Identification and structure-based optimization of novel dihydropyrones as potent HCV RNA polymerase inhibitors.
Identifieur interne : 002161 ( PubMed/Checkpoint ); précédent : 002160; suivant : 002162Identification and structure-based optimization of novel dihydropyrones as potent HCV RNA polymerase inhibitors.
Auteurs : Hui Li [États-Unis] ; John Tatlock ; Angelica Linton ; Javier Gonzalez ; Allen Borchardt ; Peter Dragovich ; Tanya Jewell ; Tom Prins ; Ru Zhou ; Julie Blazel ; Hans Parge ; Robert Love ; Michael Hickey ; Chau Doan ; Stephanie Shi ; Rohit Duggal ; Cristina Lewis ; Shella FuhrmanSource :
- Bioorganic & medicinal chemistry letters [ 0960-894X ] ; 2006.
Descripteurs français
- KwdFr :
- Concentration inhibitrice 50, Cristallographie aux rayons X, DNA-directed RNA polymerases (), DNA-directed RNA polymerases (antagonistes et inhibiteurs), DNA-directed RNA polymerases (métabolisme), Hepacivirus (), Hepacivirus (enzymologie), Hydrogène (), Modèles moléculaires, Protéines virales non structurales (), Pyrones (), Pyrones (pharmacologie), Pyrones (synthèse chimique), RNA replicase (), RNA replicase (antagonistes et inhibiteurs), Relation structure-activité, Structure moléculaire.
- MESH :
- antagonistes et inhibiteurs : DNA-directed RNA polymerases, RNA replicase.
- enzymologie : Hepacivirus.
- métabolisme : DNA-directed RNA polymerases.
- pharmacologie : Pyrones.
- synthèse chimique : Pyrones.
- Concentration inhibitrice 50, Cristallographie aux rayons X, DNA-directed RNA polymerases, Hepacivirus, Hydrogène, Modèles moléculaires, Protéines virales non structurales, Pyrones, RNA replicase, Relation structure-activité, Structure moléculaire.
English descriptors
- KwdEn :
- Crystallography, X-Ray, DNA-Directed RNA Polymerases (antagonists & inhibitors), DNA-Directed RNA Polymerases (chemistry), DNA-Directed RNA Polymerases (metabolism), Hepacivirus (drug effects), Hepacivirus (enzymology), Hydrogen (chemistry), Inhibitory Concentration 50, Models, Molecular, Molecular Structure, Pyrones (chemical synthesis), Pyrones (chemistry), Pyrones (pharmacology), RNA Replicase (antagonists & inhibitors), RNA Replicase (chemistry), Structure-Activity Relationship, Viral Nonstructural Proteins (chemistry).
- MESH :
- chemical , antagonists & inhibitors : DNA-Directed RNA Polymerases, RNA Replicase.
- chemical , chemical synthesis : Pyrones.
- chemical , chemistry : DNA-Directed RNA Polymerases, Hydrogen, Pyrones, RNA Replicase, Viral Nonstructural Proteins.
- chemical , metabolism : DNA-Directed RNA Polymerases.
- drug effects : Hepacivirus.
- enzymology : Hepacivirus.
- chemical , pharmacology : Pyrones.
- Crystallography, X-Ray, Inhibitory Concentration 50, Models, Molecular, Molecular Structure, Structure-Activity Relationship.
Abstract
A novel class of non-nucleoside HCV NS5B polymerase inhibitors has been identified from screening. A co-crystal structure revealed an allosteric binding site in the protein that required a unique conformational change to accommodate inhibitor binding. Herein we report the structure-activity relationships (SARs) of this novel class of dihydropyrone-containing compounds that show potent inhibitory activities against the HCV RNA polymerase in biochemical assays.
DOI: 10.1016/j.bmcl.2006.06.065
PubMed: 16824756
Affiliations:
Links toward previous steps (curation, corpus...)
Links to Exploration step
pubmed:16824756Le document en format XML
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Hui" uniqKey="Li H" first="Hui" last="Li">Hui Li</name><affiliation wicri:level="2"><nlm:affiliation>Pfizer Global Research and Development, La Jolla Laboratories, 10770 Science Center Dr., San Diego, CA 92121, USA. hui.li@pfizer.com</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>Pfizer Global Research and Development, La Jolla Laboratories, 10770 Science Center Dr., San Diego, CA 92121</wicri:regionArea><placeName><region type="state">Californie</region></placeName></affiliation></author><author><name sortKey="Tatlock, John" sort="Tatlock, John" uniqKey="Tatlock J" first="John" last="Tatlock">John Tatlock</name></author><author><name sortKey="Linton, Angelica" sort="Linton, Angelica" uniqKey="Linton A" first="Angelica" last="Linton">Angelica Linton</name></author><author><name sortKey="Gonzalez, Javier" sort="Gonzalez, Javier" uniqKey="Gonzalez J" first="Javier" last="Gonzalez">Javier Gonzalez</name></author><author><name sortKey="Borchardt, Allen" sort="Borchardt, Allen" uniqKey="Borchardt A" first="Allen" last="Borchardt">Allen Borchardt</name></author><author><name sortKey="Dragovich, Peter" sort="Dragovich, Peter" uniqKey="Dragovich P" first="Peter" last="Dragovich">Peter Dragovich</name></author><author><name sortKey="Jewell, Tanya" sort="Jewell, Tanya" uniqKey="Jewell T" first="Tanya" last="Jewell">Tanya Jewell</name></author><author><name sortKey="Prins, Tom" sort="Prins, Tom" uniqKey="Prins T" first="Tom" last="Prins">Tom Prins</name></author><author><name sortKey="Zhou, Ru" sort="Zhou, Ru" uniqKey="Zhou R" first="Ru" last="Zhou">Ru Zhou</name></author><author><name sortKey="Blazel, Julie" sort="Blazel, Julie" uniqKey="Blazel J" first="Julie" last="Blazel">Julie Blazel</name></author><author><name sortKey="Parge, Hans" sort="Parge, Hans" uniqKey="Parge H" first="Hans" last="Parge">Hans Parge</name></author><author><name sortKey="Love, Robert" sort="Love, Robert" uniqKey="Love R" first="Robert" last="Love">Robert 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type="published">2006</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Crystallography, X-Ray</term><term>DNA-Directed RNA Polymerases (antagonists & inhibitors)</term><term>DNA-Directed RNA Polymerases (chemistry)</term><term>DNA-Directed RNA Polymerases (metabolism)</term><term>Hepacivirus (drug effects)</term><term>Hepacivirus (enzymology)</term><term>Hydrogen (chemistry)</term><term>Inhibitory Concentration 50</term><term>Models, Molecular</term><term>Molecular Structure</term><term>Pyrones (chemical synthesis)</term><term>Pyrones (chemistry)</term><term>Pyrones (pharmacology)</term><term>RNA Replicase (antagonists & inhibitors)</term><term>RNA Replicase (chemistry)</term><term>Structure-Activity Relationship</term><term>Viral Nonstructural Proteins (chemistry)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Concentration inhibitrice 50</term><term>Cristallographie aux rayons X</term><term>DNA-directed RNA polymerases ()</term><term>DNA-directed RNA polymerases (antagonistes et inhibiteurs)</term><term>DNA-directed RNA polymerases (métabolisme)</term><term>Hepacivirus ()</term><term>Hepacivirus (enzymologie)</term><term>Hydrogène ()</term><term>Modèles moléculaires</term><term>Protéines virales non structurales ()</term><term>Pyrones ()</term><term>Pyrones (pharmacologie)</term><term>Pyrones (synthèse chimique)</term><term>RNA replicase ()</term><term>RNA replicase (antagonistes et inhibiteurs)</term><term>Relation structure-activité</term><term>Structure moléculaire</term></keywords><keywords scheme="MESH" type="chemical" qualifier="antagonists & inhibitors" xml:lang="en"><term>DNA-Directed RNA Polymerases</term><term>RNA Replicase</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Pyrones</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>DNA-Directed RNA Polymerases</term><term>Hydrogen</term><term>Pyrones</term><term>RNA Replicase</term><term>Viral Nonstructural Proteins</term></keywords><keywords scheme="MESH" type="chemical" qualifier="metabolism" xml:lang="en"><term>DNA-Directed RNA Polymerases</term></keywords><keywords scheme="MESH" qualifier="antagonistes et inhibiteurs" xml:lang="fr"><term>DNA-directed RNA polymerases</term><term>RNA replicase</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Hepacivirus</term></keywords><keywords scheme="MESH" qualifier="enzymologie" xml:lang="fr"><term>Hepacivirus</term></keywords><keywords scheme="MESH" qualifier="enzymology" xml:lang="en"><term>Hepacivirus</term></keywords><keywords scheme="MESH" qualifier="métabolisme" xml:lang="fr"><term>DNA-directed RNA polymerases</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Pyrones</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Pyrones</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Pyrones</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Crystallography, X-Ray</term><term>Inhibitory Concentration 50</term><term>Models, Molecular</term><term>Molecular Structure</term><term>Structure-Activity Relationship</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Concentration inhibitrice 50</term><term>Cristallographie aux rayons X</term><term>DNA-directed RNA polymerases</term><term>Hepacivirus</term><term>Hydrogène</term><term>Modèles moléculaires</term><term>Protéines virales non structurales</term><term>Pyrones</term><term>RNA replicase</term><term>Relation structure-activité</term><term>Structure moléculaire</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">A novel class of non-nucleoside HCV NS5B polymerase inhibitors has been identified from screening. A co-crystal structure revealed an allosteric binding site in the protein that required a unique conformational change to accommodate inhibitor binding. Herein we report the structure-activity relationships (SARs) of this novel class of dihydropyrone-containing compounds that show potent inhibitory activities against the HCV RNA polymerase in biochemical assays.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">16824756</PMID><DateCompleted><Year>2006</Year><Month>10</Month><Day>16</Day></DateCompleted><DateRevised><Year>2013</Year><Month>11</Month><Day>21</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Print">0960-894X</ISSN><JournalIssue CitedMedium="Print"><Volume>16</Volume><Issue>18</Issue><PubDate><Year>2006</Year><Month>Sep</Month><Day>15</Day></PubDate></JournalIssue><Title>Bioorganic & medicinal chemistry letters</Title><ISOAbbreviation>Bioorg. Med. Chem. Lett.</ISOAbbreviation></Journal><ArticleTitle>Identification and structure-based optimization of novel dihydropyrones as potent HCV RNA polymerase inhibitors.</ArticleTitle><Pagination><MedlinePgn>4834-8</MedlinePgn></Pagination><Abstract><AbstractText>A novel class of non-nucleoside HCV NS5B polymerase inhibitors has been identified from screening. A co-crystal structure revealed an allosteric binding site in the protein that required a unique conformational change to accommodate inhibitor binding. Herein we report the structure-activity relationships (SARs) of this novel class of dihydropyrone-containing compounds that show potent inhibitory activities against the HCV RNA polymerase in biochemical assays.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Li</LastName><ForeName>Hui</ForeName><Initials>H</Initials><AffiliationInfo><Affiliation>Pfizer Global Research and Development, La Jolla Laboratories, 10770 Science Center Dr., San Diego, CA 92121, USA. hui.li@pfizer.com</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Tatlock</LastName><ForeName>John</ForeName><Initials>J</Initials></Author><Author ValidYN="Y"><LastName>Linton</LastName><ForeName>Angelica</ForeName><Initials>A</Initials></Author><Author ValidYN="Y"><LastName>Gonzalez</LastName><ForeName>Javier</ForeName><Initials>J</Initials></Author><Author ValidYN="Y"><LastName>Borchardt</LastName><ForeName>Allen</ForeName><Initials>A</Initials></Author><Author ValidYN="Y"><LastName>Dragovich</LastName><ForeName>Peter</ForeName><Initials>P</Initials></Author><Author ValidYN="Y"><LastName>Jewell</LastName><ForeName>Tanya</ForeName><Initials>T</Initials></Author><Author ValidYN="Y"><LastName>Prins</LastName><ForeName>Tom</ForeName><Initials>T</Initials></Author><Author ValidYN="Y"><LastName>Zhou</LastName><ForeName>Ru</ForeName><Initials>R</Initials></Author><Author ValidYN="Y"><LastName>Blazel</LastName><ForeName>Julie</ForeName><Initials>J</Initials></Author><Author ValidYN="Y"><LastName>Parge</LastName><ForeName>Hans</ForeName><Initials>H</Initials></Author><Author ValidYN="Y"><LastName>Love</LastName><ForeName>Robert</ForeName><Initials>R</Initials></Author><Author ValidYN="Y"><LastName>Hickey</LastName><ForeName>Michael</ForeName><Initials>M</Initials></Author><Author ValidYN="Y"><LastName>Doan</LastName><ForeName>Chau</ForeName><Initials>C</Initials></Author><Author ValidYN="Y"><LastName>Shi</LastName><ForeName>Stephanie</ForeName><Initials>S</Initials></Author><Author ValidYN="Y"><LastName>Duggal</LastName><ForeName>Rohit</ForeName><Initials>R</Initials></Author><Author ValidYN="Y"><LastName>Lewis</LastName><ForeName>Cristina</ForeName><Initials>C</Initials></Author><Author ValidYN="Y"><LastName>Fuhrman</LastName><ForeName>Shella</ForeName><Initials>S</Initials></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2006</Year><Month>07</Month><Day>07</Day></ArticleDate></Article><MedlineJournalInfo><Country>England</Country><MedlineTA>Bioorg Med Chem Lett</MedlineTA><NlmUniqueID>9107377</NlmUniqueID><ISSNLinking>0960-894X</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="C087036">NS-5 protein, hepatitis C virus</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D011753">Pyrones</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D017361">Viral Nonstructural Proteins</NameOfSubstance></Chemical><Chemical><RegistryNumber>7YNJ3PO35Z</RegistryNumber><NameOfSubstance UI="D006859">Hydrogen</NameOfSubstance></Chemical><Chemical><RegistryNumber>EC 2.7.7.48</RegistryNumber><NameOfSubstance UI="D012324">RNA Replicase</NameOfSubstance></Chemical><Chemical><RegistryNumber>EC 2.7.7.6</RegistryNumber><NameOfSubstance UI="D012321">DNA-Directed RNA Polymerases</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D018360" MajorTopicYN="N">Crystallography, X-Ray</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D012321" MajorTopicYN="N">DNA-Directed RNA Polymerases</DescriptorName><QualifierName UI="Q000037" MajorTopicYN="Y">antagonists & inhibitors</QualifierName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D016174" MajorTopicYN="N">Hepacivirus</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="Y">drug effects</QualifierName><QualifierName UI="Q000201" MajorTopicYN="Y">enzymology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D006859" MajorTopicYN="N">Hydrogen</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D020128" MajorTopicYN="N">Inhibitory Concentration 50</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D008958" MajorTopicYN="N">Models, Molecular</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D015394" MajorTopicYN="N">Molecular Structure</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D011753" MajorTopicYN="N">Pyrones</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="N">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D012324" MajorTopicYN="N">RNA Replicase</DescriptorName><QualifierName UI="Q000037" MajorTopicYN="N">antagonists & inhibitors</QualifierName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D013329" MajorTopicYN="N">Structure-Activity Relationship</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D017361" MajorTopicYN="N">Viral Nonstructural Proteins</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2006</Year><Month>04</Month><Day>14</Day></PubMedPubDate><PubMedPubDate PubStatus="revised"><Year>2006</Year><Month>06</Month><Day>17</Day></PubMedPubDate><PubMedPubDate PubStatus="accepted"><Year>2006</Year><Month>06</Month><Day>19</Day></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2006</Year><Month>7</Month><Day>11</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2006</Year><Month>10</Month><Day>17</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2006</Year><Month>7</Month><Day>11</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">16824756</ArticleId><ArticleId IdType="pii">S0960-894X(06)00730-X</ArticleId><ArticleId IdType="doi">10.1016/j.bmcl.2006.06.065</ArticleId></ArticleIdList></PubmedData></pubmed><affiliations><list><country><li>États-Unis</li></country><region><li>Californie</li></region></list><tree><noCountry><name sortKey="Blazel, Julie" sort="Blazel, Julie" uniqKey="Blazel J" first="Julie" last="Blazel">Julie Blazel</name><name sortKey="Borchardt, Allen" sort="Borchardt, Allen" uniqKey="Borchardt A" first="Allen" last="Borchardt">Allen Borchardt</name><name sortKey="Doan, Chau" sort="Doan, Chau" uniqKey="Doan C" first="Chau" last="Doan">Chau Doan</name><name sortKey="Dragovich, Peter" sort="Dragovich, Peter" uniqKey="Dragovich P" first="Peter" last="Dragovich">Peter Dragovich</name><name sortKey="Duggal, Rohit" sort="Duggal, Rohit" uniqKey="Duggal R" first="Rohit" last="Duggal">Rohit Duggal</name><name sortKey="Fuhrman, Shella" sort="Fuhrman, Shella" uniqKey="Fuhrman S" first="Shella" last="Fuhrman">Shella Fuhrman</name><name sortKey="Gonzalez, Javier" sort="Gonzalez, Javier" uniqKey="Gonzalez J" first="Javier" last="Gonzalez">Javier Gonzalez</name><name sortKey="Hickey, Michael" sort="Hickey, Michael" uniqKey="Hickey M" first="Michael" last="Hickey">Michael Hickey</name><name sortKey="Jewell, Tanya" sort="Jewell, Tanya" uniqKey="Jewell T" first="Tanya" last="Jewell">Tanya Jewell</name><name sortKey="Lewis, Cristina" sort="Lewis, Cristina" uniqKey="Lewis C" first="Cristina" last="Lewis">Cristina Lewis</name><name sortKey="Linton, Angelica" sort="Linton, Angelica" uniqKey="Linton A" first="Angelica" last="Linton">Angelica Linton</name><name sortKey="Love, Robert" sort="Love, Robert" uniqKey="Love R" first="Robert" last="Love">Robert Love</name><name sortKey="Parge, Hans" sort="Parge, Hans" uniqKey="Parge H" first="Hans" last="Parge">Hans Parge</name><name sortKey="Prins, Tom" sort="Prins, Tom" uniqKey="Prins T" first="Tom" last="Prins">Tom Prins</name><name sortKey="Shi, Stephanie" sort="Shi, Stephanie" uniqKey="Shi S" first="Stephanie" last="Shi">Stephanie Shi</name><name sortKey="Tatlock, John" sort="Tatlock, John" uniqKey="Tatlock J" first="John" last="Tatlock">John Tatlock</name><name sortKey="Zhou, Ru" sort="Zhou, Ru" uniqKey="Zhou R" first="Ru" last="Zhou">Ru Zhou</name></noCountry><country name="États-Unis"><region name="Californie"><name sortKey="Li, Hui" sort="Li, Hui" uniqKey="Li H" first="Hui" last="Li">Hui Li</name></region></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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