Design, synthesis and antiviral efficacy of a series of potent chloropyridyl ester-derived SARS-CoV 3CLpro inhibitors
Identifieur interne : 003511 ( Main/Curation ); précédent : 003510; suivant : 003512Design, 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 : (Print) [ 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.
- Pascal (Inist)
- 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, Synthèse chimique, Antiviral, Relation structure activité, In vitro, Cysteine endopeptidases, Virus syndrome respiratoire aigu sévère, Hétérocycle azote, Composé bicyclique, Composé aromatique, Dérivé de la pyridine, Modèle moléculaire, Complexe enzyme inhibiteur, Modélisation, Inhibiteur enzyme, Indole-4-carboxylique acide ester 5-chloro-3-pyridyle.
English descriptors
- KwdEn :
- Animals, Antiviral, Antiviral Agents (chemical synthesis), Antiviral Agents (chemistry), Antiviral Agents (pharmacology), Aromatic compound, Bicyclic compound, Catalytic Domain, Chemical synthesis, Chemistry, Pharmaceutical (methods), Cysteine Endopeptidases (chemistry), Cysteine endopeptidases, Drug Design, Enzyme inhibitor, Esters, Humans, In vitro, Inhibitor enzyme complex, Inhibitory Concentration 50, Modeling, Models, Chemical, Models, Molecular, Molecular Conformation, Molecular model, Nitrogen heterocycle, Protein Binding, Pyridine derivatives, SARS Virus (metabolism), Severe acute respiratory syndrome virus, Structure activity relation, 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 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 IC50 value of 30 nM and an antiviral EC50 value of 6.9 μM. Molecular docking studies have provided possible binding modes of these inhibitors.
Url:
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Pascal:09-0033367Le document en format XML
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<author><name sortKey="Coughlin, Melissa" sort="Coughlin, Melissa" uniqKey="Coughlin M" first="Melissa" last="Coughlin">Melissa Coughlin</name>
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<author><name sortKey="Prabhakar, Bellur S" sort="Prabhakar, Bellur S" uniqKey="Prabhakar B" first="Bellur S." last="Prabhakar">Bellur S. Prabhakar</name>
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<author><name sortKey="Sleeman, Katrina" sort="Sleeman, Katrina" uniqKey="Sleeman K" first="Katrina" last="Sleeman">Katrina Sleeman</name>
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<author><name sortKey="Johnson, Michael E" sort="Johnson, Michael E" uniqKey="Johnson M" first="Michael E." last="Johnson">Michael E. Johnson</name>
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<author><name sortKey="Mesecar, Andrew D" sort="Mesecar, Andrew D" uniqKey="Mesecar A" first="Andrew D." last="Mesecar">Andrew D. Mesecar</name>
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</placeName>
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<profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Animals</term>
<term>Antiviral</term>
<term>Antiviral Agents (chemical synthesis)</term>
<term>Antiviral Agents (chemistry)</term>
<term>Antiviral Agents (pharmacology)</term>
<term>Aromatic compound</term>
<term>Bicyclic compound</term>
<term>Catalytic Domain</term>
<term>Chemical synthesis</term>
<term>Chemistry, Pharmaceutical (methods)</term>
<term>Cysteine Endopeptidases (chemistry)</term>
<term>Cysteine endopeptidases</term>
<term>Drug Design</term>
<term>Enzyme inhibitor</term>
<term>Esters</term>
<term>Humans</term>
<term>In vitro</term>
<term>Inhibitor enzyme complex</term>
<term>Inhibitory Concentration 50</term>
<term>Modeling</term>
<term>Models, Chemical</term>
<term>Models, Molecular</term>
<term>Molecular Conformation</term>
<term>Molecular model</term>
<term>Nitrogen heterocycle</term>
<term>Protein Binding</term>
<term>Pyridine derivatives</term>
<term>SARS Virus (metabolism)</term>
<term>Severe acute respiratory syndrome virus</term>
<term>Structure activity relation</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>
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</keywords>
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</keywords>
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<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="Pascal" 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>
<term>Synthèse chimique</term>
<term>Antiviral</term>
<term>Relation structure activité</term>
<term>In vitro</term>
<term>Cysteine endopeptidases</term>
<term>Virus syndrome respiratoire aigu sévère</term>
<term>Hétérocycle azote</term>
<term>Composé bicyclique</term>
<term>Composé aromatique</term>
<term>Dérivé de la pyridine</term>
<term>Modèle moléculaire</term>
<term>Complexe enzyme inhibiteur</term>
<term>Modélisation</term>
<term>Inhibiteur enzyme</term>
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<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<sub>50</sub>
value of 30 nM and an antiviral EC<sub>50</sub>
value of 6.9 μM. Molecular docking studies have provided possible binding modes of these inhibitors.</div>
</front>
</TEI>
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<orgName type="university">Université de Chicago</orgName>
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<author><name sortKey="Mesecar, Andrew D" sort="Mesecar, Andrew D" uniqKey="Mesecar A" first="Andrew D." last="Mesecar">Andrew D. Mesecar</name>
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<settlement type="city">Chicago</settlement>
</placeName>
<orgName type="university">Université de l'Illinois à Chicago</orgName>
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</affiliation>
</author>
<author><name sortKey="Gangli Gong" sort="Gangli Gong" uniqKey="Gangli Gong" last="Gangli Gong">GANGLI GONG</name>
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<author><name sortKey="Grum Tokars, Valerie" sort="Grum Tokars, Valerie" uniqKey="Grum Tokars V" first="Valerie" last="Grum-Tokars">Valerie Grum-Tokars</name>
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<author><name sortKey="Mulhearn, Debbie C" sort="Mulhearn, Debbie C" uniqKey="Mulhearn D" first="Debbie C." last="Mulhearn">Debbie C. Mulhearn</name>
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<settlement type="city">Chicago</settlement>
</placeName>
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</affiliation>
</author>
<author><name sortKey="Coughlin, Melissa" sort="Coughlin, Melissa" uniqKey="Coughlin M" first="Melissa" last="Coughlin">Melissa Coughlin</name>
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</placeName>
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<author><name sortKey="Prabhakar, Bellur S" sort="Prabhakar, Bellur S" uniqKey="Prabhakar B" first="Bellur S." last="Prabhakar">Bellur S. Prabhakar</name>
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<s2>Chicago, IL 60607</s2>
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<sZ>7 aut.</sZ>
</inist:fA14>
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<placeName><region type="state">Illinois</region>
</placeName>
</affiliation>
</author>
<author><name sortKey="Sleeman, Katrina" sort="Sleeman, Katrina" uniqKey="Sleeman K" first="Katrina" last="Sleeman">Katrina Sleeman</name>
<affiliation wicri:level="4"><inist:fA14 i1="03"><s1>Department of Microbiology and Immunology, Loyola University of Chicago, Stritch School of Medicine</s1>
<s2>Maywood, IL</s2>
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<sZ>5 aut.</sZ>
<sZ>8 aut.</sZ>
</inist:fA14>
<country>États-Unis</country>
<placeName><region type="state">Illinois</region>
<settlement type="city">Chicago</settlement>
</placeName>
<orgName type="university">Université de Chicago</orgName>
</affiliation>
</author>
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</placeName>
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<author><name sortKey="Mesecar, Andrew D" sort="Mesecar, Andrew D" uniqKey="Mesecar A" first="Andrew D." last="Mesecar">Andrew D. Mesecar</name>
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<s2>Ashland, IL 60607</s2>
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<sZ>4 aut.</sZ>
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<sZ>10 aut.</sZ>
</inist:fA14>
<country>États-Unis</country>
<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" type="main">Bioorganic & medicinal chemistry letters : (Print)</title>
<title level="j" type="abbreviated">Bioorg. med. chem. lett. : (Print)</title>
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</seriesStmt>
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<term>Aromatic compound</term>
<term>Bicyclic compound</term>
<term>Chemical synthesis</term>
<term>Cysteine endopeptidases</term>
<term>Enzyme inhibitor</term>
<term>In vitro</term>
<term>Inhibitor enzyme complex</term>
<term>Modeling</term>
<term>Molecular model</term>
<term>Nitrogen heterocycle</term>
<term>Pyridine derivatives</term>
<term>Severe acute respiratory syndrome virus</term>
<term>Structure activity relation</term>
</keywords>
<keywords scheme="Pascal" xml:lang="fr"><term>Synthèse chimique</term>
<term>Antiviral</term>
<term>Relation structure activité</term>
<term>In vitro</term>
<term>Cysteine endopeptidases</term>
<term>Virus syndrome respiratoire aigu sévère</term>
<term>Hétérocycle azote</term>
<term>Composé bicyclique</term>
<term>Composé aromatique</term>
<term>Dérivé de la pyridine</term>
<term>Modèle moléculaire</term>
<term>Complexe enzyme inhibiteur</term>
<term>Modélisation</term>
<term>Inhibiteur enzyme</term>
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<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<sub>50</sub>
value of 30 nM and an antiviral EC<sub>50</sub>
value of 6.9 μM. Molecular docking studies have provided possible binding modes of these inhibitors.</div>
</front>
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<PMC><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Design, synthesis and antiviral efficacy of a series of potent chloropyridyl ester-derived SARS-CoV 3CLpro inhibitors</title>
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<author><name sortKey="Mesecar, Andrew D" sort="Mesecar, Andrew D" uniqKey="Mesecar A" first="Andrew D." last="Mesecar">Andrew D. Mesecar</name>
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<country xml:lang="fr">États-Unis</country>
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<author><name sortKey="Ghosh, Arun K" sort="Ghosh, Arun K" uniqKey="Ghosh A" first="Arun K." last="Ghosh">Arun K. Ghosh</name>
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<author><name sortKey="Gong, Gangli" sort="Gong, Gangli" uniqKey="Gong G" first="Gangli" last="Gong">Gangli Gong</name>
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<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>
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</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>
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<country xml:lang="fr">États-Unis</country>
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</affiliation>
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<author><name sortKey="Baker, Susan C" sort="Baker, Susan C" uniqKey="Baker S" first="Susan C." last="Baker">Susan C. Baker</name>
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</affiliation>
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<author><name sortKey="Coughlin, Melissa" sort="Coughlin, Melissa" uniqKey="Coughlin M" first="Melissa" last="Coughlin">Melissa Coughlin</name>
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<country xml:lang="fr">États-Unis</country>
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<placeName><region type="state">Illinois</region>
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</affiliation>
</author>
<author><name sortKey="Prabhakar, Bellur S" sort="Prabhakar, Bellur S" uniqKey="Prabhakar B" first="Bellur S." last="Prabhakar">Bellur S. Prabhakar</name>
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<country xml:lang="fr">États-Unis</country>
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<placeName><region type="state">Illinois</region>
<settlement type="city">Chicago</settlement>
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<author><name sortKey="Sleeman, Katrina" sort="Sleeman, Katrina" uniqKey="Sleeman K" first="Katrina" last="Sleeman">Katrina Sleeman</name>
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<country xml:lang="fr">États-Unis</country>
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<placeName><region type="state">Illinois</region>
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<author><name sortKey="Johnson, Michael E" sort="Johnson, Michael E" uniqKey="Johnson M" first="Michael E." last="Johnson">Michael E. Johnson</name>
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<country xml:lang="fr">États-Unis</country>
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<placeName><region type="state">Illinois</region>
<settlement type="city">Chicago</settlement>
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</placeName>
<orgName type="university">Université de l'Illinois à Chicago</orgName>
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</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>
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<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>
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<keywords scheme="MESH" qualifier="methods" xml:lang="en"><term>Chemistry, Pharmaceutical</term>
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<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>
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<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>
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<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>
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