Synthesis of cyclopentenyl carbocyclic nucleosides as potential antiviral agents against orthopoxviruses and SARS.
Identifieur interne : 001F68 ( PubMed/Checkpoint ); précédent : 001F67; suivant : 001F69Synthesis of cyclopentenyl carbocyclic nucleosides as potential antiviral agents against orthopoxviruses and SARS.
Auteurs : Jong Hyun Cho [États-Unis] ; Dale L. Bernard ; Robert W. Sidwell ; Earl R. Kern ; Chung K. ChuSource :
- Journal of medicinal chemistry [ 0022-2623 ] ; 2006.
Descripteurs français
- KwdFr :
- Antiviraux (pharmacologie), Antiviraux (synthèse chimique), Nucléosides (pharmacologie), Nucléosides (synthèse chimique), Orthopoxvirus (), Relation structure-activité, Ribose (analogues et dérivés), Ribose (pharmacologie), Ribose (synthèse chimique), Stéréoisomérie, Triazoles (pharmacologie), Triazoles (synthèse chimique), Virus du SRAS ().
- MESH :
- analogues et dérivés : Ribose.
- pharmacologie : Antiviraux, Nucléosides, Ribose, Triazoles.
- synthèse chimique : Antiviraux, Nucléosides, Ribose, Triazoles.
- Orthopoxvirus, Relation structure-activité, Stéréoisomérie, Virus du SRAS.
English descriptors
- KwdEn :
- Antiviral Agents (chemical synthesis), Antiviral Agents (pharmacology), Nucleosides (chemical synthesis), Nucleosides (pharmacology), Orthopoxvirus (drug effects), Ribose (analogs & derivatives), Ribose (chemical synthesis), Ribose (pharmacology), SARS Virus (drug effects), Stereoisomerism, Structure-Activity Relationship, Triazoles (chemical synthesis), Triazoles (pharmacology).
- MESH :
- chemical , analogs & derivatives : Ribose.
- chemical , chemical synthesis : Antiviral Agents, Nucleosides, Ribose, Triazoles.
- chemical , pharmacology : Antiviral Agents, Nucleosides, Ribose, Triazoles.
- drug effects : Orthopoxvirus, SARS Virus.
- Stereoisomerism, Structure-Activity Relationship.
Abstract
A practical and convenient methodology for the synthesis of chiral cyclopentenol derivative (+)-12a has been developed as the key intermediate that was utilized for the synthesis of biologically active carbocyclic nucleosides. The selective protection of allylic hydroxyl group followed by the ring-closing metathesis (RCM) reaction with Grubbs catalysts provided (+)-12a on a 10 g scale with 52% overall yield from D-ribose (4). The key intermediate (+)-12a was utilized for the synthesis of unnatural five-membered ring heterocyclic carbocyclic nucleosides. The newly synthesized 1,2,3-triazole analogue (17c) exhibited potent antiviral activity (EC(50) 0.4 microM) against vaccinia virus and moderate activities (EC(50) 39 microM) against cowpox virus and severe acute respiratory syndrome coronavirus (SARSCoV) (EC(50) 47 microM). The 1,2,4-triazole analogue (17a) also exhibited moderate antiviral activity (EC(50) 21 microM) against SARSCoV.
DOI: 10.1021/jm0509750
PubMed: 16451078
Affiliations:
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Sidwell</name></author><author><name sortKey="Kern, Earl R" sort="Kern, Earl R" uniqKey="Kern E" first="Earl R" last="Kern">Earl R. Kern</name></author><author><name sortKey="Chu, Chung K" sort="Chu, Chung K" uniqKey="Chu C" first="Chung K" last="Chu">Chung K. 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Bernard</name></author><author><name sortKey="Sidwell, Robert W" sort="Sidwell, Robert W" uniqKey="Sidwell R" first="Robert W" last="Sidwell">Robert W. Sidwell</name></author><author><name sortKey="Kern, Earl R" sort="Kern, Earl R" uniqKey="Kern E" first="Earl R" last="Kern">Earl R. Kern</name></author><author><name sortKey="Chu, Chung K" sort="Chu, Chung K" uniqKey="Chu C" first="Chung K" last="Chu">Chung K. Chu</name></author></analytic><series><title level="j">Journal of medicinal chemistry</title><idno type="ISSN">0022-2623</idno><imprint><date when="2006" type="published">2006</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>Nucleosides (chemical synthesis)</term><term>Nucleosides (pharmacology)</term><term>Orthopoxvirus (drug effects)</term><term>Ribose (analogs & derivatives)</term><term>Ribose (chemical synthesis)</term><term>Ribose (pharmacology)</term><term>SARS Virus (drug effects)</term><term>Stereoisomerism</term><term>Structure-Activity Relationship</term><term>Triazoles (chemical synthesis)</term><term>Triazoles (pharmacology)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Antiviraux (pharmacologie)</term><term>Antiviraux (synthèse chimique)</term><term>Nucléosides (pharmacologie)</term><term>Nucléosides (synthèse chimique)</term><term>Orthopoxvirus ()</term><term>Relation structure-activité</term><term>Ribose (analogues et dérivés)</term><term>Ribose (pharmacologie)</term><term>Ribose (synthèse chimique)</term><term>Stéréoisomérie</term><term>Triazoles (pharmacologie)</term><term>Triazoles (synthèse chimique)</term><term>Virus du SRAS ()</term></keywords><keywords scheme="MESH" type="chemical" qualifier="analogs & derivatives" xml:lang="en"><term>Ribose</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Antiviral Agents</term><term>Nucleosides</term><term>Ribose</term><term>Triazoles</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Antiviral Agents</term><term>Nucleosides</term><term>Ribose</term><term>Triazoles</term></keywords><keywords scheme="MESH" qualifier="analogues et dérivés" xml:lang="fr"><term>Ribose</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Orthopoxvirus</term><term>SARS Virus</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Antiviraux</term><term>Nucléosides</term><term>Ribose</term><term>Triazoles</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Antiviraux</term><term>Nucléosides</term><term>Ribose</term><term>Triazoles</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Stereoisomerism</term><term>Structure-Activity Relationship</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Orthopoxvirus</term><term>Relation structure-activité</term><term>Stéréoisomérie</term><term>Virus du SRAS</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">A practical and convenient methodology for the synthesis of chiral cyclopentenol derivative (+)-12a has been developed as the key intermediate that was utilized for the synthesis of biologically active carbocyclic nucleosides. The selective protection of allylic hydroxyl group followed by the ring-closing metathesis (RCM) reaction with Grubbs catalysts provided (+)-12a on a 10 g scale with 52% overall yield from D-ribose (4). The key intermediate (+)-12a was utilized for the synthesis of unnatural five-membered ring heterocyclic carbocyclic nucleosides. The newly synthesized 1,2,3-triazole analogue (17c) exhibited potent antiviral activity (EC(50) 0.4 microM) against vaccinia virus and moderate activities (EC(50) 39 microM) against cowpox virus and severe acute respiratory syndrome coronavirus (SARSCoV) (EC(50) 47 microM). The 1,2,4-triazole analogue (17a) also exhibited moderate antiviral activity (EC(50) 21 microM) against SARSCoV.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">16451078</PMID><DateCompleted><Year>2006</Year><Month>03</Month><Day>29</Day></DateCompleted><DateRevised><Year>2013</Year><Month>11</Month><Day>21</Day></DateRevised><Article PubModel="Print"><Journal><ISSN IssnType="Print">0022-2623</ISSN><JournalIssue CitedMedium="Print"><Volume>49</Volume><Issue>3</Issue><PubDate><Year>2006</Year><Month>Feb</Month><Day>09</Day></PubDate></JournalIssue><Title>Journal of medicinal chemistry</Title><ISOAbbreviation>J. Med. Chem.</ISOAbbreviation></Journal><ArticleTitle>Synthesis of cyclopentenyl carbocyclic nucleosides as potential antiviral agents against orthopoxviruses and SARS.</ArticleTitle><Pagination><MedlinePgn>1140-8</MedlinePgn></Pagination><Abstract><AbstractText>A practical and convenient methodology for the synthesis of chiral cyclopentenol derivative (+)-12a has been developed as the key intermediate that was utilized for the synthesis of biologically active carbocyclic nucleosides. The selective protection of allylic hydroxyl group followed by the ring-closing metathesis (RCM) reaction with Grubbs catalysts provided (+)-12a on a 10 g scale with 52% overall yield from D-ribose (4). The key intermediate (+)-12a was utilized for the synthesis of unnatural five-membered ring heterocyclic carbocyclic nucleosides. The newly synthesized 1,2,3-triazole analogue (17c) exhibited potent antiviral activity (EC(50) 0.4 microM) against vaccinia virus and moderate activities (EC(50) 39 microM) against cowpox virus and severe acute respiratory syndrome coronavirus (SARSCoV) (EC(50) 47 microM). The 1,2,4-triazole analogue (17a) also exhibited moderate antiviral activity (EC(50) 21 microM) against SARSCoV.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Cho</LastName><ForeName>Jong Hyun</ForeName><Initials>JH</Initials><AffiliationInfo><Affiliation>The University of Georgia College of Pharmacy, Athens, GA 30602, USA.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Bernard</LastName><ForeName>Dale L</ForeName><Initials>DL</Initials></Author><Author ValidYN="Y"><LastName>Sidwell</LastName><ForeName>Robert W</ForeName><Initials>RW</Initials></Author><Author ValidYN="Y"><LastName>Kern</LastName><ForeName>Earl R</ForeName><Initials>ER</Initials></Author><Author ValidYN="Y"><LastName>Chu</LastName><ForeName>Chung K</ForeName><Initials>CK</Initials></Author></AuthorList><Language>eng</Language><GrantList CompleteYN="Y"><Grant><GrantID>N01 AI 30048</GrantID><Acronym>AI</Acronym><Agency>NIAID NIH HHS</Agency><Country>United States</Country></Grant><Grant><GrantID>N01 AI 30049</GrantID><Acronym>AI</Acronym><Agency>NIAID NIH HHS</Agency><Country>United States</Country></Grant><Grant><GrantID>U019 AI 056540</GrantID><Acronym>AI</Acronym><Agency>NIAID NIH HHS</Agency><Country>United States</Country></Grant></GrantList><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D052061">Research Support, N.I.H., Extramural</PublicationType></PublicationTypeList></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>J Med Chem</MedlineTA><NlmUniqueID>9716531</NlmUniqueID><ISSNLinking>0022-2623</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="C508999">1-(4,5-dihydroxy-3-hydroxymethylcyclopenten-2-enyl)-1H-1,2,3-triazole-4-carboxylic acid amide</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000998">Antiviral Agents</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D009705">Nucleosides</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D014230">Triazoles</NameOfSubstance></Chemical><Chemical><RegistryNumber>681HV46001</RegistryNumber><NameOfSubstance UI="D012266">Ribose</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="N">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D009705" MajorTopicYN="N">Nucleosides</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="Y">chemical synthesis</QualifierName><QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D018155" MajorTopicYN="N">Orthopoxvirus</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="Y">drug effects</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D012266" MajorTopicYN="N">Ribose</DescriptorName><QualifierName UI="Q000031" MajorTopicYN="N">analogs & derivatives</QualifierName><QualifierName UI="Q000138" MajorTopicYN="N">chemical synthesis</QualifierName><QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D045473" MajorTopicYN="N">SARS Virus</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="Y">drug effects</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D013237" MajorTopicYN="N">Stereoisomerism</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D013329" MajorTopicYN="N">Structure-Activity Relationship</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D014230" MajorTopicYN="N">Triazoles</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="Y">chemical synthesis</QualifierName><QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="pubmed"><Year>2006</Year><Month>2</Month><Day>3</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2006</Year><Month>3</Month><Day>30</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2006</Year><Month>2</Month><Day>3</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">16451078</ArticleId><ArticleId IdType="doi">10.1021/jm0509750</ArticleId></ArticleIdList></PubmedData></pubmed><affiliations><list><country><li>États-Unis</li></country><region><li>Géorgie (États-Unis)</li></region></list><tree><noCountry><name sortKey="Bernard, Dale L" sort="Bernard, Dale L" uniqKey="Bernard D" first="Dale L" last="Bernard">Dale L. Bernard</name><name sortKey="Chu, Chung K" sort="Chu, Chung K" uniqKey="Chu C" first="Chung K" last="Chu">Chung K. Chu</name><name sortKey="Kern, Earl R" sort="Kern, Earl R" uniqKey="Kern E" first="Earl R" last="Kern">Earl R. Kern</name><name sortKey="Sidwell, Robert W" sort="Sidwell, Robert W" uniqKey="Sidwell R" first="Robert W" last="Sidwell">Robert W. Sidwell</name></noCountry><country name="États-Unis"><region name="Géorgie (États-Unis)"><name sortKey="Cho, Jong Hyun" sort="Cho, Jong Hyun" uniqKey="Cho J" first="Jong Hyun" last="Cho">Jong Hyun Cho</name></region></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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