Synthesis and antiviral evaluation of 7-O-arylmethylquercetin derivatives against SARS-associated coronavirus (SCV) and hepatitis C virus (HCV).
Identifieur interne : 002445 ( Ncbi/Merge ); précédent : 002444; suivant : 002446Synthesis and antiviral evaluation of 7-O-arylmethylquercetin derivatives against SARS-associated coronavirus (SCV) and hepatitis C virus (HCV).
Auteurs : Hye Ri Park [Corée du Sud] ; Hyunjun Yoon ; Mi Kyoung Kim ; Sung Dae Lee ; Youhoon ChongSource :
- Archives of pharmacal research [ 0253-6269 ] ; 2012.
Descripteurs français
- KwdFr :
- MESH :
- pharmacologie : Antiviraux, Quercétine.
- physiologie : Hepacivirus, Virus du SRAS.
- synthèse chimique : Antiviraux, Quercétine.
- Hepacivirus, Humains, Lignée cellulaire tumorale, Réplication virale, Virus du SRAS.
English descriptors
- KwdEn :
- MESH :
- chemical , chemical synthesis : Antiviral Agents, Quercetin.
- chemical , pharmacology : Antiviral Agents, Quercetin.
- drug effects : Hepacivirus, SARS Virus, Virus Replication.
- physiology : Hepacivirus, SARS Virus.
- Cell Line, Tumor, Humans.
Abstract
Aryl diketoacid (ADK) is well known for antiviral activity which can be enhanced by introduction of an aromatic arylmethyl substituent. A natural flavonoid quercetin has a 3,5-dihydroxychromone pharmacophore which is in bioisosteric relationship with the 1,3-diketoacid moiety of the ADK. Thus, it was of our interest to test the antiviral activity of the quercetin derivatives with an arylmethyl group attached. In this study, we prepared a series of the 7-O-arylmethylquercetin derivatives with various aromatic substituents and evaluated their antiviral activity against the SARS-associated coronavirus (SARS-CoV, SCV) as well as hepatitis C virus (HCV). Single difference in the aromatic substituent fine-tuned the biological activity of the 7-O-arylmethylquercetin derivatives to result in two different classes of derivatives selectively active against SCV and HCV.
DOI: 10.1007/s12272-012-0108-9
PubMed: 22297745
Links toward previous steps (curation, corpus...)
- to stream PubMed, to step Corpus: 001412
- to stream PubMed, to step Curation: 001412
- to stream PubMed, to step Checkpoint: 001272
Links to Exploration step
pubmed:22297745Le document en format XML
<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Synthesis and antiviral evaluation of 7-O-arylmethylquercetin derivatives against SARS-associated coronavirus (SCV) and hepatitis C virus (HCV).</title><author><name sortKey="Park, Hye Ri" sort="Park, Hye Ri" uniqKey="Park H" first="Hye Ri" last="Park">Hye Ri Park</name><affiliation wicri:level="1"><nlm:affiliation>Department of Bioscience and Biotechnology, Bio/Molecular Informatics Center, Konkuk University, Seoul 143-701, Korea.</nlm:affiliation><country xml:lang="fr">Corée du Sud</country><wicri:regionArea>Department of Bioscience and Biotechnology, Bio/Molecular Informatics Center, Konkuk University, 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="Yoon, Hyunjun" sort="Yoon, Hyunjun" uniqKey="Yoon H" first="Hyunjun" last="Yoon">Hyunjun Yoon</name></author><author><name sortKey="Kim, Mi Kyoung" sort="Kim, Mi Kyoung" uniqKey="Kim M" first="Mi Kyoung" last="Kim">Mi Kyoung Kim</name></author><author><name sortKey="Lee, Sung Dae" sort="Lee, Sung Dae" uniqKey="Lee S" first="Sung Dae" last="Lee">Sung Dae Lee</name></author><author><name sortKey="Chong, Youhoon" sort="Chong, Youhoon" uniqKey="Chong Y" first="Youhoon" last="Chong">Youhoon Chong</name></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2012">2012</date><idno type="RBID">pubmed:22297745</idno><idno type="pmid">22297745</idno><idno type="doi">10.1007/s12272-012-0108-9</idno><idno type="wicri:Area/PubMed/Corpus">001412</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">001412</idno><idno type="wicri:Area/PubMed/Curation">001412</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Curation">001412</idno><idno type="wicri:Area/PubMed/Checkpoint">001272</idno><idno type="wicri:explorRef" wicri:stream="Checkpoint" wicri:step="PubMed">001272</idno><idno type="wicri:Area/Ncbi/Merge">002445</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Synthesis and antiviral evaluation of 7-O-arylmethylquercetin derivatives against SARS-associated coronavirus (SCV) and hepatitis C virus (HCV).</title><author><name sortKey="Park, Hye Ri" sort="Park, Hye Ri" uniqKey="Park H" first="Hye Ri" last="Park">Hye Ri Park</name><affiliation wicri:level="1"><nlm:affiliation>Department of Bioscience and Biotechnology, Bio/Molecular Informatics Center, Konkuk University, Seoul 143-701, Korea.</nlm:affiliation><country xml:lang="fr">Corée du Sud</country><wicri:regionArea>Department of Bioscience and Biotechnology, Bio/Molecular Informatics Center, Konkuk University, 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="Yoon, Hyunjun" sort="Yoon, Hyunjun" uniqKey="Yoon H" first="Hyunjun" last="Yoon">Hyunjun Yoon</name></author><author><name sortKey="Kim, Mi Kyoung" sort="Kim, Mi Kyoung" uniqKey="Kim M" first="Mi Kyoung" last="Kim">Mi Kyoung Kim</name></author><author><name sortKey="Lee, Sung Dae" sort="Lee, Sung Dae" uniqKey="Lee S" first="Sung Dae" last="Lee">Sung Dae Lee</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">Archives of pharmacal research</title><idno type="ISSN">0253-6269</idno><imprint><date when="2012" type="published">2012</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Antiviral Agents (chemical synthesis)</term><term>Antiviral Agents (pharmacology)</term><term>Cell Line, Tumor</term><term>Hepacivirus (drug effects)</term><term>Hepacivirus (physiology)</term><term>Humans</term><term>Quercetin (chemical synthesis)</term><term>Quercetin (pharmacology)</term><term>SARS Virus (drug effects)</term><term>SARS Virus (physiology)</term><term>Virus Replication (drug effects)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Antiviraux (pharmacologie)</term><term>Antiviraux (synthèse chimique)</term><term>Hepacivirus ()</term><term>Hepacivirus (physiologie)</term><term>Humains</term><term>Lignée cellulaire tumorale</term><term>Quercétine (pharmacologie)</term><term>Quercétine (synthèse chimique)</term><term>Réplication virale ()</term><term>Virus du SRAS ()</term><term>Virus du SRAS (physiologie)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Antiviral Agents</term><term>Quercetin</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Antiviral Agents</term><term>Quercetin</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Hepacivirus</term><term>SARS Virus</term><term>Virus Replication</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Antiviraux</term><term>Quercétine</term></keywords><keywords scheme="MESH" qualifier="physiologie" xml:lang="fr"><term>Hepacivirus</term><term>Virus du SRAS</term></keywords><keywords scheme="MESH" qualifier="physiology" xml:lang="en"><term>Hepacivirus</term><term>SARS Virus</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Antiviraux</term><term>Quercétine</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Cell Line, Tumor</term><term>Humans</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Hepacivirus</term><term>Humains</term><term>Lignée cellulaire tumorale</term><term>Réplication virale</term><term>Virus du SRAS</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Aryl diketoacid (ADK) is well known for antiviral activity which can be enhanced by introduction of an aromatic arylmethyl substituent. A natural flavonoid quercetin has a 3,5-dihydroxychromone pharmacophore which is in bioisosteric relationship with the 1,3-diketoacid moiety of the ADK. Thus, it was of our interest to test the antiviral activity of the quercetin derivatives with an arylmethyl group attached. In this study, we prepared a series of the 7-O-arylmethylquercetin derivatives with various aromatic substituents and evaluated their antiviral activity against the SARS-associated coronavirus (SARS-CoV, SCV) as well as hepatitis C virus (HCV). Single difference in the aromatic substituent fine-tuned the biological activity of the 7-O-arylmethylquercetin derivatives to result in two different classes of derivatives selectively active against SCV and HCV.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">22297745</PMID><DateCompleted><Year>2012</Year><Month>09</Month><Day>28</Day></DateCompleted><DateRevised><Year>2020</Year><Month>03</Month><Day>25</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Print">0253-6269</ISSN><JournalIssue CitedMedium="Internet"><Volume>35</Volume><Issue>1</Issue><PubDate><Year>2012</Year><Month>Jan</Month></PubDate></JournalIssue><Title>Archives of pharmacal research</Title><ISOAbbreviation>Arch. Pharm. Res.</ISOAbbreviation></Journal><ArticleTitle>Synthesis and antiviral evaluation of 7-O-arylmethylquercetin derivatives against SARS-associated coronavirus (SCV) and hepatitis C virus (HCV).</ArticleTitle><Pagination><MedlinePgn>77-85</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1007/s12272-012-0108-9</ELocationID><Abstract><AbstractText>Aryl diketoacid (ADK) is well known for antiviral activity which can be enhanced by introduction of an aromatic arylmethyl substituent. A natural flavonoid quercetin has a 3,5-dihydroxychromone pharmacophore which is in bioisosteric relationship with the 1,3-diketoacid moiety of the ADK. Thus, it was of our interest to test the antiviral activity of the quercetin derivatives with an arylmethyl group attached. In this study, we prepared a series of the 7-O-arylmethylquercetin derivatives with various aromatic substituents and evaluated their antiviral activity against the SARS-associated coronavirus (SARS-CoV, SCV) as well as hepatitis C virus (HCV). Single difference in the aromatic substituent fine-tuned the biological activity of the 7-O-arylmethylquercetin derivatives to result in two different classes of derivatives selectively active against SCV and HCV.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Park</LastName><ForeName>Hye Ri</ForeName><Initials>HR</Initials><AffiliationInfo><Affiliation>Department of Bioscience and Biotechnology, Bio/Molecular Informatics Center, Konkuk University, Seoul 143-701, Korea.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Yoon</LastName><ForeName>Hyunjun</ForeName><Initials>H</Initials></Author><Author ValidYN="Y"><LastName>Kim</LastName><ForeName>Mi Kyoung</ForeName><Initials>MK</Initials></Author><Author ValidYN="Y"><LastName>Lee</LastName><ForeName>Sung Dae</ForeName><Initials>SD</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>2012</Year><Month>02</Month><Day>02</Day></ArticleDate></Article><MedlineJournalInfo><Country>Korea (South)</Country><MedlineTA>Arch Pharm Res</MedlineTA><NlmUniqueID>8000036</NlmUniqueID><ISSNLinking>0253-6269</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000998">Antiviral Agents</NameOfSubstance></Chemical><Chemical><RegistryNumber>9IKM0I5T1E</RegistryNumber><NameOfSubstance UI="D011794">Quercetin</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="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D045744" MajorTopicYN="N">Cell Line, Tumor</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D016174" MajorTopicYN="N">Hepacivirus</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="Y">drug effects</QualifierName><QualifierName UI="Q000502" MajorTopicYN="N">physiology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D006801" MajorTopicYN="N">Humans</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D011794" MajorTopicYN="N">Quercetin</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="Y">chemical synthesis</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D045473" MajorTopicYN="N">SARS Virus</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="Y">drug effects</QualifierName><QualifierName UI="Q000502" MajorTopicYN="N">physiology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D014779" MajorTopicYN="N">Virus Replication</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2011</Year><Month>06</Month><Day>18</Day></PubMedPubDate><PubMedPubDate PubStatus="accepted"><Year>2011</Year><Month>08</Month><Day>09</Day></PubMedPubDate><PubMedPubDate PubStatus="revised"><Year>2011</Year><Month>07</Month><Day>29</Day></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2012</Year><Month>2</Month><Day>3</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2012</Year><Month>2</Month><Day>3</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2012</Year><Month>9</Month><Day>29</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">22297745</ArticleId><ArticleId IdType="doi">10.1007/s12272-012-0108-9</ArticleId><ArticleId IdType="pmc">PMC7090976</ArticleId></ArticleIdList><ReferenceList><Reference><Citation>Clin Cancer Res. 1996 Apr;2(4):659-68</Citation><ArticleIdList><ArticleId IdType="pubmed">9816216</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>Antimicrob Agents Chemother. 2008 Feb;52(2):393-401</Citation><ArticleIdList><ArticleId IdType="pubmed">18039921</ArticleId></ArticleIdList></Reference></ReferenceList><ReferenceList><Reference><Citation>J Gen Virol. 1988 Jul;69 ( Pt 7):1749-51</Citation><ArticleIdList><ArticleId IdType="pubmed">2839607</ArticleId></ArticleIdList></Reference></ReferenceList><ReferenceList><Reference><Citation>J Nat Prod. 1992 Dec;55(12):1732-40</Citation><ArticleIdList><ArticleId IdType="pubmed">1338212</ArticleId></ArticleIdList></Reference></ReferenceList><ReferenceList><Reference><Citation>Bioorg Med Chem Lett. 2010 Oct 1;20(19):5709-12</Citation><ArticleIdList><ArticleId IdType="pubmed">20797857</ArticleId></ArticleIdList></Reference></ReferenceList><ReferenceList><Reference><Citation>J Virol Methods. 2003 Jun 30;110(2):201-9</Citation><ArticleIdList><ArticleId IdType="pubmed">12798249</ArticleId></ArticleIdList></Reference></ReferenceList><ReferenceList><Reference><Citation>Biol Pharm Bull. 1999 Oct;22(10):1122-6</Citation><ArticleIdList><ArticleId IdType="pubmed">10549869</ArticleId></ArticleIdList></Reference></ReferenceList><ReferenceList><Reference><Citation>Bioorg Med Chem Lett. 2009 Mar 15;19(6):1636-8</Citation><ArticleIdList><ArticleId IdType="pubmed">19233643</ArticleId></ArticleIdList></Reference></ReferenceList><ReferenceList><Reference><Citation>J Med Virol. 1985 Jan;15(1):71-9</Citation><ArticleIdList><ArticleId IdType="pubmed">2981979</ArticleId></ArticleIdList></Reference></ReferenceList><ReferenceList><Reference><Citation>Bioorg Med Chem Lett. 2009 Aug 15;19(16):4538-41</Citation><ArticleIdList><ArticleId IdType="pubmed">19625187</ArticleId></ArticleIdList></Reference></ReferenceList><ReferenceList><Reference><Citation>J Org Chem. 2003 Aug 22;68(17):6842-5</Citation><ArticleIdList><ArticleId IdType="pubmed">12919064</ArticleId></ArticleIdList></Reference></ReferenceList><ReferenceList><Reference><Citation>Bioorg Med Chem Lett. 2008 Aug 15;18(16):4661-5</Citation><ArticleIdList><ArticleId IdType="pubmed">18644717</ArticleId></ArticleIdList></Reference></ReferenceList><ReferenceList><Reference><Citation>Altern Med Rev. 2000 Jun;5(3):196-208</Citation><ArticleIdList><ArticleId IdType="pubmed">10869101</ArticleId></ArticleIdList></Reference></ReferenceList></PubmedData></pubmed><affiliations><list><country><li>Corée du Sud</li></country><region><li>Région capitale de Séoul</li></region><settlement><li>Séoul</li></settlement></list><tree><noCountry><name sortKey="Chong, Youhoon" sort="Chong, Youhoon" uniqKey="Chong Y" first="Youhoon" last="Chong">Youhoon Chong</name><name sortKey="Kim, Mi Kyoung" sort="Kim, Mi Kyoung" uniqKey="Kim M" first="Mi Kyoung" last="Kim">Mi Kyoung Kim</name><name sortKey="Lee, Sung Dae" sort="Lee, Sung Dae" uniqKey="Lee S" first="Sung Dae" last="Lee">Sung Dae Lee</name><name sortKey="Yoon, Hyunjun" sort="Yoon, Hyunjun" uniqKey="Yoon H" first="Hyunjun" last="Yoon">Hyunjun Yoon</name></noCountry><country name="Corée du Sud"><region name="Région capitale de Séoul"><name sortKey="Park, Hye Ri" sort="Park, Hye Ri" uniqKey="Park H" first="Hye Ri" last="Park">Hye Ri Park</name></region></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
EXPLOR_STEP=$WICRI_ROOT/Sante/explor/SrasV1/Data/Ncbi/Merge
HfdSelect -h $EXPLOR_STEP/biblio.hfd -nk 002445 | SxmlIndent | more
Ou
HfdSelect -h $EXPLOR_AREA/Data/Ncbi/Merge/biblio.hfd -nk 002445 | SxmlIndent | more
Pour mettre un lien sur cette page dans le réseau Wicri
{{Explor lien
|wiki= Sante
|area= SrasV1
|flux= Ncbi
|étape= Merge
|type= RBID
|clé= pubmed:22297745
|texte= Synthesis and antiviral evaluation of 7-O-arylmethylquercetin derivatives against SARS-associated coronavirus (SCV) and hepatitis C virus (HCV).
}}
Pour générer des pages wiki
HfdIndexSelect -h $EXPLOR_AREA/Data/Ncbi/Merge/RBID.i -Sk "pubmed:22297745" \
| HfdSelect -Kh $EXPLOR_AREA/Data/Ncbi/Merge/biblio.hfd \
| NlmPubMed2Wicri -a SrasV1
| This area was generated with Dilib version V0.6.33. |  |