Synthesis and evaluation of isatin derivatives as effective SARS coronavirus 3CL protease inhibitors.
Identifieur interne : 002736 ( PubMed/Corpus ); précédent : 002735; suivant : 002737Synthesis and evaluation of isatin derivatives as effective SARS coronavirus 3CL protease inhibitors.
Auteurs : Li-Rung Chen ; Yu-Chin Wang ; Yi Wen Lin ; Shan-Yen Chou ; Shyh-Fong Chen ; Lee Tai Liu ; Ying-Ta Wu ; Chih-Jung Kuo ; Tom Shieh-Shung Chen ; Shin-Hun JuangSource :
- Bioorganic & medicinal chemistry letters [ 0960-894X ] ; 2005.
English descriptors
- KwdEn :
- Binding Sites, Chymotrypsin (pharmacology), Computer Simulation, Cysteine Endopeptidases, Endopeptidases, Enzyme Activation, Fluorescence Resonance Energy Transfer, Humans, Isatin (analogs & derivatives), Isatin (chemical synthesis), Isatin (pharmacology), Molecular Structure, Papain (pharmacology), Protease Inhibitors (chemical synthesis), Protease Inhibitors (chemistry), Protease Inhibitors (pharmacology), SARS Virus (enzymology), Structure-Activity Relationship, Substrate Specificity, Trypsin (pharmacology), Viral Proteins (antagonists & inhibitors).
- MESH :
- chemical , analogs & derivatives : Isatin.
- chemical , antagonists & inhibitors : Viral Proteins.
- chemical , chemical synthesis : Isatin, Protease Inhibitors.
- chemical , chemistry : Protease Inhibitors.
- chemical , pharmacology : Chymotrypsin, Isatin, Papain, Protease Inhibitors, Trypsin.
- enzymology : SARS Virus.
- Binding Sites, Computer Simulation, Cysteine Endopeptidases, Endopeptidases, Enzyme Activation, Fluorescence Resonance Energy Transfer, Humans, Molecular Structure, Structure-Activity Relationship, Substrate Specificity.
Abstract
N-Substituted isatin derivatives were prepared from the reaction of isatin and various bromides via two steps. Bioactivity assay results (in vitro tests) demonstrated that some of these compounds are potent and selective inhibitors against SARS coronavirus 3CL protease with IC50 values ranging from 0.95 to 17.50 microM. Additionally, isatin 4o exhibited more potent inhibition for SARS coronavirus protease than for other proteases including papain, chymotrypsin, and trypsin.
DOI: 10.1016/j.bmcl.2005.04.027
PubMed: 15896959
Links to Exploration step
pubmed:15896959Le document en format XML
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Chen</name></author><author><name sortKey="Liu, Lee Tai" sort="Liu, Lee Tai" uniqKey="Liu L" first="Lee Tai" last="Liu">Lee Tai Liu</name></author><author><name sortKey="Wu, Ying Ta" sort="Wu, Ying Ta" uniqKey="Wu Y" first="Ying-Ta" last="Wu">Ying-Ta Wu</name></author><author><name sortKey="Kuo, Chih Jung" sort="Kuo, Chih Jung" uniqKey="Kuo C" first="Chih-Jung" last="Kuo">Chih-Jung Kuo</name></author><author><name sortKey="Chen, Tom Shieh Shung" sort="Chen, Tom Shieh Shung" uniqKey="Chen T" first="Tom Shieh-Shung" last="Chen">Tom Shieh-Shung Chen</name></author><author><name sortKey="Juang, Shin Hun" sort="Juang, Shin Hun" uniqKey="Juang S" first="Shin-Hun" last="Juang">Shin-Hun Juang</name></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2005">2005</date><idno type="RBID">pubmed:15896959</idno><idno type="pmid">15896959</idno><idno type="doi">10.1016/j.bmcl.2005.04.027</idno><idno type="wicri:Area/PubMed/Corpus">002736</idno><idno 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Fong" sort="Chen, Shyh Fong" uniqKey="Chen S" first="Shyh-Fong" last="Chen">Shyh-Fong Chen</name></author><author><name sortKey="Liu, Lee Tai" sort="Liu, Lee Tai" uniqKey="Liu L" first="Lee Tai" last="Liu">Lee Tai Liu</name></author><author><name sortKey="Wu, Ying Ta" sort="Wu, Ying Ta" uniqKey="Wu Y" first="Ying-Ta" last="Wu">Ying-Ta Wu</name></author><author><name sortKey="Kuo, Chih Jung" sort="Kuo, Chih Jung" uniqKey="Kuo C" first="Chih-Jung" last="Kuo">Chih-Jung Kuo</name></author><author><name sortKey="Chen, Tom Shieh Shung" sort="Chen, Tom Shieh Shung" uniqKey="Chen T" first="Tom Shieh-Shung" last="Chen">Tom Shieh-Shung Chen</name></author><author><name sortKey="Juang, Shin Hun" sort="Juang, Shin Hun" uniqKey="Juang S" first="Shin-Hun" last="Juang">Shin-Hun Juang</name></author></analytic><series><title level="j">Bioorganic & medicinal chemistry letters</title><idno type="ISSN">0960-894X</idno><imprint><date when="2005" type="published">2005</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Binding Sites</term><term>Chymotrypsin (pharmacology)</term><term>Computer Simulation</term><term>Cysteine Endopeptidases</term><term>Endopeptidases</term><term>Enzyme Activation</term><term>Fluorescence Resonance Energy Transfer</term><term>Humans</term><term>Isatin (analogs & derivatives)</term><term>Isatin (chemical synthesis)</term><term>Isatin (pharmacology)</term><term>Molecular Structure</term><term>Papain (pharmacology)</term><term>Protease Inhibitors (chemical synthesis)</term><term>Protease Inhibitors (chemistry)</term><term>Protease Inhibitors (pharmacology)</term><term>SARS Virus (enzymology)</term><term>Structure-Activity Relationship</term><term>Substrate Specificity</term><term>Trypsin (pharmacology)</term><term>Viral Proteins (antagonists & inhibitors)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="analogs & derivatives" xml:lang="en"><term>Isatin</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>Isatin</term><term>Protease Inhibitors</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Protease Inhibitors</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Chymotrypsin</term><term>Isatin</term><term>Papain</term><term>Protease Inhibitors</term><term>Trypsin</term></keywords><keywords scheme="MESH" qualifier="enzymology" xml:lang="en"><term>SARS Virus</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Binding Sites</term><term>Computer Simulation</term><term>Cysteine Endopeptidases</term><term>Endopeptidases</term><term>Enzyme Activation</term><term>Fluorescence Resonance Energy Transfer</term><term>Humans</term><term>Molecular Structure</term><term>Structure-Activity Relationship</term><term>Substrate Specificity</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">N-Substituted isatin derivatives were prepared from the reaction of isatin and various bromides via two steps. Bioactivity assay results (in vitro tests) demonstrated that some of these compounds are potent and selective inhibitors against SARS coronavirus 3CL protease with IC50 values ranging from 0.95 to 17.50 microM. Additionally, isatin 4o exhibited more potent inhibition for SARS coronavirus protease than for other proteases including papain, chymotrypsin, and trypsin.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">15896959</PMID><DateCompleted><Year>2005</Year><Month>09</Month><Day>19</Day></DateCompleted><DateRevised><Year>2020</Year><Month>04</Month><Day>04</Day></DateRevised><Article PubModel="Print"><Journal><ISSN IssnType="Print">0960-894X</ISSN><JournalIssue CitedMedium="Print"><Volume>15</Volume><Issue>12</Issue><PubDate><Year>2005</Year><Month>Jun</Month><Day>15</Day></PubDate></JournalIssue><Title>Bioorganic & medicinal chemistry letters</Title><ISOAbbreviation>Bioorg. Med. Chem. Lett.</ISOAbbreviation></Journal><ArticleTitle>Synthesis and evaluation of isatin derivatives as effective SARS coronavirus 3CL protease inhibitors.</ArticleTitle><Pagination><MedlinePgn>3058-62</MedlinePgn></Pagination><Abstract><AbstractText>N-Substituted isatin derivatives were prepared from the reaction of isatin and various bromides via two steps. Bioactivity assay results (in vitro tests) demonstrated that some of these compounds are potent and selective inhibitors against SARS coronavirus 3CL protease with IC50 values ranging from 0.95 to 17.50 microM. Additionally, isatin 4o exhibited more potent inhibition for SARS coronavirus protease than for other proteases including papain, chymotrypsin, and trypsin.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Chen</LastName><ForeName>Li-Rung</ForeName><Initials>LR</Initials><AffiliationInfo><Affiliation>Development Center for Biotechnology, 102, Lane 169, Kang Ning St., Xi Zhi 221, Taipei, Taiwan, ROC.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Wang</LastName><ForeName>Yu-Chin</ForeName><Initials>YC</Initials></Author><Author ValidYN="Y"><LastName>Lin</LastName><ForeName>Yi Wen</ForeName><Initials>YW</Initials></Author><Author ValidYN="Y"><LastName>Chou</LastName><ForeName>Shan-Yen</ForeName><Initials>SY</Initials></Author><Author ValidYN="Y"><LastName>Chen</LastName><ForeName>Shyh-Fong</ForeName><Initials>SF</Initials></Author><Author ValidYN="Y"><LastName>Liu</LastName><ForeName>Lee Tai</ForeName><Initials>LT</Initials></Author><Author ValidYN="Y"><LastName>Wu</LastName><ForeName>Ying-Ta</ForeName><Initials>YT</Initials></Author><Author ValidYN="Y"><LastName>Kuo</LastName><ForeName>Chih-Jung</ForeName><Initials>CJ</Initials></Author><Author ValidYN="Y"><LastName>Chen</LastName><ForeName>Tom Shieh-Shung</ForeName><Initials>TS</Initials></Author><Author ValidYN="Y"><LastName>Juang</LastName><ForeName>Shin-Hun</ForeName><Initials>SH</Initials></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D003160">Comparative Study</PublicationType><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType></PublicationTypeList></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="D011480">Protease Inhibitors</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D014764">Viral Proteins</NameOfSubstance></Chemical><Chemical><RegistryNumber>82X95S7M06</RegistryNumber><NameOfSubstance UI="D007510">Isatin</NameOfSubstance></Chemical><Chemical><RegistryNumber>EC 3.4.-</RegistryNumber><NameOfSubstance UI="D010450">Endopeptidases</NameOfSubstance></Chemical><Chemical><RegistryNumber>EC 3.4.21.1</RegistryNumber><NameOfSubstance UI="D002918">Chymotrypsin</NameOfSubstance></Chemical><Chemical><RegistryNumber>EC 3.4.21.4</RegistryNumber><NameOfSubstance UI="D014357">Trypsin</NameOfSubstance></Chemical><Chemical><RegistryNumber>EC 3.4.22.-</RegistryNumber><NameOfSubstance UI="C099456">3C-like proteinase, Coronavirus</NameOfSubstance></Chemical><Chemical><RegistryNumber>EC 3.4.22.-</RegistryNumber><NameOfSubstance UI="D003546">Cysteine Endopeptidases</NameOfSubstance></Chemical><Chemical><RegistryNumber>EC 3.4.22.2</RegistryNumber><NameOfSubstance UI="D010206">Papain</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D001665" MajorTopicYN="N">Binding Sites</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D002918" MajorTopicYN="N">Chymotrypsin</DescriptorName><QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D003198" MajorTopicYN="N">Computer Simulation</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D003546" MajorTopicYN="N">Cysteine Endopeptidases</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D010450" MajorTopicYN="N">Endopeptidases</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D004789" MajorTopicYN="N">Enzyme Activation</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D031541" MajorTopicYN="N">Fluorescence Resonance Energy Transfer</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D006801" MajorTopicYN="N">Humans</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D007510" MajorTopicYN="N">Isatin</DescriptorName><QualifierName UI="Q000031" MajorTopicYN="Y">analogs & derivatives</QualifierName><QualifierName UI="Q000138" MajorTopicYN="N">chemical synthesis</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D015394" MajorTopicYN="N">Molecular Structure</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D010206" MajorTopicYN="N">Papain</DescriptorName><QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D011480" MajorTopicYN="N">Protease 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