Design, synthesis and antiviral efficacy of a series of potent chloropyridyl ester-derived SARS-CoV 3CLpro inhibitors
Identifieur interne : 000747 ( PascalFrancis/Curation ); précédent : 000746; suivant : 000748Design, 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
- Pascal (Inist)
- 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 :
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.
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Ghosh</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Departments of Chemistry and Medicinal Chemistry. Purdue University, 560 Oval drive</s1><s2>West Lafayette, IN 47907</s2><s3>USA</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ></inist:fA14><country>États-Unis</country></affiliation></author><author><name sortKey="Gangli Gong" sort="Gangli Gong" uniqKey="Gangli Gong" last="Gangli Gong">GANGLI GONG</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Departments of Chemistry and Medicinal Chemistry. Purdue University, 560 Oval drive</s1><s2>West Lafayette, IN 47907</s2><s3>USA</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ></inist:fA14><country>États-Unis</country></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="1"><inist:fA14 i1="02"><s1>Center for Pharmaceutical Biotechnology, Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, 900 S</s1><s2>Ashland, IL 60607</s2><s3>USA</s3><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ></inist:fA14><country>États-Unis</country></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="1"><inist:fA14 i1="02"><s1>Center for Pharmaceutical Biotechnology, Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, 900 S</s1><s2>Ashland, IL 60607</s2><s3>USA</s3><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ></inist:fA14><country>États-Unis</country></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="1"><inist:fA14 i1="03"><s1>Department of Microbiology and Immunology, Loyola University of Chicago, Stritch School of Medicine</s1><s2>Maywood, IL</s2><s3>USA</s3><sZ>5 aut.</sZ><sZ>8 aut.</sZ></inist:fA14><country>États-Unis</country></affiliation></author><author><name sortKey="Coughlin, Melissa" sort="Coughlin, Melissa" uniqKey="Coughlin M" first="Melissa" last="Coughlin">Melissa Coughlin</name><affiliation wicri:level="1"><inist:fA14 i1="04"><s1>Department of Microbiology and Immunology, University of Illinois</s1><s2>Chicago, IL 60607</s2><s3>USA</s3><sZ>6 aut.</sZ><sZ>7 aut.</sZ></inist:fA14><country>États-Unis</country></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="1"><inist:fA14 i1="04"><s1>Department of Microbiology and Immunology, University of Illinois</s1><s2>Chicago, IL 60607</s2><s3>USA</s3><sZ>6 aut.</sZ><sZ>7 aut.</sZ></inist:fA14><country>États-Unis</country></affiliation></author><author><name sortKey="Sleeman, Katrina" sort="Sleeman, Katrina" uniqKey="Sleeman K" first="Katrina" last="Sleeman">Katrina Sleeman</name><affiliation wicri:level="1"><inist:fA14 i1="03"><s1>Department of Microbiology and Immunology, Loyola University of Chicago, Stritch School of Medicine</s1><s2>Maywood, IL</s2><s3>USA</s3><sZ>5 aut.</sZ><sZ>8 aut.</sZ></inist:fA14><country>États-Unis</country></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="1"><inist:fA14 i1="02"><s1>Center for Pharmaceutical Biotechnology, Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, 900 S</s1><s2>Ashland, IL 60607</s2><s3>USA</s3><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ></inist:fA14><country>États-Unis</country></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="1"><inist:fA14 i1="02"><s1>Center for Pharmaceutical Biotechnology, Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, 900 S</s1><s2>Ashland, IL 60607</s2><s3>USA</s3><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ></inist:fA14><country>États-Unis</country></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><idno type="ISSN">0960-894X</idno><imprint><date when="2008">2008</date></imprint></series></biblStruct></sourceDesc><seriesStmt><title level="j" type="main">Bioorganic & medicinal chemistry letters : (Print)</title><title level="j" type="abbreviated">Bioorg. med. chem. lett. : (Print)</title><idno type="ISSN">0960-894X</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Antiviral</term><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><term>Indole-4-carboxylique acide ester 5-chloro-3-pyridyle</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<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><inist><standard h6="B"><pA><fA01 i1="01" i2="1"><s0>0960-894X</s0></fA01><fA03 i2="1"><s0>Bioorg. med. chem. lett. : (Print)</s0></fA03><fA05><s2>18</s2></fA05><fA06><s2>20</s2></fA06><fA08 i1="01" i2="1" l="ENG"><s1>Design, synthesis and antiviral efficacy of a series of potent chloropyridyl ester-derived SARS-CoV 3CLpro inhibitors</s1></fA08><fA11 i1="01" i2="1"><s1>GHOSH (Arun K.)</s1></fA11><fA11 i1="02" i2="1"><s1>GANGLI GONG</s1></fA11><fA11 i1="03" i2="1"><s1>GRUM-TOKARS (Valerie)</s1></fA11><fA11 i1="04" i2="1"><s1>MULHEARN (Debbie C.)</s1></fA11><fA11 i1="05" i2="1"><s1>BAKER (Susan C.)</s1></fA11><fA11 i1="06" i2="1"><s1>COUGHLIN (Melissa)</s1></fA11><fA11 i1="07" i2="1"><s1>PRABHAKAR (Bellur S.)</s1></fA11><fA11 i1="08" i2="1"><s1>SLEEMAN (Katrina)</s1></fA11><fA11 i1="09" i2="1"><s1>JOHNSON (Michael E.)</s1></fA11><fA11 i1="10" i2="1"><s1>MESECAR (Andrew D.)</s1></fA11><fA14 i1="01"><s1>Departments of Chemistry and Medicinal Chemistry. Purdue University, 560 Oval drive</s1><s2>West Lafayette, IN 47907</s2><s3>USA</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ></fA14><fA14 i1="02"><s1>Center for Pharmaceutical Biotechnology, Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, 900 S</s1><s2>Ashland, IL 60607</s2><s3>USA</s3><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ></fA14><fA14 i1="03"><s1>Department of Microbiology and Immunology, Loyola University of Chicago, Stritch School of Medicine</s1><s2>Maywood, IL</s2><s3>USA</s3><sZ>5 aut.</sZ><sZ>8 aut.</sZ></fA14><fA14 i1="04"><s1>Department of Microbiology and Immunology, University of Illinois</s1><s2>Chicago, IL 60607</s2><s3>USA</s3><sZ>6 aut.</sZ><sZ>7 aut.</sZ></fA14><fA20><s1>5684-5688</s1></fA20><fA21><s1>2008</s1></fA21><fA23 i1="01"><s0>ENG</s0></fA23><fA43 i1="01"><s1>INIST</s1><s2>22446</s2><s5>354000184446880790</s5></fA43><fA44><s0>0000</s0><s1>© 2009 INIST-CNRS. All rights reserved.</s1></fA44><fA45><s0>24 ref.</s0></fA45><fA47 i1="01" i2="1"><s0>09-0033367</s0></fA47><fA60><s1>P</s1></fA60><fA61><s0>A</s0></fA61><fA64 i1="01" i2="1"><s0>Bioorganic & medicinal chemistry letters : (Print)</s0></fA64><fA66 i1="01"><s0>GBR</s0></fA66><fC01 i1="01" l="ENG"><s0>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. 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vitro</s0><s5>04</s5></fC03><fC03 i1="05" i2="X" l="FRE"><s0>Cysteine endopeptidases</s0><s2>FE</s2><s5>05</s5></fC03><fC03 i1="05" i2="X" l="ENG"><s0>Cysteine endopeptidases</s0><s2>FE</s2><s5>05</s5></fC03><fC03 i1="05" i2="X" l="SPA"><s0>Cysteine endopeptidases</s0><s2>FE</s2><s5>05</s5></fC03><fC03 i1="06" i2="X" l="FRE"><s0>Virus syndrome respiratoire aigu sévère</s0><s2>NW</s2><s5>06</s5></fC03><fC03 i1="06" i2="X" l="ENG"><s0>Severe acute respiratory syndrome virus</s0><s2>NW</s2><s5>06</s5></fC03><fC03 i1="06" i2="X" l="SPA"><s0>Severe acute respiratory syndrome virus</s0><s2>NW</s2><s5>06</s5></fC03><fC03 i1="07" i2="X" l="FRE"><s0>Hétérocycle azote</s0><s5>07</s5></fC03><fC03 i1="07" i2="X" l="ENG"><s0>Nitrogen heterocycle</s0><s5>07</s5></fC03><fC03 i1="07" i2="X" l="SPA"><s0>Heterociclo nitrógeno</s0><s5>07</s5></fC03><fC03 i1="08" i2="X" l="FRE"><s0>Composé bicyclique</s0><s5>08</s5></fC03><fC03 i1="08" i2="X" l="ENG"><s0>Bicyclic compound</s0><s5>08</s5></fC03><fC03 i1="08" i2="X" l="SPA"><s0>Compuesto bicíclico</s0><s5>08</s5></fC03><fC03 i1="09" i2="X" l="FRE"><s0>Composé aromatique</s0><s5>09</s5></fC03><fC03 i1="09" i2="X" l="ENG"><s0>Aromatic compound</s0><s5>09</s5></fC03><fC03 i1="09" i2="X" l="SPA"><s0>Compuesto aromático</s0><s5>09</s5></fC03><fC03 i1="10" i2="X" l="FRE"><s0>Dérivé de la pyridine</s0><s5>11</s5></fC03><fC03 i1="10" i2="X" l="ENG"><s0>Pyridine derivatives</s0><s5>11</s5></fC03><fC03 i1="10" i2="X" l="SPA"><s0>Piridina derivado</s0><s5>11</s5></fC03><fC03 i1="11" i2="X" l="FRE"><s0>Modèle moléculaire</s0><s5>12</s5></fC03><fC03 i1="11" i2="X" l="ENG"><s0>Molecular model</s0><s5>12</s5></fC03><fC03 i1="11" i2="X" l="SPA"><s0>Modelo molecular</s0><s5>12</s5></fC03><fC03 i1="12" i2="X" l="FRE"><s0>Complexe enzyme inhibiteur</s0><s5>13</s5></fC03><fC03 i1="12" i2="X" l="ENG"><s0>Inhibitor enzyme complex</s0><s5>13</s5></fC03><fC03 i1="12" i2="X" l="SPA"><s0>Complejo enzima inhibidor</s0><s5>13</s5></fC03><fC03 i1="13" i2="X" l="FRE"><s0>Modélisation</s0><s5>32</s5></fC03><fC03 i1="13" i2="X" l="ENG"><s0>Modeling</s0><s5>32</s5></fC03><fC03 i1="13" i2="X" l="SPA"><s0>Modelización</s0><s5>32</s5></fC03><fC03 i1="14" i2="X" l="FRE"><s0>Inhibiteur enzyme</s0><s5>33</s5></fC03><fC03 i1="14" i2="X" l="ENG"><s0>Enzyme inhibitor</s0><s5>33</s5></fC03><fC03 i1="14" i2="X" l="SPA"><s0>Inhibidor enzima</s0><s5>33</s5></fC03><fC03 i1="15" i2="X" l="FRE"><s0>Indole-4-carboxylique acide ester 5-chloro-3-pyridyle</s0><s2>NK</s2><s2>FR</s2><s4>INC</s4><s5>76</s5></fC03><fC07 i1="01" i2="X" l="FRE"><s0>Peptidases</s0><s2>FE</s2></fC07><fC07 i1="01" i2="X" l="ENG"><s0>Peptidases</s0><s2>FE</s2></fC07><fC07 i1="01" i2="X" l="SPA"><s0>Peptidases</s0><s2>FE</s2></fC07><fC07 i1="02" i2="X" l="FRE"><s0>Hydrolases</s0><s2>FE</s2></fC07><fC07 i1="02" i2="X" l="ENG"><s0>Hydrolases</s0><s2>FE</s2></fC07><fC07 i1="02" i2="X" l="SPA"><s0>Hydrolases</s0><s2>FE</s2></fC07><fC07 i1="03" i2="X" l="FRE"><s0>Enzyme</s0><s2>FE</s2></fC07><fC07 i1="03" i2="X" l="ENG"><s0>Enzyme</s0><s2>FE</s2></fC07><fC07 i1="03" i2="X" l="SPA"><s0>Enzima</s0><s2>FE</s2></fC07><fC07 i1="04" i2="X" l="FRE"><s0>Coronavirus</s0><s2>NW</s2></fC07><fC07 i1="04" i2="X" l="ENG"><s0>Coronavirus</s0><s2>NW</s2></fC07><fC07 i1="04" i2="X" l="SPA"><s0>Coronavirus</s0><s2>NW</s2></fC07><fC07 i1="05" i2="X" l="FRE"><s0>Coronaviridae</s0><s2>NW</s2></fC07><fC07 i1="05" i2="X" l="ENG"><s0>Coronaviridae</s0><s2>NW</s2></fC07><fC07 i1="05" i2="X" l="SPA"><s0>Coronaviridae</s0><s2>NW</s2></fC07><fC07 i1="06" i2="X" l="FRE"><s0>Nidovirales</s0><s2>NW</s2></fC07><fC07 i1="06" i2="X" l="ENG"><s0>Nidovirales</s0><s2>NW</s2></fC07><fC07 i1="06" i2="X" l="SPA"><s0>Nidovirales</s0><s2>NW</s2></fC07><fC07 i1="07" i2="X" l="FRE"><s0>Virus</s0><s2>NW</s2></fC07><fC07 i1="07" i2="X" l="ENG"><s0>Virus</s0><s2>NW</s2></fC07><fC07 i1="07" i2="X" l="SPA"><s0>Virus</s0><s2>NW</s2></fC07><fC07 i1="08" i2="X" l="FRE"><s0>Chlore Composé organique</s0><s2>NC</s2><s2>FX</s2><s2>NA</s2><s5>10</s5></fC07><fC07 i1="08" i2="X" l="ENG"><s0>Chlorine Organic compounds</s0><s2>NC</s2><s2>FX</s2><s2>NA</s2><s5>10</s5></fC07><fC07 i1="08" i2="X" l="SPA"><s0>Cloro Compuesto orgánico</s0><s2>NC</s2><s2>FX</s2><s2>NA</s2><s5>10</s5></fC07><fN21><s1>022</s1></fN21></pA></standard></inist></record>Pour manipuler ce document sous Unix (Dilib)
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|wiki= Sante
|area= SrasV1
|flux= PascalFrancis
|étape= Curation
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|texte= Design, synthesis and antiviral efficacy of a series of potent chloropyridyl ester-derived SARS-CoV 3CLpro inhibitors
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