Design, synthesis and antiviral efficacy of a series of potent chloropyridyl ester-derived SARS-CoV 3CLpro inhibitors
Identifieur interne : 000834 ( Pmc/Curation ); précédent : 000833; suivant : 000835Design, 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.
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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Ghosh</name><affiliation wicri:level="1"><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></affiliation></author><author><name sortKey="Gong, Gangli" sort="Gong, Gangli" uniqKey="Gong G" first="Gangli" last="Gong">Gangli Gong</name><affiliation wicri:level="1"><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></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"><nlm:aff id="aff2">Center for Pharmaceutical Biotechnology, Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, 900 S. 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Johnson</name><affiliation wicri:level="1"><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></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"><nlm:aff id="aff2">Center for Pharmaceutical Biotechnology, Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, 900 S. 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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></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"><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. 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Johnson</name><affiliation wicri:level="1"><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></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"><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. 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<front><journal-meta><journal-id journal-id-type="nlm-ta">Bioorg Med Chem Lett</journal-id><journal-id journal-id-type="iso-abbrev">Bioorg. Med. Chem. Lett</journal-id><journal-title-group><journal-title>Bioorganic & Medicinal Chemistry Letters</journal-title></journal-title-group><issn pub-type="ppub">0960-894X</issn><issn pub-type="epub">1464-3405</issn><publisher><publisher-name>Elsevier Ltd.</publisher-name></publisher></journal-meta><article-meta><article-id pub-id-type="pmid">18796354</article-id><article-id pub-id-type="pmc">2745596</article-id><article-id pub-id-type="publisher-id">S0960-894X(08)00986-4</article-id><article-id pub-id-type="doi">10.1016/j.bmcl.2008.08.082</article-id><article-categories><subj-group subj-group-type="heading"><subject>Article</subject></subj-group></article-categories><title-group><article-title>Design, synthesis and antiviral efficacy of a series of potent chloropyridyl ester-derived SARS-CoV 3CLpro inhibitors</article-title></title-group><contrib-group><contrib contrib-type="author"><name><surname>Ghosh</surname><given-names>Arun K.</given-names></name><email>akghosh@purdue.edu</email><xref rid="aff1" ref-type="aff">a</xref><xref rid="cor1" ref-type="corresp">⁎</xref></contrib><contrib contrib-type="author"><name><surname>Gong</surname><given-names>Gangli</given-names></name><xref rid="aff1" ref-type="aff">a</xref></contrib><contrib contrib-type="author"><name><surname>Grum-Tokars</surname><given-names>Valerie</given-names></name><xref rid="aff2" ref-type="aff">b</xref></contrib><contrib contrib-type="author"><name><surname>Mulhearn</surname><given-names>Debbie C.</given-names></name><xref rid="aff2" ref-type="aff">b</xref></contrib><contrib contrib-type="author"><name><surname>Baker</surname><given-names>Susan C.</given-names></name><xref rid="aff3" ref-type="aff">c</xref></contrib><contrib contrib-type="author"><name><surname>Coughlin</surname><given-names>Melissa</given-names></name><xref rid="aff4" ref-type="aff">d</xref></contrib><contrib contrib-type="author"><name><surname>Prabhakar</surname><given-names>Bellur S.</given-names></name><xref rid="aff4" ref-type="aff">d</xref></contrib><contrib contrib-type="author"><name><surname>Sleeman</surname><given-names>Katrina</given-names></name><xref rid="aff3" ref-type="aff">c</xref></contrib><contrib contrib-type="author"><name><surname>Johnson</surname><given-names>Michael E.</given-names></name><xref rid="aff2" ref-type="aff">b</xref></contrib><contrib contrib-type="author"><name><surname>Mesecar</surname><given-names>Andrew D.</given-names></name><xref rid="aff2" ref-type="aff">b</xref></contrib></contrib-group><aff id="aff1"><label>a</label>Departments of Chemistry and Medicinal Chemistry, Purdue University, 560 Oval drive, West Lafayette, IN 47907, USA</aff><aff id="aff2"><label>b</label>Center for Pharmaceutical Biotechnology, Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, 900 S. Ashland, IL 60607, USA</aff><aff id="aff3"><label>c</label>Department of Microbiology and Immunology, Loyola University of Chicago, Stritch School of Medicine, Maywood, IL, USA</aff><aff id="aff4"><label>d</label>Department of Microbiology and Immunology, University of Illinois at Chicago, IL 60607, USA</aff><author-notes><corresp id="cor1"><label>⁎</label>Corresponding author. Tel.: +1 765 494 5323; fax: +1 765 496 1612. <email>akghosh@purdue.edu</email></corresp></author-notes><pub-date pub-type="pmc-release"><day>28</day><month>8</month><year>2008</year></pub-date><pmc-comment> PMC Release delay is 0 months and 0 days and was based on .</pmc-comment>
<pub-date pub-type="ppub"><day>15</day><month>10</month><year>2008</year></pub-date><pub-date pub-type="epub"><day>28</day><month>8</month><year>2008</year></pub-date><volume>18</volume><issue>20</issue><fpage>5684</fpage><lpage>5688</lpage><history><date date-type="received"><day>15</day><month>7</month><year>2008</year></date><date date-type="rev-recd"><day>12</day><month>8</month><year>2008</year></date><date date-type="accepted"><day>15</day><month>8</month><year>2008</year></date></history><permissions><copyright-statement>Copyright © 2008 Elsevier Ltd. All rights reserved.</copyright-statement><copyright-year>2008</copyright-year><copyright-holder>Elsevier Ltd</copyright-holder><license><license-p>Since January 2020 Elsevier has created a COVID-19 resource centre with free information in English and Mandarin on the novel coronavirus COVID-19. The COVID-19 resource centre is hosted on Elsevier Connect, the company's public news and information website. Elsevier hereby grants permission to make all its COVID-19-related research that is available on the COVID-19 resource centre - including this research content - immediately available in PubMed Central and other publicly funded repositories, such as the WHO COVID database with rights for unrestricted research re-use and analyses in any form or by any means with acknowledgement of the original source. These permissions are granted for free by Elsevier for as long as the COVID-19 resource centre remains active.</license-p></license></permissions><abstract abstract-type="graphical"><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></abstract><abstract><p>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 <bold>10</bold> 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.</p></abstract><kwd-group><title>Keywords</title><kwd>Synthesis</kwd><kwd>SARS 3CLpro</kwd><kwd>Ester</kwd><kwd>Antiviral</kwd><kwd>Inhibitor</kwd></kwd-group></article-meta></front></pmc></record>Pour manipuler ce document sous Unix (Dilib)
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