New developments for the design, synthesis and biological evaluation of potent SARS-CoV 3CL(pro) inhibitors.
Identifieur interne : 001930 ( PubMed/Corpus ); précédent : 001929; suivant : 001931New developments for the design, synthesis and biological evaluation of potent SARS-CoV 3CL(pro) inhibitors.
Auteurs : Thomas Regnier ; Diganta Sarma ; Koushi Hidaka ; Usman Bacha ; Ernesto Freire ; Yoshio Hayashi ; Yoshiaki KisoSource :
- Bioorganic & medicinal chemistry letters [ 1464-3405 ] ; 2009.
English descriptors
- KwdEn :
- Amino Acid Sequence, Antiviral Agents (chemical synthesis), Antiviral Agents (chemistry), Antiviral Agents (pharmacology), Benzothiazoles (chemical synthesis), Benzothiazoles (chemistry), Benzothiazoles (pharmacology), Chymases (antagonists & inhibitors), Chymases (metabolism), Computer Simulation, Cysteine Endopeptidases (metabolism), Drug Design, Ketones (chemical synthesis), Ketones (chemistry), Peptides (chemical synthesis), Peptides (chemistry), Peptides (pharmacology), Protease Inhibitors (chemical synthesis), Protease Inhibitors (chemistry), Protease Inhibitors (pharmacology), Pyrrolidinones (chemical synthesis), Pyrrolidinones (chemistry), Pyrrolidinones (pharmacology), SARS Virus, Structure-Activity Relationship, Thiazoles (chemical synthesis), Thiazoles (chemistry), Thiazoles (pharmacology), Viral Proteins (antagonists & inhibitors), Viral Proteins (metabolism).
- MESH :
- chemical , antagonists & inhibitors : Chymases, Viral Proteins.
- chemical , chemical synthesis : Antiviral Agents, Benzothiazoles, Ketones, Peptides, Protease Inhibitors, Pyrrolidinones, Thiazoles.
- chemical , chemistry : Antiviral Agents, Benzothiazoles, Ketones, Peptides, Protease Inhibitors, Pyrrolidinones, Thiazoles.
- chemical , metabolism : Chymases, Cysteine Endopeptidases, Viral Proteins.
- chemical , pharmacology : Antiviral Agents, Benzothiazoles, Peptides, Protease Inhibitors, Pyrrolidinones, Thiazoles.
- Amino Acid Sequence, Computer Simulation, Drug Design, SARS Virus, Structure-Activity Relationship.
Abstract
A series of trifluoromethyl, benzothiazolyl or thiazolyl ketone-containing peptidic compounds as SARS-CoV 3CL protease inhibitors were developed and their potency was evaluated by in vitro protease inhibitory assays. Three candidates had encouraging results for the development of new anti-SARS compounds.
DOI: 10.1016/j.bmcl.2009.03.118
PubMed: 19362479
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pubmed:19362479Le document en format XML
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first="Ernesto" last="Freire">Ernesto Freire</name></author><author><name sortKey="Hayashi, Yoshio" sort="Hayashi, Yoshio" uniqKey="Hayashi Y" first="Yoshio" last="Hayashi">Yoshio Hayashi</name></author><author><name sortKey="Kiso, Yoshiaki" sort="Kiso, Yoshiaki" uniqKey="Kiso Y" first="Yoshiaki" last="Kiso">Yoshiaki Kiso</name></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2009">2009</date><idno type="RBID">pubmed:19362479</idno><idno type="pmid">19362479</idno><idno type="doi">10.1016/j.bmcl.2009.03.118</idno><idno type="wicri:Area/PubMed/Corpus">001930</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">001930</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">New developments for the design, synthesis and biological evaluation of potent SARS-CoV 3CL(pro) inhibitors.</title><author><name sortKey="Regnier, Thomas" sort="Regnier, Thomas" uniqKey="Regnier T" first="Thomas" last="Regnier">Thomas Regnier</name><affiliation><nlm:affiliation>Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, Kyoto Pharmaceutical University, Japan.</nlm:affiliation></affiliation></author><author><name sortKey="Sarma, Diganta" sort="Sarma, Diganta" uniqKey="Sarma D" first="Diganta" last="Sarma">Diganta Sarma</name></author><author><name sortKey="Hidaka, Koushi" sort="Hidaka, Koushi" uniqKey="Hidaka K" first="Koushi" last="Hidaka">Koushi Hidaka</name></author><author><name sortKey="Bacha, Usman" sort="Bacha, Usman" uniqKey="Bacha U" first="Usman" last="Bacha">Usman Bacha</name></author><author><name sortKey="Freire, Ernesto" sort="Freire, Ernesto" uniqKey="Freire E" first="Ernesto" last="Freire">Ernesto Freire</name></author><author><name sortKey="Hayashi, Yoshio" sort="Hayashi, Yoshio" uniqKey="Hayashi Y" first="Yoshio" last="Hayashi">Yoshio Hayashi</name></author><author><name sortKey="Kiso, Yoshiaki" sort="Kiso, Yoshiaki" uniqKey="Kiso Y" first="Yoshiaki" last="Kiso">Yoshiaki Kiso</name></author></analytic><series><title level="j">Bioorganic & medicinal chemistry letters</title><idno type="eISSN">1464-3405</idno><imprint><date when="2009" type="published">2009</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Amino Acid Sequence</term><term>Antiviral Agents (chemical synthesis)</term><term>Antiviral Agents (chemistry)</term><term>Antiviral Agents (pharmacology)</term><term>Benzothiazoles (chemical synthesis)</term><term>Benzothiazoles (chemistry)</term><term>Benzothiazoles (pharmacology)</term><term>Chymases (antagonists & inhibitors)</term><term>Chymases (metabolism)</term><term>Computer Simulation</term><term>Cysteine Endopeptidases (metabolism)</term><term>Drug Design</term><term>Ketones (chemical synthesis)</term><term>Ketones (chemistry)</term><term>Peptides (chemical synthesis)</term><term>Peptides (chemistry)</term><term>Peptides (pharmacology)</term><term>Protease Inhibitors (chemical synthesis)</term><term>Protease Inhibitors (chemistry)</term><term>Protease Inhibitors (pharmacology)</term><term>Pyrrolidinones (chemical synthesis)</term><term>Pyrrolidinones (chemistry)</term><term>Pyrrolidinones (pharmacology)</term><term>SARS Virus</term><term>Structure-Activity Relationship</term><term>Thiazoles (chemical synthesis)</term><term>Thiazoles (chemistry)</term><term>Thiazoles (pharmacology)</term><term>Viral Proteins (antagonists & inhibitors)</term><term>Viral Proteins (metabolism)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="antagonists & inhibitors" xml:lang="en"><term>Chymases</term><term>Viral Proteins</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Antiviral Agents</term><term>Benzothiazoles</term><term>Ketones</term><term>Peptides</term><term>Protease Inhibitors</term><term>Pyrrolidinones</term><term>Thiazoles</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Antiviral Agents</term><term>Benzothiazoles</term><term>Ketones</term><term>Peptides</term><term>Protease Inhibitors</term><term>Pyrrolidinones</term><term>Thiazoles</term></keywords><keywords scheme="MESH" type="chemical" qualifier="metabolism" xml:lang="en"><term>Chymases</term><term>Cysteine Endopeptidases</term><term>Viral Proteins</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Antiviral Agents</term><term>Benzothiazoles</term><term>Peptides</term><term>Protease Inhibitors</term><term>Pyrrolidinones</term><term>Thiazoles</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Amino Acid Sequence</term><term>Computer Simulation</term><term>Drug Design</term><term>SARS Virus</term><term>Structure-Activity Relationship</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">A series of trifluoromethyl, benzothiazolyl or thiazolyl ketone-containing peptidic compounds as SARS-CoV 3CL protease inhibitors were developed and their potency was evaluated by in vitro protease inhibitory assays. Three candidates had encouraging results for the development of new anti-SARS compounds.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">19362479</PMID><DateCompleted><Year>2009</Year><Month>06</Month><Day>29</Day></DateCompleted><DateRevised><Year>2020</Year><Month>04</Month><Day>09</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1464-3405</ISSN><JournalIssue CitedMedium="Internet"><Volume>19</Volume><Issue>10</Issue><PubDate><Year>2009</Year><Month>May</Month><Day>15</Day></PubDate></JournalIssue><Title>Bioorganic & medicinal chemistry letters</Title><ISOAbbreviation>Bioorg. Med. Chem. Lett.</ISOAbbreviation></Journal><ArticleTitle>New developments for the design, synthesis and biological evaluation of potent SARS-CoV 3CL(pro) inhibitors.</ArticleTitle><Pagination><MedlinePgn>2722-7</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1016/j.bmcl.2009.03.118</ELocationID><Abstract><AbstractText>A series of trifluoromethyl, benzothiazolyl or thiazolyl ketone-containing peptidic compounds as SARS-CoV 3CL protease inhibitors were developed and their potency was evaluated by in vitro protease inhibitory assays. Three candidates had encouraging results for the development of new anti-SARS compounds.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Regnier</LastName><ForeName>Thomas</ForeName><Initials>T</Initials><AffiliationInfo><Affiliation>Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, Kyoto Pharmaceutical University, Japan.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Sarma</LastName><ForeName>Diganta</ForeName><Initials>D</Initials></Author><Author ValidYN="Y"><LastName>Hidaka</LastName><ForeName>Koushi</ForeName><Initials>K</Initials></Author><Author ValidYN="Y"><LastName>Bacha</LastName><ForeName>Usman</ForeName><Initials>U</Initials></Author><Author ValidYN="Y"><LastName>Freire</LastName><ForeName>Ernesto</ForeName><Initials>E</Initials></Author><Author ValidYN="Y"><LastName>Hayashi</LastName><ForeName>Yoshio</ForeName><Initials>Y</Initials></Author><Author ValidYN="Y"><LastName>Kiso</LastName><ForeName>Yoshiaki</ForeName><Initials>Y</Initials></Author></AuthorList><Language>eng</Language><GrantList CompleteYN="Y"><Grant><GrantID>P01 GM056550</GrantID><Acronym>GM</Acronym><Agency>NIGMS NIH HHS</Agency><Country>United States</Country></Grant><Grant><GrantID>R01 GM057144</GrantID><Acronym>GM</Acronym><Agency>NIGMS NIH HHS</Agency><Country>United States</Country></Grant><Grant><GrantID>GM 57144</GrantID><Acronym>GM</Acronym><Agency>NIGMS NIH HHS</Agency><Country>United States</Country></Grant></GrantList><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D052061">Research Support, N.I.H., Extramural</PublicationType><PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2009</Year><Month>03</Month><Day>28</Day></ArticleDate></Article><MedlineJournalInfo><Country>England</Country><MedlineTA>Bioorg Med Chem Lett</MedlineTA><NlmUniqueID>9107377</NlmUniqueID><ISSNLinking>0960-894X</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000998">Antiviral Agents</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D052160">Benzothiazoles</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D007659">Ketones</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D010455">Peptides</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D011480">Protease Inhibitors</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D011760">Pyrrolidinones</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D013844">Thiazoles</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance 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UI="D052160" MajorTopicYN="N">Benzothiazoles</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="N">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D053818" MajorTopicYN="N">Chymases</DescriptorName><QualifierName UI="Q000037" MajorTopicYN="N">antagonists & inhibitors</QualifierName><QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D003198" MajorTopicYN="N">Computer Simulation</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D003546" MajorTopicYN="N">Cysteine Endopeptidases</DescriptorName><QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D015195" MajorTopicYN="N">Drug Design</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D007659" MajorTopicYN="N">Ketones</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="N">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D010455" MajorTopicYN="N">Peptides</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="N">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D011480" MajorTopicYN="N">Protease Inhibitors</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="Y">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D011760" MajorTopicYN="N">Pyrrolidinones</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="N">chemical 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MajorTopicYN="N">metabolism</QualifierName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2009</Year><Month>02</Month><Day>24</Day></PubMedPubDate><PubMedPubDate PubStatus="revised"><Year>2009</Year><Month>03</Month><Day>24</Day></PubMedPubDate><PubMedPubDate PubStatus="accepted"><Year>2009</Year><Month>03</Month><Day>25</Day></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2009</Year><Month>4</Month><Day>14</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2009</Year><Month>4</Month><Day>14</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2009</Year><Month>6</Month><Day>30</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">19362479</ArticleId><ArticleId IdType="pii">S0960-894X(09)00455-7</ArticleId><ArticleId 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