Design, synthesis and antiviral efficacy of a series of potent chloropyridyl ester-derived SARS-CoV 3CLpro inhibitors
Identifieur interne : 001D48 ( Ncbi/Merge ); précédent : 001D47; suivant : 001D49Design, synthesis and antiviral efficacy of a series of potent chloropyridyl ester-derived SARS-CoV 3CLpro inhibitors
Auteurs : Arun K. Ghosh [États-Unis] ; Gangli Gong [États-Unis] ; Valerie Grum-Tokars [États-Unis] ; Debbie C. Mulhearn [États-Unis] ; Susan C. Baker [États-Unis] ; Melissa Coughlin [États-Unis] ; Bellur S. Prabhakar [États-Unis] ; Katrina Sleeman [États-Unis] ; Michael E. Johnson [États-Unis] ; Andrew D. Mesecar [États-Unis]Source :
- Bioorganic & Medicinal Chemistry Letters [ 0960-894X ] ; 2008.
Descripteurs français
- KwdFr :
- Animaux, Antiviraux (), Antiviraux (pharmacologie), Antiviraux (synthèse chimique), Chimie pharmaceutique (), Concentration inhibitrice 50, Conception de médicament, Conformation moléculaire, Cysteine endopeptidases (), Domaine catalytique, Esters, Humains, Liaison aux protéines, Modèles chimiques, Modèles moléculaires, Protéines virales (antagonistes et inhibiteurs), Virus du SRAS (métabolisme).
- MESH :
- antagonistes et inhibiteurs : Protéines virales.
- métabolisme : Virus du SRAS.
- pharmacologie : Antiviraux.
- synthèse chimique : Antiviraux.
- Animaux, Antiviraux, Chimie pharmaceutique, Concentration inhibitrice 50, Conception de médicament, Conformation moléculaire, Cysteine endopeptidases, Domaine catalytique, Esters, Humains, Liaison aux protéines, Modèles chimiques, Modèles moléculaires.
English descriptors
- KwdEn :
- Animals, Antiviral Agents (chemical synthesis), Antiviral Agents (chemistry), Antiviral Agents (pharmacology), Catalytic Domain, Chemistry, Pharmaceutical (methods), Cysteine Endopeptidases (chemistry), Drug Design, Esters, Humans, Inhibitory Concentration 50, Models, Chemical, Models, Molecular, Molecular Conformation, Protein Binding, SARS Virus (metabolism), Viral Proteins (antagonists & inhibitors).
- MESH :
- chemical , antagonists & inhibitors : Viral Proteins.
- chemical , chemical synthesis : Antiviral Agents.
- chemical , chemistry : Antiviral Agents, Cysteine Endopeptidases.
- chemical , pharmacology : Antiviral Agents.
- metabolism : SARS Virus.
- methods : Chemistry, Pharmaceutical.
- Animals, Catalytic Domain, Drug Design, Esters, Humans, Inhibitory Concentration 50, Models, Chemical, Models, Molecular, Molecular Conformation, Protein Binding.
Abstract
Design, synthesis and biological evaluation of a series of chloropyridyl ester-derived SARS-CoV 3CLpro Inhibitors are described Inhibitors
Url:
DOI: 10.1016/j.bmcl.2008.08.082
PubMed: 18796354
PubMed Central: 2745596
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PMC:2745596Le document en format XML
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Ghosh</name><affiliation wicri:level="2"><nlm:aff id="aff1">Departments of Chemistry and Medicinal Chemistry, Purdue University, 560 Oval drive, West Lafayette, IN 47907, USA</nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea>Departments of Chemistry and Medicinal Chemistry, Purdue University, 560 Oval drive, West Lafayette, IN 47907</wicri:regionArea><placeName><region type="state">Indiana</region></placeName></affiliation></author><author><name sortKey="Gong, Gangli" sort="Gong, Gangli" uniqKey="Gong G" first="Gangli" last="Gong">Gangli Gong</name><affiliation wicri:level="2"><nlm:aff id="aff1">Departments of Chemistry and Medicinal Chemistry, Purdue University, 560 Oval drive, West Lafayette, IN 47907, USA</nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea>Departments of Chemistry and Medicinal Chemistry, Purdue University, 560 Oval drive, West Lafayette, IN 47907</wicri:regionArea><placeName><region type="state">Indiana</region></placeName></affiliation></author><author><name sortKey="Grum Tokars, Valerie" sort="Grum Tokars, Valerie" uniqKey="Grum Tokars V" first="Valerie" last="Grum-Tokars">Valerie Grum-Tokars</name><affiliation wicri:level="4"><nlm:aff id="aff2">Center for Pharmaceutical Biotechnology, Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, 900 S. Ashland, IL 60607, USA</nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea>Center for Pharmaceutical Biotechnology, Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, 900 S. Ashland, IL 60607</wicri:regionArea><placeName><region type="state">Illinois</region><settlement type="city">Chicago</settlement></placeName><orgName type="university">Université de l'Illinois à Chicago</orgName></affiliation></author><author><name sortKey="Mulhearn, Debbie C" sort="Mulhearn, Debbie C" uniqKey="Mulhearn D" first="Debbie C." last="Mulhearn">Debbie C. Mulhearn</name><affiliation wicri:level="4"><nlm:aff id="aff2">Center for Pharmaceutical Biotechnology, Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, 900 S. Ashland, IL 60607, USA</nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea>Center for Pharmaceutical Biotechnology, Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, 900 S. Ashland, IL 60607</wicri:regionArea><placeName><region type="state">Illinois</region><settlement type="city">Chicago</settlement></placeName><orgName type="university">Université de l'Illinois à Chicago</orgName></affiliation></author><author><name sortKey="Baker, Susan C" sort="Baker, Susan C" uniqKey="Baker S" first="Susan C." last="Baker">Susan C. Baker</name><affiliation wicri:level="4"><nlm:aff id="aff3">Department of Microbiology and Immunology, Loyola University of Chicago, Stritch School of Medicine, Maywood, IL, USA</nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Microbiology and Immunology, Loyola University of Chicago, Stritch School of Medicine, Maywood, IL</wicri:regionArea><placeName><region type="state">Illinois</region><settlement type="city">Chicago</settlement></placeName><orgName type="university">Université de Chicago</orgName></affiliation></author><author><name sortKey="Coughlin, Melissa" sort="Coughlin, Melissa" uniqKey="Coughlin M" first="Melissa" last="Coughlin">Melissa Coughlin</name><affiliation wicri:level="4"><nlm:aff id="aff4">Department of Microbiology and Immunology, University of Illinois at Chicago, IL 60607, USA</nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Microbiology and Immunology, University of Illinois at Chicago, IL 60607</wicri:regionArea><placeName><region type="state">Illinois</region><settlement type="city">Chicago</settlement></placeName><orgName type="university">Université de l'Illinois à Chicago</orgName></affiliation></author><author><name sortKey="Prabhakar, Bellur S" sort="Prabhakar, Bellur S" uniqKey="Prabhakar B" first="Bellur S." last="Prabhakar">Bellur S. Prabhakar</name><affiliation wicri:level="4"><nlm:aff id="aff4">Department of Microbiology and Immunology, University of Illinois at Chicago, IL 60607, USA</nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Microbiology and Immunology, University of Illinois at Chicago, IL 60607</wicri:regionArea><placeName><region type="state">Illinois</region><settlement type="city">Chicago</settlement></placeName><orgName type="university">Université de l'Illinois à Chicago</orgName></affiliation></author><author><name sortKey="Sleeman, Katrina" sort="Sleeman, Katrina" uniqKey="Sleeman K" first="Katrina" last="Sleeman">Katrina Sleeman</name><affiliation wicri:level="4"><nlm:aff id="aff3">Department of Microbiology and Immunology, Loyola University of Chicago, Stritch School of Medicine, Maywood, IL, USA</nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Microbiology and Immunology, Loyola University of Chicago, Stritch School of Medicine, Maywood, IL</wicri:regionArea><placeName><region type="state">Illinois</region><settlement type="city">Chicago</settlement></placeName><orgName type="university">Université de Chicago</orgName></affiliation></author><author><name sortKey="Johnson, Michael E" sort="Johnson, Michael E" uniqKey="Johnson M" first="Michael E." last="Johnson">Michael E. Johnson</name><affiliation wicri:level="4"><nlm:aff id="aff2">Center for Pharmaceutical Biotechnology, Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, 900 S. Ashland, IL 60607, USA</nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea>Center for Pharmaceutical Biotechnology, Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, 900 S. Ashland, IL 60607</wicri:regionArea><placeName><region type="state">Illinois</region><settlement type="city">Chicago</settlement></placeName><orgName type="university">Université de l'Illinois à Chicago</orgName></affiliation></author><author><name sortKey="Mesecar, Andrew D" sort="Mesecar, Andrew D" uniqKey="Mesecar A" first="Andrew D." last="Mesecar">Andrew D. Mesecar</name><affiliation wicri:level="4"><nlm:aff id="aff2">Center for Pharmaceutical Biotechnology, Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, 900 S. Ashland, IL 60607, USA</nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea>Center for Pharmaceutical Biotechnology, Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, 900 S. Ashland, IL 60607</wicri:regionArea><placeName><region type="state">Illinois</region><settlement type="city">Chicago</settlement></placeName><orgName type="university">Université de l'Illinois à Chicago</orgName></affiliation></author></analytic><series><title level="j">Bioorganic & Medicinal Chemistry Letters</title><idno type="ISSN">0960-894X</idno><idno type="eISSN">1464-3405</idno><imprint><date when="2008">2008</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Animals</term><term>Antiviral Agents (chemical synthesis)</term><term>Antiviral Agents (chemistry)</term><term>Antiviral Agents (pharmacology)</term><term>Catalytic Domain</term><term>Chemistry, Pharmaceutical (methods)</term><term>Cysteine Endopeptidases (chemistry)</term><term>Drug Design</term><term>Esters</term><term>Humans</term><term>Inhibitory Concentration 50</term><term>Models, Chemical</term><term>Models, Molecular</term><term>Molecular Conformation</term><term>Protein Binding</term><term>SARS Virus (metabolism)</term><term>Viral Proteins (antagonists & inhibitors)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Animaux</term><term>Antiviraux ()</term><term>Antiviraux (pharmacologie)</term><term>Antiviraux (synthèse chimique)</term><term>Chimie pharmaceutique ()</term><term>Concentration inhibitrice 50</term><term>Conception de médicament</term><term>Conformation moléculaire</term><term>Cysteine endopeptidases ()</term><term>Domaine catalytique</term><term>Esters</term><term>Humains</term><term>Liaison aux protéines</term><term>Modèles chimiques</term><term>Modèles moléculaires</term><term>Protéines virales (antagonistes et inhibiteurs)</term><term>Virus du SRAS (métabolisme)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="antagonists & inhibitors" xml:lang="en"><term>Viral Proteins</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Antiviral Agents</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Antiviral Agents</term><term>Cysteine Endopeptidases</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Antiviral Agents</term></keywords><keywords scheme="MESH" qualifier="antagonistes et inhibiteurs" xml:lang="fr"><term>Protéines virales</term></keywords><keywords scheme="MESH" qualifier="metabolism" xml:lang="en"><term>SARS Virus</term></keywords><keywords scheme="MESH" qualifier="methods" xml:lang="en"><term>Chemistry, Pharmaceutical</term></keywords><keywords scheme="MESH" qualifier="métabolisme" xml:lang="fr"><term>Virus du SRAS</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Antiviraux</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Antiviraux</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Animals</term><term>Catalytic Domain</term><term>Drug Design</term><term>Esters</term><term>Humans</term><term>Inhibitory Concentration 50</term><term>Models, Chemical</term><term>Models, Molecular</term><term>Molecular Conformation</term><term>Protein Binding</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Animaux</term><term>Antiviraux</term><term>Chimie pharmaceutique</term><term>Concentration inhibitrice 50</term><term>Conception de médicament</term><term>Conformation moléculaire</term><term>Cysteine endopeptidases</term><term>Domaine catalytique</term><term>Esters</term><term>Humains</term><term>Liaison aux protéines</term><term>Modèles chimiques</term><term>Modèles moléculaires</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><title>Graphical abstract</title><p>Design, synthesis and biological evaluation of a series of chloropyridyl ester-derived SARS-CoV 3CLpro Inhibitors are described Inhibitors <bold>10</bold> has shown potent activity in both enzyme inhibitory and antiviral assays</p><fig id="d32e1103" position="anchor"><graphic xlink:href="fx1"></graphic></fig></div></front><back><div1 type="bibliography"><listBibl><biblStruct></biblStruct><biblStruct><analytic><author><name sortKey="He, J F" uniqKey="He J">J.-F. He</name></author><author><name sortKey="Peng, G W" uniqKey="Peng G">G.-W. Peng</name></author><author><name sortKey="Min, J" uniqKey="Min J">J. Min</name></author><author><name sortKey="Yu, D W" uniqKey="Yu D">D.-W. Yu</name></author><author><name sortKey="Liang, W L" uniqKey="Liang W">W.-L. Liang</name></author><author><name sortKey="Zhang, S Y" uniqKey="Zhang S">S.-Y. Zhang</name></author><author><name sortKey="Xu, R H" uniqKey="Xu R">R.-H. Xu</name></author><author><name sortKey="Zheng, H Y" uniqKey="Zheng H">H.-Y. Zheng</name></author><author><name sortKey="Wu, X W" uniqKey="Wu X">X.-W. Wu</name></author><author><name sortKey="Xu, J" uniqKey="Xu J">J. Xu</name></author><author><name sortKey="Wang, Z H" uniqKey="Wang Z">Z.-H. Wang</name></author><author><name sortKey="Fang, L" uniqKey="Fang L">L. Fang</name></author><author><name sortKey="Zhang, X" uniqKey="Zhang X">X. Zhang</name></author><author><name sortKey="Li, H" uniqKey="Li H">H. 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Ghosh</name><affiliation wicri:level="2"><nlm:aff id="aff1">Departments of Chemistry and Medicinal Chemistry, Purdue University, 560 Oval drive, West Lafayette, IN 47907, USA</nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea>Departments of Chemistry and Medicinal Chemistry, Purdue University, 560 Oval drive, West Lafayette, IN 47907</wicri:regionArea><placeName><region type="state">Indiana</region></placeName></affiliation></author><author><name sortKey="Gong, Gangli" sort="Gong, Gangli" uniqKey="Gong G" first="Gangli" last="Gong">Gangli Gong</name><affiliation wicri:level="2"><nlm:aff id="aff1">Departments of Chemistry and Medicinal Chemistry, Purdue University, 560 Oval drive, West Lafayette, IN 47907, USA</nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea>Departments of Chemistry and Medicinal Chemistry, Purdue University, 560 Oval drive, West Lafayette, IN 47907</wicri:regionArea><placeName><region type="state">Indiana</region></placeName></affiliation></author><author><name sortKey="Grum Tokars, Valerie" sort="Grum Tokars, Valerie" uniqKey="Grum Tokars V" first="Valerie" last="Grum-Tokars">Valerie Grum-Tokars</name><affiliation wicri:level="4"><nlm:aff id="aff2">Center for Pharmaceutical Biotechnology, Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, 900 S. Ashland, IL 60607, USA</nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea>Center for Pharmaceutical Biotechnology, Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, 900 S. Ashland, IL 60607</wicri:regionArea><placeName><region type="state">Illinois</region><settlement type="city">Chicago</settlement></placeName><orgName type="university">Université de l'Illinois à Chicago</orgName></affiliation></author><author><name sortKey="Mulhearn, Debbie C" sort="Mulhearn, Debbie C" uniqKey="Mulhearn D" first="Debbie C." last="Mulhearn">Debbie C. Mulhearn</name><affiliation wicri:level="4"><nlm:aff id="aff2">Center for Pharmaceutical Biotechnology, Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, 900 S. Ashland, IL 60607, USA</nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea>Center for Pharmaceutical Biotechnology, Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, 900 S. Ashland, IL 60607</wicri:regionArea><placeName><region type="state">Illinois</region><settlement type="city">Chicago</settlement></placeName><orgName type="university">Université de l'Illinois à Chicago</orgName></affiliation></author><author><name sortKey="Baker, Susan C" sort="Baker, Susan C" uniqKey="Baker S" first="Susan C." last="Baker">Susan C. Baker</name><affiliation wicri:level="4"><nlm:aff id="aff3">Department of Microbiology and Immunology, Loyola University of Chicago, Stritch School of Medicine, Maywood, IL, USA</nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Microbiology and Immunology, Loyola University of Chicago, Stritch School of Medicine, Maywood, IL</wicri:regionArea><placeName><region type="state">Illinois</region><settlement type="city">Chicago</settlement></placeName><orgName type="university">Université de Chicago</orgName></affiliation></author><author><name sortKey="Coughlin, Melissa" sort="Coughlin, Melissa" uniqKey="Coughlin M" first="Melissa" last="Coughlin">Melissa Coughlin</name><affiliation wicri:level="4"><nlm:aff id="aff4">Department of Microbiology and Immunology, University of Illinois at Chicago, IL 60607, USA</nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Microbiology and Immunology, University of Illinois at Chicago, IL 60607</wicri:regionArea><placeName><region type="state">Illinois</region><settlement type="city">Chicago</settlement></placeName><orgName type="university">Université de l'Illinois à Chicago</orgName></affiliation></author><author><name sortKey="Prabhakar, Bellur S" sort="Prabhakar, Bellur S" uniqKey="Prabhakar B" first="Bellur S." last="Prabhakar">Bellur S. Prabhakar</name><affiliation wicri:level="4"><nlm:aff id="aff4">Department of Microbiology and Immunology, University of Illinois at Chicago, IL 60607, USA</nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Microbiology and Immunology, University of Illinois at Chicago, IL 60607</wicri:regionArea><placeName><region type="state">Illinois</region><settlement type="city">Chicago</settlement></placeName><orgName type="university">Université de l'Illinois à Chicago</orgName></affiliation></author><author><name sortKey="Sleeman, Katrina" sort="Sleeman, Katrina" uniqKey="Sleeman K" first="Katrina" last="Sleeman">Katrina Sleeman</name><affiliation wicri:level="4"><nlm:aff id="aff3">Department of Microbiology and Immunology, Loyola University of Chicago, Stritch School of Medicine, Maywood, IL, USA</nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Microbiology and Immunology, Loyola University of Chicago, Stritch School of Medicine, Maywood, IL</wicri:regionArea><placeName><region type="state">Illinois</region><settlement type="city">Chicago</settlement></placeName><orgName type="university">Université de Chicago</orgName></affiliation></author><author><name sortKey="Johnson, Michael E" sort="Johnson, Michael E" uniqKey="Johnson M" first="Michael E." last="Johnson">Michael E. Johnson</name><affiliation wicri:level="4"><nlm:aff id="aff2">Center for Pharmaceutical Biotechnology, Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, 900 S. Ashland, IL 60607, USA</nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea>Center for Pharmaceutical Biotechnology, Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, 900 S. Ashland, IL 60607</wicri:regionArea><placeName><region type="state">Illinois</region><settlement type="city">Chicago</settlement></placeName><orgName type="university">Université de l'Illinois à Chicago</orgName></affiliation></author><author><name sortKey="Mesecar, Andrew D" sort="Mesecar, Andrew D" uniqKey="Mesecar A" first="Andrew D." last="Mesecar">Andrew D. Mesecar</name><affiliation wicri:level="4"><nlm:aff id="aff2">Center for Pharmaceutical Biotechnology, Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, 900 S. Ashland, IL 60607, USA</nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea>Center for Pharmaceutical Biotechnology, Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, 900 S. Ashland, IL 60607</wicri:regionArea><placeName><region type="state">Illinois</region><settlement type="city">Chicago</settlement></placeName><orgName type="university">Université de l'Illinois à Chicago</orgName></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">18796354</idno><idno type="pmc">2745596</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2745596</idno><idno type="RBID">PMC:2745596</idno><idno type="doi">10.1016/j.bmcl.2008.08.082</idno><date when="2008">2008</date><idno type="wicri:Area/Pmc/Corpus">000834</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000834</idno><idno type="wicri:Area/Pmc/Curation">000834</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Curation">000834</idno><idno type="wicri:Area/Pmc/Checkpoint">000E31</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Checkpoint">000E31</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Design, synthesis and antiviral efficacy of a series of potent chloropyridyl ester-derived SARS-CoV 3CLpro inhibitors</title><author><name sortKey="Ghosh, Arun K" sort="Ghosh, Arun K" uniqKey="Ghosh A" first="Arun K." last="Ghosh">Arun K. Ghosh</name><affiliation wicri:level="2"><nlm:aff id="aff1">Departments of Chemistry and Medicinal Chemistry, Purdue University, 560 Oval drive, West Lafayette, IN 47907, USA</nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea>Departments of Chemistry and Medicinal Chemistry, Purdue University, 560 Oval drive, West Lafayette, IN 47907</wicri:regionArea><placeName><region type="state">Indiana</region></placeName></affiliation></author><author><name sortKey="Gong, Gangli" sort="Gong, Gangli" uniqKey="Gong G" first="Gangli" last="Gong">Gangli Gong</name><affiliation wicri:level="2"><nlm:aff id="aff1">Departments of Chemistry and Medicinal Chemistry, Purdue University, 560 Oval drive, West Lafayette, IN 47907, USA</nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea>Departments of Chemistry and Medicinal Chemistry, Purdue University, 560 Oval drive, West Lafayette, IN 47907</wicri:regionArea><placeName><region type="state">Indiana</region></placeName></affiliation></author><author><name sortKey="Grum Tokars, Valerie" sort="Grum Tokars, Valerie" uniqKey="Grum Tokars V" first="Valerie" last="Grum-Tokars">Valerie Grum-Tokars</name><affiliation wicri:level="4"><nlm:aff id="aff2">Center for Pharmaceutical Biotechnology, Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, 900 S. Ashland, IL 60607, USA</nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea>Center for Pharmaceutical Biotechnology, Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, 900 S. Ashland, IL 60607</wicri:regionArea><placeName><region type="state">Illinois</region><settlement type="city">Chicago</settlement></placeName><orgName type="university">Université de l'Illinois à Chicago</orgName></affiliation></author><author><name sortKey="Mulhearn, Debbie C" sort="Mulhearn, Debbie C" uniqKey="Mulhearn D" first="Debbie C." last="Mulhearn">Debbie C. Mulhearn</name><affiliation wicri:level="4"><nlm:aff id="aff2">Center for Pharmaceutical Biotechnology, Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, 900 S. Ashland, IL 60607, USA</nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea>Center for Pharmaceutical Biotechnology, Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, 900 S. Ashland, IL 60607</wicri:regionArea><placeName><region type="state">Illinois</region><settlement type="city">Chicago</settlement></placeName><orgName type="university">Université de l'Illinois à Chicago</orgName></affiliation></author><author><name sortKey="Baker, Susan C" sort="Baker, Susan C" uniqKey="Baker S" first="Susan C." last="Baker">Susan C. Baker</name><affiliation wicri:level="4"><nlm:aff id="aff3">Department of Microbiology and Immunology, Loyola University of Chicago, Stritch School of Medicine, Maywood, IL, USA</nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Microbiology and Immunology, Loyola University of Chicago, Stritch School of Medicine, Maywood, IL</wicri:regionArea><placeName><region type="state">Illinois</region><settlement type="city">Chicago</settlement></placeName><orgName type="university">Université de Chicago</orgName></affiliation></author><author><name sortKey="Coughlin, Melissa" sort="Coughlin, Melissa" uniqKey="Coughlin M" first="Melissa" last="Coughlin">Melissa Coughlin</name><affiliation wicri:level="4"><nlm:aff id="aff4">Department of Microbiology and Immunology, University of Illinois at Chicago, IL 60607, USA</nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Microbiology and Immunology, University of Illinois at Chicago, IL 60607</wicri:regionArea><placeName><region type="state">Illinois</region><settlement type="city">Chicago</settlement></placeName><orgName type="university">Université de l'Illinois à Chicago</orgName></affiliation></author><author><name sortKey="Prabhakar, Bellur S" sort="Prabhakar, Bellur S" uniqKey="Prabhakar B" first="Bellur S." last="Prabhakar">Bellur S. Prabhakar</name><affiliation wicri:level="4"><nlm:aff id="aff4">Department of Microbiology and Immunology, University of Illinois at Chicago, IL 60607, USA</nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Microbiology and Immunology, University of Illinois at Chicago, IL 60607</wicri:regionArea><placeName><region type="state">Illinois</region><settlement type="city">Chicago</settlement></placeName><orgName type="university">Université de l'Illinois à Chicago</orgName></affiliation></author><author><name sortKey="Sleeman, Katrina" sort="Sleeman, Katrina" uniqKey="Sleeman K" first="Katrina" last="Sleeman">Katrina Sleeman</name><affiliation wicri:level="4"><nlm:aff id="aff3">Department of Microbiology and Immunology, Loyola University of Chicago, Stritch School of Medicine, Maywood, IL, USA</nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Microbiology and Immunology, Loyola University of Chicago, Stritch School of Medicine, Maywood, IL</wicri:regionArea><placeName><region type="state">Illinois</region><settlement type="city">Chicago</settlement></placeName><orgName type="university">Université de Chicago</orgName></affiliation></author><author><name sortKey="Johnson, Michael E" sort="Johnson, Michael E" uniqKey="Johnson M" first="Michael E." last="Johnson">Michael E. Johnson</name><affiliation wicri:level="4"><nlm:aff id="aff2">Center for Pharmaceutical Biotechnology, Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, 900 S. Ashland, IL 60607, USA</nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea>Center for Pharmaceutical Biotechnology, Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, 900 S. Ashland, IL 60607</wicri:regionArea><placeName><region type="state">Illinois</region><settlement type="city">Chicago</settlement></placeName><orgName type="university">Université de l'Illinois à Chicago</orgName></affiliation></author><author><name sortKey="Mesecar, Andrew D" sort="Mesecar, Andrew D" uniqKey="Mesecar A" first="Andrew D." last="Mesecar">Andrew D. Mesecar</name><affiliation wicri:level="4"><nlm:aff id="aff2">Center for Pharmaceutical Biotechnology, Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, 900 S. Ashland, IL 60607, USA</nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea>Center for Pharmaceutical Biotechnology, Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, 900 S. Ashland, IL 60607</wicri:regionArea><placeName><region type="state">Illinois</region><settlement type="city">Chicago</settlement></placeName><orgName type="university">Université de l'Illinois à Chicago</orgName></affiliation></author></analytic><series><title level="j">Bioorganic & Medicinal Chemistry Letters</title><idno type="ISSN">0960-894X</idno><idno type="eISSN">1464-3405</idno><imprint><date when="2008">2008</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><title>Graphical abstract</title><p>Design, synthesis and biological evaluation of a series of chloropyridyl ester-derived SARS-CoV 3CLpro Inhibitors are described Inhibitors <bold>10</bold> has shown potent activity in both enzyme inhibitory and antiviral assays</p><fig id="d32e1103" position="anchor"><graphic xlink:href="fx1"></graphic></fig></div></front><back><div1 type="bibliography"><listBibl><biblStruct></biblStruct><biblStruct><analytic><author><name sortKey="He, J F" uniqKey="He J">J.-F. 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Ghosh</name><affiliation wicri:level="2"><nlm:affiliation>Department of Chemistry, Purdue University, 560 Oval drive, West Lafayette, IN 47907, USA. akghosh@purdue.edu</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Chemistry, Purdue University, 560 Oval drive, West Lafayette, IN 47907</wicri:regionArea><placeName><region type="state">Indiana</region></placeName></affiliation></author><author><name sortKey="Gong, Gangli" sort="Gong, Gangli" uniqKey="Gong G" first="Gangli" last="Gong">Gangli Gong</name></author><author><name sortKey="Grum Tokars, Valerie" sort="Grum Tokars, Valerie" uniqKey="Grum Tokars V" first="Valerie" last="Grum-Tokars">Valerie Grum-Tokars</name></author><author><name sortKey="Mulhearn, Debbie C" sort="Mulhearn, Debbie C" uniqKey="Mulhearn D" first="Debbie C" last="Mulhearn">Debbie C. Mulhearn</name></author><author><name sortKey="Baker, Susan C" sort="Baker, Susan C" uniqKey="Baker S" first="Susan C" last="Baker">Susan C. Baker</name></author><author><name sortKey="Coughlin, Melissa" sort="Coughlin, Melissa" uniqKey="Coughlin M" first="Melissa" last="Coughlin">Melissa Coughlin</name></author><author><name sortKey="Prabhakar, Bellur S" sort="Prabhakar, Bellur S" uniqKey="Prabhakar B" first="Bellur S" last="Prabhakar">Bellur S. Prabhakar</name></author><author><name sortKey="Sleeman, Katrina" sort="Sleeman, Katrina" uniqKey="Sleeman K" first="Katrina" last="Sleeman">Katrina Sleeman</name></author><author><name sortKey="Johnson, Michael E" sort="Johnson, Michael E" uniqKey="Johnson M" first="Michael E" last="Johnson">Michael E. Johnson</name></author><author><name sortKey="Mesecar, Andrew D" sort="Mesecar, Andrew D" uniqKey="Mesecar A" first="Andrew D" last="Mesecar">Andrew D. Mesecar</name></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2008">2008</date><idno type="RBID">pubmed:18796354</idno><idno type="pmid">18796354</idno><idno type="doi">10.1016/j.bmcl.2008.08.082</idno><idno type="wicri:Area/PubMed/Corpus">001A67</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">001A67</idno><idno type="wicri:Area/PubMed/Curation">001A67</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Curation">001A67</idno><idno type="wicri:Area/PubMed/Checkpoint">001B59</idno><idno type="wicri:explorRef" wicri:stream="Checkpoint" wicri:step="PubMed">001B59</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Design, synthesis and antiviral efficacy of a series of potent chloropyridyl ester-derived SARS-CoV 3CLpro inhibitors.</title><author><name sortKey="Ghosh, Arun K" sort="Ghosh, Arun K" uniqKey="Ghosh A" first="Arun K" last="Ghosh">Arun K. Ghosh</name><affiliation wicri:level="2"><nlm:affiliation>Department of Chemistry, Purdue University, 560 Oval drive, West Lafayette, IN 47907, USA. akghosh@purdue.edu</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Chemistry, Purdue University, 560 Oval drive, West Lafayette, IN 47907</wicri:regionArea><placeName><region type="state">Indiana</region></placeName></affiliation></author><author><name sortKey="Gong, Gangli" sort="Gong, Gangli" uniqKey="Gong G" first="Gangli" last="Gong">Gangli Gong</name></author><author><name sortKey="Grum Tokars, Valerie" sort="Grum Tokars, Valerie" uniqKey="Grum Tokars V" first="Valerie" last="Grum-Tokars">Valerie Grum-Tokars</name></author><author><name sortKey="Mulhearn, Debbie C" sort="Mulhearn, Debbie C" uniqKey="Mulhearn D" first="Debbie C" last="Mulhearn">Debbie C. Mulhearn</name></author><author><name sortKey="Baker, Susan C" sort="Baker, Susan C" uniqKey="Baker S" first="Susan C" last="Baker">Susan C. Baker</name></author><author><name sortKey="Coughlin, Melissa" sort="Coughlin, Melissa" uniqKey="Coughlin M" first="Melissa" last="Coughlin">Melissa Coughlin</name></author><author><name sortKey="Prabhakar, Bellur S" sort="Prabhakar, Bellur S" uniqKey="Prabhakar B" first="Bellur S" last="Prabhakar">Bellur S. Prabhakar</name></author><author><name sortKey="Sleeman, Katrina" sort="Sleeman, Katrina" uniqKey="Sleeman K" first="Katrina" last="Sleeman">Katrina Sleeman</name></author><author><name sortKey="Johnson, Michael E" sort="Johnson, Michael E" uniqKey="Johnson M" first="Michael E" last="Johnson">Michael E. Johnson</name></author><author><name sortKey="Mesecar, Andrew D" sort="Mesecar, Andrew D" uniqKey="Mesecar A" first="Andrew D" last="Mesecar">Andrew D. Mesecar</name></author></analytic><series><title level="j">Bioorganic & medicinal chemistry letters</title><idno type="eISSN">1464-3405</idno><imprint><date when="2008" type="published">2008</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Animals</term><term>Antiviral Agents (chemical synthesis)</term><term>Antiviral Agents (chemistry)</term><term>Antiviral Agents (pharmacology)</term><term>Catalytic Domain</term><term>Chemistry, Pharmaceutical (methods)</term><term>Cysteine Endopeptidases (chemistry)</term><term>Drug Design</term><term>Esters</term><term>Humans</term><term>Inhibitory Concentration 50</term><term>Models, Chemical</term><term>Models, Molecular</term><term>Molecular Conformation</term><term>Protein Binding</term><term>SARS Virus (metabolism)</term><term>Viral Proteins (antagonists & inhibitors)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Animaux</term><term>Antiviraux ()</term><term>Antiviraux (pharmacologie)</term><term>Antiviraux (synthèse chimique)</term><term>Chimie pharmaceutique ()</term><term>Concentration inhibitrice 50</term><term>Conception de médicament</term><term>Conformation moléculaire</term><term>Cysteine endopeptidases ()</term><term>Domaine catalytique</term><term>Esters</term><term>Humains</term><term>Liaison aux protéines</term><term>Modèles chimiques</term><term>Modèles moléculaires</term><term>Protéines virales (antagonistes et inhibiteurs)</term><term>Virus du SRAS (métabolisme)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="antagonists & inhibitors" xml:lang="en"><term>Viral Proteins</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Antiviral Agents</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Antiviral Agents</term><term>Cysteine Endopeptidases</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Antiviral Agents</term></keywords><keywords scheme="MESH" qualifier="antagonistes et inhibiteurs" xml:lang="fr"><term>Protéines virales</term></keywords><keywords scheme="MESH" qualifier="metabolism" xml:lang="en"><term>SARS Virus</term></keywords><keywords scheme="MESH" qualifier="methods" xml:lang="en"><term>Chemistry, Pharmaceutical</term></keywords><keywords scheme="MESH" qualifier="métabolisme" xml:lang="fr"><term>Virus du SRAS</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Antiviraux</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Antiviraux</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Animals</term><term>Catalytic Domain</term><term>Drug Design</term><term>Esters</term><term>Humans</term><term>Inhibitory Concentration 50</term><term>Models, Chemical</term><term>Models, Molecular</term><term>Molecular Conformation</term><term>Protein Binding</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Animaux</term><term>Antiviraux</term><term>Chimie pharmaceutique</term><term>Concentration inhibitrice 50</term><term>Conception de médicament</term><term>Conformation moléculaire</term><term>Cysteine endopeptidases</term><term>Domaine catalytique</term><term>Esters</term><term>Humains</term><term>Liaison aux protéines</term><term>Modèles chimiques</term><term>Modèles moléculaires</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Design, synthesis and biological evaluation of a series of 5-chloropyridine ester-derived severe acute respiratory syndrome-coronavirus chymotrypsin-like protease inhibitors is described. Position of the carboxylate functionality is critical to potency. Inhibitor 10 with a 5-chloropyridinyl ester at position 4 of the indole ring is the most potent inhibitor with a SARS-CoV 3CLpro IC(50) value of 30 nM and an antiviral EC(50) value of 6.9 microM. Molecular docking studies have provided possible binding modes of these inhibitors.</div></front></TEI></pubmed></double></record>Pour manipuler ce document sous Unix (Dilib)
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