SrasV1, PascalFrancis, Corpus, bibRecord, 000241

Design, synthesis and antiviral efficacy of a series of potent chloropyridyl ester-derived SARS-CoV 3CLpro inhibitors

Identifieur interne : 000241 ( PascalFrancis/Corpus ); précédent : 000240; suivant : 000242

Design, synthesis and antiviral efficacy of a series of potent chloropyridyl ester-derived SARS-CoV 3CLpro inhibitors

Auteurs : Arun K. Ghosh ; GANGLI GONG ; Valerie Grum-Tokars ; Debbie C. Mulhearn ; Susan C. Baker ; Melissa Coughlin ; Bellur S. Prabhakar ; Katrina Sleeman ; Michael E. Johnson ; Andrew D. Mesecar

Source :

Bioorganic & medicinal chemistry letters : (Print) [ 0960-894X ] ; 2008.

RBID : Pascal:09-0033367

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 :
- Antiviral, Aromatic compound, Bicyclic compound, Chemical synthesis, Cysteine endopeptidases, Enzyme inhibitor, In vitro, Inhibitor enzyme complex, Modeling, Molecular model, Nitrogen heterocycle, Pyridine derivatives, Severe acute respiratory syndrome virus, Structure activity relation.

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.

Notice en format standard (ISO 2709)

Pour connaître la documentation sur le format Inist Standard.

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A11	`02`	`1`		`@1 GANGLI GONG`
A11	`03`	`1`		`@1 GRUM-TOKARS (Valerie)`
A11	`04`	`1`		`@1 MULHEARN (Debbie C.)`
A11	`05`	`1`		`@1 BAKER (Susan C.)`
A11	`06`	`1`		`@1 COUGHLIN (Melissa)`
A11	`07`	`1`		`@1 PRABHAKAR (Bellur S.)`
A11	`08`	`1`		`@1 SLEEMAN (Katrina)`
A11	`09`	`1`		`@1 JOHNSON (Michael E.)`
A11	`10`	`1`		`@1 MESECAR (Andrew D.)`
A14	`01`			`@1 Departments of Chemistry and Medicinal Chemistry. Purdue University, 560 Oval drive @2 West Lafayette, IN 47907 @3 USA @Z 1 aut. @Z 2 aut.`
A14	`02`			`@1 Center for Pharmaceutical Biotechnology, Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, 900 S @2 Ashland, IL 60607 @3 USA @Z 3 aut. @Z 4 aut. @Z 9 aut. @Z 10 aut.`
A14	`03`			`@1 Department of Microbiology and Immunology, Loyola University of Chicago, Stritch School of Medicine @2 Maywood, IL @3 USA @Z 5 aut. @Z 8 aut.`
A14	`04`			`@1 Department of Microbiology and Immunology, University of Illinois @2 Chicago, IL 60607 @3 USA @Z 6 aut. @Z 7 aut.`
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C03	`03`	`X`	`FRE`	`@0 Relation structure activité @5 03`
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C03	`07`	`X`	`ENG`	`@0 Nitrogen heterocycle @5 07`
C03	`07`	`X`	`SPA`	`@0 Heterociclo nitrógeno @5 07`
C03	`08`	`X`	`FRE`	`@0 Composé bicyclique @5 08`
C03	`08`	`X`	`ENG`	`@0 Bicyclic compound @5 08`
C03	`08`	`X`	`SPA`	`@0 Compuesto bicíclico @5 08`
C03	`09`	`X`	`FRE`	`@0 Composé aromatique @5 09`
C03	`09`	`X`	`ENG`	`@0 Aromatic compound @5 09`
C03	`09`	`X`	`SPA`	`@0 Compuesto aromático @5 09`
C03	`10`	`X`	`FRE`	`@0 Dérivé de la pyridine @5 11`
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C03	`11`	`X`	`FRE`	`@0 Modèle moléculaire @5 12`
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Format Inist (serveur)

NO :	PASCAL 09-0033367 INIST
ET :	Design, synthesis and antiviral efficacy of a series of potent chloropyridyl ester-derived SARS-CoV 3CLpro inhibitors
AU :	GHOSH (Arun K.); GANGLI GONG; GRUM-TOKARS (Valerie); MULHEARN (Debbie C.); BAKER (Susan C.); COUGHLIN (Melissa); PRABHAKAR (Bellur S.); SLEEMAN (Katrina); JOHNSON (Michael E.); MESECAR (Andrew D.)
AF :	Departments of Chemistry and Medicinal Chemistry. Purdue University, 560 Oval drive/West Lafayette, IN 47907/Etats-Unis (1 aut., 2 aut.); Center for Pharmaceutical Biotechnology, Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, 900 S/Ashland, IL 60607/Etats-Unis (3 aut., 4 aut., 9 aut., 10 aut.); Department of Microbiology and Immunology, Loyola University of Chicago, Stritch School of Medicine/Maywood, IL/Etats-Unis (5 aut., 8 aut.); Department of Microbiology and Immunology, University of Illinois/Chicago, IL 60607/Etats-Unis (6 aut., 7 aut.)
DT :	Publication en série; Niveau analytique
SO :	Bioorganic & medicinal chemistry letters : (Print); ISSN 0960-894X; Royaume-Uni; Da. 2008; Vol. 18; No. 20; Pp. 5684-5688; Bibl. 24 ref.
LA :	Anglais
EA :	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.
CC :	002B02S05
FD :	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
FG :	Peptidases; Hydrolases; Enzyme; Coronavirus; Coronaviridae; Nidovirales; Virus; Chlore Composé organique
ED :	Chemical synthesis; Antiviral; Structure activity relation; In vitro; Cysteine endopeptidases; Severe acute respiratory syndrome virus; Nitrogen heterocycle; Bicyclic compound; Aromatic compound; Pyridine derivatives; Molecular model; Inhibitor enzyme complex; Modeling; Enzyme inhibitor
EG :	Peptidases; Hydrolases; Enzyme; Coronavirus; Coronaviridae; Nidovirales; Virus; Chlorine Organic compounds
SD :	Síntesis química; Antiviral; Relación estructura actividad; In vitro; Cysteine endopeptidases; Severe acute respiratory syndrome virus; Heterociclo nitrógeno; Compuesto bicíclico; Compuesto aromático; Piridina derivado; Modelo molecular; Complejo enzima inhibidor; Modelización; Inhibidor enzima
LO :	INIST-22446.354000184446880790
ID :	09-0033367

Links to Exploration step

Pascal:09-0033367

Le document en format XML

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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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<sourceDesc><biblStruct><analytic><title xml:lang="en" level="a">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="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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<author><name sortKey="Baker, Susan C" sort="Baker, Susan C" uniqKey="Baker S" first="Susan C." last="Baker">Susan C. Baker</name>
<affiliation><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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<author><name sortKey="Coughlin, Melissa" sort="Coughlin, Melissa" uniqKey="Coughlin M" first="Melissa" last="Coughlin">Melissa Coughlin</name>
<affiliation><inist:fA14 i1="04"><s1>Department of Microbiology and Immunology, University of Illinois</s1>
<s2>Chicago, IL 60607</s2>
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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>
<affiliation><inist:fA14 i1="04"><s1>Department of Microbiology and Immunology, University of Illinois</s1>
<s2>Chicago, IL 60607</s2>
<s3>USA</s3>
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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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<s2>Maywood, IL</s2>
<s3>USA</s3>
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</author>
<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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<s2>Ashland, IL 60607</s2>
<s3>USA</s3>
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</author>
<author><name sortKey="Mesecar, Andrew D" sort="Mesecar, Andrew D" uniqKey="Mesecar A" first="Andrew D." last="Mesecar">Andrew D. Mesecar</name>
<affiliation><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>
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<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>
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<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>
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<term>Composé aromatique</term>
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<term>Modèle moléculaire</term>
<term>Complexe enzyme inhibiteur</term>
<term>Modélisation</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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<fA06><s2>20</s2>
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<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>
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<fA11 i1="01" i2="1"><s1>GHOSH (Arun K.)</s1>
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<fA11 i1="02" i2="1"><s1>GANGLI GONG</s1>
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<fA11 i1="03" i2="1"><s1>GRUM-TOKARS (Valerie)</s1>
</fA11>
<fA11 i1="04" i2="1"><s1>MULHEARN (Debbie C.)</s1>
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<fA11 i1="05" i2="1"><s1>BAKER (Susan C.)</s1>
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<fA11 i1="06" i2="1"><s1>COUGHLIN (Melissa)</s1>
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<fA11 i1="07" i2="1"><s1>PRABHAKAR (Bellur S.)</s1>
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<fA11 i1="08" i2="1"><s1>SLEEMAN (Katrina)</s1>
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<fA11 i1="09" i2="1"><s1>JOHNSON (Michael E.)</s1>
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<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>
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<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>
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</fA20>
<fA21><s1>2008</s1>
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<fA23 i1="01"><s0>ENG</s0>
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<fA43 i1="01"><s1>INIST</s1>
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<fA44><s0>0000</s0>
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</fA44>
<fA45><s0>24 ref.</s0>
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<fA47 i1="01" i2="1"><s0>09-0033367</s0>
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<fA60><s1>P</s1>
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<fA64 i1="01" i2="1"><s0>Bioorganic & medicinal chemistry letters : (Print)</s0>
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<fA66 i1="01"><s0>GBR</s0>
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<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. Molecular docking studies have provided possible binding modes of these inhibitors.</s0>
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<fC02 i1="01" i2="X"><s0>002B02S05</s0>
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<fC03 i1="01" i2="X" l="FRE"><s0>Synthèse chimique</s0>
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<s2>FE</s2>
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<fC03 i1="06" i2="X" l="FRE"><s0>Virus syndrome respiratoire aigu sévère</s0>
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<fC03 i1="06" i2="X" l="ENG"><s0>Severe acute respiratory syndrome virus</s0>
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<s5>08</s5>
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<s5>09</s5>
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<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>
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<s5>32</s5>
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<s5>33</s5>
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<s5>33</s5>
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<fC03 i1="14" i2="X" l="SPA"><s0>Inhibidor enzima</s0>
<s5>33</s5>
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<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>
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<fC07 i1="01" i2="X" l="FRE"><s0>Peptidases</s0>
<s2>FE</s2>
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<fC07 i1="04" i2="X" l="SPA"><s0>Coronavirus</s0>
<s2>NW</s2>
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<fC07 i1="05" i2="X" l="FRE"><s0>Coronaviridae</s0>
<s2>NW</s2>
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<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>
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<fC07 i1="06" i2="X" l="FRE"><s0>Nidovirales</s0>
<s2>NW</s2>
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<fC07 i1="06" i2="X" l="ENG"><s0>Nidovirales</s0>
<s2>NW</s2>
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<fC07 i1="06" i2="X" l="SPA"><s0>Nidovirales</s0>
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<fC07 i1="07" i2="X" l="FRE"><s0>Virus</s0>
<s2>NW</s2>
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<s2>NW</s2>
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<s2>NW</s2>
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<fC07 i1="08" i2="X" l="FRE"><s0>Chlore Composé organique</s0>
<s2>NC</s2>
<s2>FX</s2>
<s2>NA</s2>
<s5>10</s5>
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<fC07 i1="08" i2="X" l="ENG"><s0>Chlorine Organic compounds</s0>
<s2>NC</s2>
<s2>FX</s2>
<s2>NA</s2>
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<fC07 i1="08" i2="X" l="SPA"><s0>Cloro Compuesto orgánico</s0>
<s2>NC</s2>
<s2>FX</s2>
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<server><NO>PASCAL 09-0033367 INIST</NO>
<ET>Design, synthesis and antiviral efficacy of a series of potent chloropyridyl ester-derived SARS-CoV 3CLpro inhibitors</ET>
<AU>GHOSH (Arun K.); GANGLI GONG; GRUM-TOKARS (Valerie); MULHEARN (Debbie C.); BAKER (Susan C.); COUGHLIN (Melissa); PRABHAKAR (Bellur S.); SLEEMAN (Katrina); JOHNSON (Michael E.); MESECAR (Andrew D.)</AU>
<AF>Departments of Chemistry and Medicinal Chemistry. Purdue University, 560 Oval drive/West Lafayette, IN 47907/Etats-Unis (1 aut., 2 aut.); Center for Pharmaceutical Biotechnology, Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, 900 S/Ashland, IL 60607/Etats-Unis (3 aut., 4 aut., 9 aut., 10 aut.); Department of Microbiology and Immunology, Loyola University of Chicago, Stritch School of Medicine/Maywood, IL/Etats-Unis (5 aut., 8 aut.); Department of Microbiology and Immunology, University of Illinois/Chicago, IL 60607/Etats-Unis (6 aut., 7 aut.)</AF>
<DT>Publication en série; Niveau analytique</DT>
<SO>Bioorganic & medicinal chemistry letters : (Print); ISSN 0960-894X; Royaume-Uni; Da. 2008; Vol. 18; No. 20; Pp. 5684-5688; Bibl. 24 ref.</SO>
<LA>Anglais</LA>
<EA>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.</EA>
<CC>002B02S05</CC>
<FD>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</FD>
<FG>Peptidases; Hydrolases; Enzyme; Coronavirus; Coronaviridae; Nidovirales; Virus; Chlore Composé organique</FG>
<ED>Chemical synthesis; Antiviral; Structure activity relation; In vitro; Cysteine endopeptidases; Severe acute respiratory syndrome virus; Nitrogen heterocycle; Bicyclic compound; Aromatic compound; Pyridine derivatives; Molecular model; Inhibitor enzyme complex; Modeling; Enzyme inhibitor</ED>
<EG>Peptidases; Hydrolases; Enzyme; Coronavirus; Coronaviridae; Nidovirales; Virus; Chlorine Organic compounds</EG>
<SD>Síntesis química; Antiviral; Relación estructura actividad; In vitro; Cysteine endopeptidases; Severe acute respiratory syndrome virus; Heterociclo nitrógeno; Compuesto bicíclico; Compuesto aromático; Piridina derivado; Modelo molecular; Complejo enzima inhibidor; Modelización; Inhibidor enzima</SD>
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Design, synthesis and antiviral efficacy of a series of potent chloropyridyl ester-derived SARS-CoV 3CLpro inhibitors

Design, synthesis and antiviral efficacy of a series of potent chloropyridyl ester-derived SARS-CoV 3CLpro inhibitors

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