (SCV).
Identifieur interne : 001543 ( PubMed/Checkpoint ); précédent : 001542; suivant : 0015442,6-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 ; Hye Ri Park ; Kyung Bo Kim ; Chaewoon Lee ; Suh Young Cho ; Jihoon Kang ; Hyunjun Yoon ; Dong-Eun Kim ; Hyunah Choo ; Yong-Joo Jeong ; Youhoon ChongSource :
- European journal of medicinal chemistry [ 1768-3254 ] ; 2011.
Descripteurs français
- KwdFr :
- 4H-1-Benzopyran-4-ones (), 4H-1-Benzopyran-4-ones (pharmacologie), 4H-1-Benzopyran-4-ones (synthèse chimique), 4H-1-Benzopyran-4-ones (toxicité), Antiviraux (), Antiviraux (pharmacologie), Antiviraux (synthèse chimique), Antiviraux (toxicité), Concentration inhibitrice 50, Hepacivirus (), Humains, Lignée cellulaire tumorale, Virus du SRAS ().
- MESH :
- pharmacologie : 4H-1-Benzopyran-4-ones, Antiviraux.
- synthèse chimique : 4H-1-Benzopyran-4-ones, Antiviraux.
- toxicité : 4H-1-Benzopyran-4-ones, Antiviraux.
- 4H-1-Benzopyran-4-ones, Antiviraux, Concentration inhibitrice 50, Hepacivirus, Humains, Lignée cellulaire tumorale, Virus du SRAS.
English descriptors
- KwdEn :
- Antiviral Agents (chemical synthesis), Antiviral Agents (chemistry), Antiviral Agents (pharmacology), Antiviral Agents (toxicity), Cell Line, Tumor, Chromones (chemical synthesis), Chromones (chemistry), Chromones (pharmacology), Chromones (toxicity), Hepacivirus (drug effects), Humans, Inhibitory Concentration 50, SARS Virus (drug effects).
- MESH :
- chemical , chemical synthesis : Antiviral Agents, Chromones.
- chemical , chemistry : Antiviral Agents, Chromones.
- chemical , pharmacology : Antiviral Agents, Chromones.
- chemical , toxicity : Antiviral Agents, Chromones.
- drug effects : Hepacivirus, SARS Virus.
- Cell Line, Tumor, Humans, Inhibitory Concentration 50.
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 (EC(50) = 4 μM) as well as SCV (IC(50) = 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.
DOI: 10.1016/j.ejmech.2011.09.005
PubMed: 21925774
Affiliations:
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first="Mi-Sun" last="Yu">Mi-Sun Yu</name></author><author><name sortKey="Park, Hye Ri" sort="Park, Hye Ri" uniqKey="Park H" first="Hye Ri" last="Park">Hye Ri Park</name></author><author><name sortKey="Kim, Kyung Bo" sort="Kim, Kyung Bo" uniqKey="Kim K" first="Kyung Bo" last="Kim">Kyung Bo Kim</name></author><author><name sortKey="Lee, Chaewoon" sort="Lee, Chaewoon" uniqKey="Lee C" first="Chaewoon" last="Lee">Chaewoon Lee</name></author><author><name sortKey="Cho, Suh Young" sort="Cho, Suh Young" uniqKey="Cho S" first="Suh Young" last="Cho">Suh Young Cho</name></author><author><name sortKey="Kang, Jihoon" sort="Kang, Jihoon" uniqKey="Kang J" first="Jihoon" last="Kang">Jihoon Kang</name></author><author><name sortKey="Yoon, Hyunjun" sort="Yoon, Hyunjun" uniqKey="Yoon H" first="Hyunjun" last="Yoon">Hyunjun Yoon</name></author><author><name sortKey="Kim, Dong Eun" sort="Kim, Dong Eun" uniqKey="Kim D" first="Dong-Eun" last="Kim">Dong-Eun Kim</name></author><author><name sortKey="Choo, 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wicri:stream="Checkpoint" wicri:step="PubMed">001543</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">2,6-Bis-arylmethyloxy-5-hydroxychromones with antiviral activity against both hepatitis C virus (HCV) and SARS-associated coronavirus (SCV).</title><author><name sortKey="Kim, Mi Kyoung" sort="Kim, Mi Kyoung" uniqKey="Kim M" first="Mi Kyoung" last="Kim">Mi Kyoung Kim</name><affiliation wicri:level="1"><nlm:affiliation>Department of Bioscience and Biotechnology, Bio/Molecular Informatics Center, Konkuk University, Hwayang-dong, Gwangjin-gu, Seoul 143-701, Republic of Korea.</nlm:affiliation><country xml:lang="fr">Corée du Sud</country><wicri:regionArea>Department of Bioscience and Biotechnology, Bio/Molecular Informatics Center, Konkuk University, Hwayang-dong, Gwangjin-gu, Seoul 143-701</wicri:regionArea><placeName><settlement type="city">Séoul</settlement><region type="capital">Région capitale de Séoul</region></placeName></affiliation></author><author><name sortKey="Yu, Mi Sun" sort="Yu, Mi Sun" uniqKey="Yu M" first="Mi-Sun" last="Yu">Mi-Sun Yu</name></author><author><name sortKey="Park, Hye Ri" sort="Park, Hye Ri" uniqKey="Park H" first="Hye Ri" last="Park">Hye Ri Park</name></author><author><name sortKey="Kim, Kyung Bo" sort="Kim, Kyung Bo" uniqKey="Kim K" first="Kyung Bo" last="Kim">Kyung Bo Kim</name></author><author><name sortKey="Lee, Chaewoon" sort="Lee, Chaewoon" uniqKey="Lee C" first="Chaewoon" last="Lee">Chaewoon Lee</name></author><author><name sortKey="Cho, Suh Young" sort="Cho, Suh Young" uniqKey="Cho S" first="Suh Young" last="Cho">Suh Young Cho</name></author><author><name sortKey="Kang, Jihoon" sort="Kang, Jihoon" uniqKey="Kang J" first="Jihoon" last="Kang">Jihoon Kang</name></author><author><name sortKey="Yoon, Hyunjun" sort="Yoon, Hyunjun" uniqKey="Yoon H" first="Hyunjun" last="Yoon">Hyunjun Yoon</name></author><author><name sortKey="Kim, Dong Eun" sort="Kim, Dong Eun" uniqKey="Kim D" first="Dong-Eun" last="Kim">Dong-Eun Kim</name></author><author><name sortKey="Choo, Hyunah" sort="Choo, Hyunah" uniqKey="Choo H" first="Hyunah" last="Choo">Hyunah Choo</name></author><author><name sortKey="Jeong, Yong Joo" sort="Jeong, Yong Joo" uniqKey="Jeong Y" first="Yong-Joo" last="Jeong">Yong-Joo Jeong</name></author><author><name sortKey="Chong, Youhoon" sort="Chong, Youhoon" uniqKey="Chong Y" first="Youhoon" last="Chong">Youhoon Chong</name></author></analytic><series><title level="j">European journal of medicinal chemistry</title><idno type="eISSN">1768-3254</idno><imprint><date when="2011" type="published">2011</date></imprint></series></biblStruct></sourceDesc></fileDesc><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>Antiviral Agents (toxicity)</term><term>Cell Line, Tumor</term><term>Chromones (chemical synthesis)</term><term>Chromones (chemistry)</term><term>Chromones (pharmacology)</term><term>Chromones (toxicity)</term><term>Hepacivirus (drug effects)</term><term>Humans</term><term>Inhibitory Concentration 50</term><term>SARS Virus (drug effects)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>4H-1-Benzopyran-4-ones ()</term><term>4H-1-Benzopyran-4-ones (pharmacologie)</term><term>4H-1-Benzopyran-4-ones (synthèse chimique)</term><term>4H-1-Benzopyran-4-ones (toxicité)</term><term>Antiviraux ()</term><term>Antiviraux (pharmacologie)</term><term>Antiviraux (synthèse chimique)</term><term>Antiviraux (toxicité)</term><term>Concentration inhibitrice 50</term><term>Hepacivirus ()</term><term>Humains</term><term>Lignée cellulaire tumorale</term><term>Virus du SRAS ()</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Antiviral Agents</term><term>Chromones</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Antiviral Agents</term><term>Chromones</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Antiviral Agents</term><term>Chromones</term></keywords><keywords scheme="MESH" type="chemical" qualifier="toxicity" xml:lang="en"><term>Antiviral Agents</term><term>Chromones</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Hepacivirus</term><term>SARS Virus</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>4H-1-Benzopyran-4-ones</term><term>Antiviraux</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>4H-1-Benzopyran-4-ones</term><term>Antiviraux</term></keywords><keywords scheme="MESH" qualifier="toxicité" xml:lang="fr"><term>4H-1-Benzopyran-4-ones</term><term>Antiviraux</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Cell Line, Tumor</term><term>Humans</term><term>Inhibitory Concentration 50</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>4H-1-Benzopyran-4-ones</term><term>Antiviraux</term><term>Concentration inhibitrice 50</term><term>Hepacivirus</term><term>Humains</term><term>Lignée cellulaire tumorale</term><term>Virus du SRAS</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 (EC(50) = 4 μM) as well as SCV (IC(50) = 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><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">21925774</PMID><DateCompleted><Year>2012</Year><Month>02</Month><Day>13</Day></DateCompleted><DateRevised><Year>2020</Year><Month>04</Month><Day>03</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1768-3254</ISSN><JournalIssue CitedMedium="Internet"><Volume>46</Volume><Issue>11</Issue><PubDate><Year>2011</Year><Month>Nov</Month></PubDate></JournalIssue><Title>European journal of medicinal chemistry</Title><ISOAbbreviation>Eur J Med Chem</ISOAbbreviation></Journal><ArticleTitle>2,6-Bis-arylmethyloxy-5-hydroxychromones with antiviral activity against both hepatitis C virus (HCV) and SARS-associated coronavirus (SCV).</ArticleTitle><Pagination><MedlinePgn>5698-704</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1016/j.ejmech.2011.09.005</ELocationID><Abstract><AbstractText>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 (EC(50) = 4 μM) as well as SCV (IC(50) = 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.</AbstractText><CopyrightInformation>Copyright © 2011 Elsevier Masson SAS. All rights reserved.</CopyrightInformation></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Kim</LastName><ForeName>Mi Kyoung</ForeName><Initials>MK</Initials><AffiliationInfo><Affiliation>Department of Bioscience and Biotechnology, Bio/Molecular Informatics Center, Konkuk University, Hwayang-dong, Gwangjin-gu, Seoul 143-701, Republic of Korea.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Yu</LastName><ForeName>Mi-Sun</ForeName><Initials>MS</Initials></Author><Author ValidYN="Y"><LastName>Park</LastName><ForeName>Hye Ri</ForeName><Initials>HR</Initials></Author><Author ValidYN="Y"><LastName>Kim</LastName><ForeName>Kyung Bo</ForeName><Initials>KB</Initials></Author><Author ValidYN="Y"><LastName>Lee</LastName><ForeName>Chaewoon</ForeName><Initials>C</Initials></Author><Author ValidYN="Y"><LastName>Cho</LastName><ForeName>Suh Young</ForeName><Initials>SY</Initials></Author><Author ValidYN="Y"><LastName>Kang</LastName><ForeName>Jihoon</ForeName><Initials>J</Initials></Author><Author ValidYN="Y"><LastName>Yoon</LastName><ForeName>Hyunjun</ForeName><Initials>H</Initials></Author><Author ValidYN="Y"><LastName>Kim</LastName><ForeName>Dong-Eun</ForeName><Initials>DE</Initials></Author><Author ValidYN="Y"><LastName>Choo</LastName><ForeName>Hyunah</ForeName><Initials>H</Initials></Author><Author ValidYN="Y"><LastName>Jeong</LastName><ForeName>Yong-Joo</ForeName><Initials>YJ</Initials></Author><Author ValidYN="Y"><LastName>Chong</LastName><ForeName>Youhoon</ForeName><Initials>Y</Initials></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2011</Year><Month>09</Month><Day>08</Day></ArticleDate></Article><MedlineJournalInfo><Country>France</Country><MedlineTA>Eur J Med Chem</MedlineTA><NlmUniqueID>0420510</NlmUniqueID><ISSNLinking>0223-5234</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000998">Antiviral Agents</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D002867">Chromones</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D000998" MajorTopicYN="N">Antiviral Agents</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="Y">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName><QualifierName UI="Q000633" MajorTopicYN="N">toxicity</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D045744" MajorTopicYN="N">Cell Line, Tumor</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D002867" MajorTopicYN="N">Chromones</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="Y">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName><QualifierName UI="Q000633" MajorTopicYN="N">toxicity</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D016174" MajorTopicYN="N">Hepacivirus</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="Y">drug effects</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D006801" MajorTopicYN="N">Humans</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D020128" MajorTopicYN="N">Inhibitory Concentration 50</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D045473" 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IdType="pii">S0223-5234(11)00644-1</ArticleId><ArticleId IdType="doi">10.1016/j.ejmech.2011.09.005</ArticleId><ArticleId IdType="pmc">PMC7115508</ArticleId></ArticleIdList><ReferenceList><Reference><Citation>Antiviral Res. 2002 Sep;55(3):397-412</Citation><ArticleIdList><ArticleId IdType="pubmed">12206878</ArticleId></ArticleIdList></Reference></ReferenceList><ReferenceList><Reference><Citation>Bioorg Med Chem. 2010 Nov 1;18(21):7331-7</Citation><ArticleIdList><ArticleId IdType="pubmed">20888241</ArticleId></ArticleIdList></Reference></ReferenceList><ReferenceList><Reference><Citation>Science. 2000 Jan 28;287(5453):646-50</Citation><ArticleIdList><ArticleId IdType="pubmed">10649997</ArticleId></ArticleIdList></Reference></ReferenceList><ReferenceList><Reference><Citation>Science. 1999 Jul 2;285(5424):110-3</Citation><ArticleIdList><ArticleId IdType="pubmed">10390360</ArticleId></ArticleIdList></Reference></ReferenceList><ReferenceList><Reference><Citation>Bioorg Med Chem Lett. 2004 Jun 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Young Cho</name><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="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="Kim, Kyung Bo" sort="Kim, Kyung Bo" uniqKey="Kim K" first="Kyung Bo" last="Kim">Kyung Bo Kim</name><name sortKey="Lee, Chaewoon" sort="Lee, Chaewoon" uniqKey="Lee C" first="Chaewoon" last="Lee">Chaewoon Lee</name><name sortKey="Park, Hye Ri" sort="Park, Hye Ri" uniqKey="Park H" first="Hye Ri" last="Park">Hye Ri Park</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></noCountry><country name="Corée du Sud"><region name="Région capitale de Séoul"><name sortKey="Kim, Mi Kyoung" sort="Kim, Mi Kyoung" uniqKey="Kim M" first="Mi Kyoung" last="Kim">Mi Kyoung Kim</name></region></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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