New Potent SARS-CoV 3C-Like Protease Inhibitors Derived from Thieno[2,3-d]-pyrimidine Derivatives.
Identifieur interne : 002B88 ( Ncbi/Merge ); précédent : 002B87; suivant : 002B89New Potent SARS-CoV 3C-Like Protease Inhibitors Derived from Thieno[2,3-d]-pyrimidine Derivatives.
Auteurs : Amira S. Abd El-All [Égypte] ; Sanaa M Sh Atta [Égypte] ; Hanaa M F. Roaiah [Égypte] ; Enas M. Awad [Égypte] ; Mohamed M. Abdalla [Égypte]Source :
- Archiv der Pharmazie [ 1521-4184 ] ; 2016.
Descripteurs français
- KwdFr :
- Antiviraux (), Antiviraux (synthèse chimique), Cysteine endopeptidases (), Protéines virales (), Protéines virales (antagonistes et inhibiteurs), Pyrimidines (), Pyrimidines (synthèse chimique), Relation structure-activité, Sialidase (), Sialidase (antagonistes et inhibiteurs), Sous-type H3N2 du virus de la grippe A (enzymologie).
- MESH :
- antagonistes et inhibiteurs : Protéines virales, Sialidase.
- enzymologie : Sous-type H3N2 du virus de la grippe A.
- synthèse chimique : Antiviraux, Pyrimidines.
- Antiviraux, Cysteine endopeptidases, Protéines virales, Pyrimidines, Relation structure-activité, Sialidase.
English descriptors
- KwdEn :
- Antiviral Agents (chemical synthesis), Antiviral Agents (chemistry), Cysteine Endopeptidases (chemistry), Influenza A Virus, H3N2 Subtype (enzymology), Neuraminidase (antagonists & inhibitors), Neuraminidase (chemistry), Pyrimidines (chemical synthesis), Pyrimidines (chemistry), Structure-Activity Relationship, Viral Proteins (antagonists & inhibitors), Viral Proteins (chemistry).
- MESH :
- chemical , antagonists & inhibitors : Neuraminidase, Viral Proteins.
- chemical , chemical synthesis : Antiviral Agents, Pyrimidines.
- chemical , chemistry : Antiviral Agents, Cysteine Endopeptidases, Neuraminidase, Pyrimidines, Viral Proteins.
- enzymology : Influenza A Virus, H3N2 Subtype.
- Structure-Activity Relationship.
Abstract
2-Amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide (1) condensed with carbaldehydes 2a,b to give the respective thienopyrimidines (3a,b), which reacted with phosphoryl chloride and hydrazine hydrate to afford the respective pyrimidinohydrazines (4a,b). Compound 4a condensed with acetophenone under Vilsmeier conditions to afford the formylated pyrazolopyrimidine 6. Condensation of 4a with active methylenes produced the respective pyrazolopyrimidines (7-11). Besides, 4a condensed with succinic anhydride and with phthalic anhydride, yielding the pyrrolidine-2,5-dione 12 and the isoindoline-1,3-dione 13, respectively. Moreover, 4a reacted with isatin to afford the hydrazono-indolin-2-one 14. Structural elucidations for the new thienopyrimidines were based upon compatible analytical and spectroscopic results. Eleven of the new compounds were tested and found active against influenza A neuraminidase virus (H3N2). Compounds 12 and 13 were the most potent.
DOI: 10.1002/ardp.201500407
PubMed: 26806115
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Abd El-All</name><affiliation wicri:level="1"><nlm:affiliation>Department of Natural and Microbial Products, Research Division of Pharmaceutical and Drug Industries, National Research Centre, Dokki, Giza, Egypt.</nlm:affiliation><country xml:lang="fr">Égypte</country><wicri:regionArea>Department of Natural and Microbial Products, Research Division of Pharmaceutical and Drug Industries, National Research Centre, Dokki, Giza</wicri:regionArea><wicri:noRegion>Giza</wicri:noRegion></affiliation></author><author><name sortKey="Atta, Sanaa M Sh" sort="Atta, Sanaa M Sh" uniqKey="Atta S" first="Sanaa M Sh" last="Atta">Sanaa M Sh Atta</name><affiliation wicri:level="1"><nlm:affiliation>Department of Natural and Microbial Products, Research Division of Pharmaceutical and Drug Industries, National Research Centre, Dokki, Giza, Egypt.</nlm:affiliation><country xml:lang="fr">Égypte</country><wicri:regionArea>Department of Natural and Microbial Products, Research Division of Pharmaceutical and Drug Industries, National Research Centre, Dokki, Giza</wicri:regionArea><wicri:noRegion>Giza</wicri:noRegion></affiliation></author><author><name sortKey="Roaiah, Hanaa M F" sort="Roaiah, Hanaa M F" uniqKey="Roaiah H" first="Hanaa M F" last="Roaiah">Hanaa M F. Roaiah</name><affiliation wicri:level="1"><nlm:affiliation>Department of Natural and Microbial Products, Research Division of Pharmaceutical and Drug Industries, National Research Centre, Dokki, Giza, Egypt.</nlm:affiliation><country xml:lang="fr">Égypte</country><wicri:regionArea>Department of Natural and Microbial Products, Research Division of Pharmaceutical and Drug Industries, National Research Centre, Dokki, Giza</wicri:regionArea><wicri:noRegion>Giza</wicri:noRegion></affiliation></author><author><name sortKey="Awad, Enas M" sort="Awad, Enas M" uniqKey="Awad E" first="Enas M" last="Awad">Enas M. Awad</name><affiliation wicri:level="1"><nlm:affiliation>Department of Natural and Microbial Products, Research Division of Pharmaceutical and Drug Industries, National Research Centre, Dokki, Giza, Egypt.</nlm:affiliation><country xml:lang="fr">Égypte</country><wicri:regionArea>Department of Natural and Microbial Products, Research Division of Pharmaceutical and Drug Industries, National Research Centre, Dokki, Giza</wicri:regionArea><wicri:noRegion>Giza</wicri:noRegion></affiliation></author><author><name sortKey="Abdalla, Mohamed M" sort="Abdalla, Mohamed M" uniqKey="Abdalla M" first="Mohamed M" last="Abdalla">Mohamed M. Abdalla</name><affiliation wicri:level="1"><nlm:affiliation>Research Unit, Saco Pharm. Co., 6 October City, Egypt.</nlm:affiliation><country xml:lang="fr">Égypte</country><wicri:regionArea>Research Unit, Saco Pharm. Co., 6 October City</wicri:regionArea><wicri:noRegion>6 October City</wicri:noRegion></affiliation></author></analytic><series><title level="j">Archiv der Pharmazie</title><idno type="eISSN">1521-4184</idno><imprint><date when="2016" type="published">2016</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Antiviral Agents (chemical synthesis)</term><term>Antiviral Agents (chemistry)</term><term>Cysteine Endopeptidases (chemistry)</term><term>Influenza A Virus, H3N2 Subtype (enzymology)</term><term>Neuraminidase (antagonists & inhibitors)</term><term>Neuraminidase (chemistry)</term><term>Pyrimidines (chemical synthesis)</term><term>Pyrimidines (chemistry)</term><term>Structure-Activity Relationship</term><term>Viral Proteins (antagonists & inhibitors)</term><term>Viral Proteins (chemistry)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Antiviraux ()</term><term>Antiviraux (synthèse chimique)</term><term>Cysteine endopeptidases ()</term><term>Protéines virales ()</term><term>Protéines virales (antagonistes et inhibiteurs)</term><term>Pyrimidines ()</term><term>Pyrimidines (synthèse chimique)</term><term>Relation structure-activité</term><term>Sialidase ()</term><term>Sialidase (antagonistes et inhibiteurs)</term><term>Sous-type H3N2 du virus de la grippe A (enzymologie)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="antagonists & inhibitors" xml:lang="en"><term>Neuraminidase</term><term>Viral Proteins</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Antiviral Agents</term><term>Pyrimidines</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Antiviral Agents</term><term>Cysteine Endopeptidases</term><term>Neuraminidase</term><term>Pyrimidines</term><term>Viral Proteins</term></keywords><keywords scheme="MESH" qualifier="antagonistes et inhibiteurs" xml:lang="fr"><term>Protéines virales</term><term>Sialidase</term></keywords><keywords scheme="MESH" qualifier="enzymologie" xml:lang="fr"><term>Sous-type H3N2 du virus de la grippe A</term></keywords><keywords scheme="MESH" qualifier="enzymology" xml:lang="en"><term>Influenza A Virus, H3N2 Subtype</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Antiviraux</term><term>Pyrimidines</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Structure-Activity Relationship</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Antiviraux</term><term>Cysteine endopeptidases</term><term>Protéines virales</term><term>Pyrimidines</term><term>Relation structure-activité</term><term>Sialidase</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">2-Amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide (1) condensed with carbaldehydes 2a,b to give the respective thienopyrimidines (3a,b), which reacted with phosphoryl chloride and hydrazine hydrate to afford the respective pyrimidinohydrazines (4a,b). Compound 4a condensed with acetophenone under Vilsmeier conditions to afford the formylated pyrazolopyrimidine 6. Condensation of 4a with active methylenes produced the respective pyrazolopyrimidines (7-11). Besides, 4a condensed with succinic anhydride and with phthalic anhydride, yielding the pyrrolidine-2,5-dione 12 and the isoindoline-1,3-dione 13, respectively. Moreover, 4a reacted with isatin to afford the hydrazono-indolin-2-one 14. Structural elucidations for the new thienopyrimidines were based upon compatible analytical and spectroscopic results. Eleven of the new compounds were tested and found active against influenza A neuraminidase virus (H3N2). Compounds 12 and 13 were the most potent. </div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">26806115</PMID><DateCompleted><Year>2017</Year><Month>01</Month><Day>30</Day></DateCompleted><DateRevised><Year>2020</Year><Month>03</Month><Day>25</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1521-4184</ISSN><JournalIssue CitedMedium="Internet"><Volume>349</Volume><Issue>3</Issue><PubDate><Year>2016</Year><Month>Mar</Month></PubDate></JournalIssue><Title>Archiv der Pharmazie</Title><ISOAbbreviation>Arch. Pharm. (Weinheim)</ISOAbbreviation></Journal><ArticleTitle>New Potent SARS-CoV 3C-Like Protease Inhibitors Derived from Thieno[2,3-d]-pyrimidine Derivatives.</ArticleTitle><Pagination><MedlinePgn>202-10</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1002/ardp.201500407</ELocationID><Abstract><AbstractText>2-Amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide (1) condensed with carbaldehydes 2a,b to give the respective thienopyrimidines (3a,b), which reacted with phosphoryl chloride and hydrazine hydrate to afford the respective pyrimidinohydrazines (4a,b). Compound 4a condensed with acetophenone under Vilsmeier conditions to afford the formylated pyrazolopyrimidine 6. Condensation of 4a with active methylenes produced the respective pyrazolopyrimidines (7-11). Besides, 4a condensed with succinic anhydride and with phthalic anhydride, yielding the pyrrolidine-2,5-dione 12 and the isoindoline-1,3-dione 13, respectively. Moreover, 4a reacted with isatin to afford the hydrazono-indolin-2-one 14. Structural elucidations for the new thienopyrimidines were based upon compatible analytical and spectroscopic results. Eleven of the new compounds were tested and found active against influenza A neuraminidase virus (H3N2). Compounds 12 and 13 were the most potent. </AbstractText><CopyrightInformation>© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</CopyrightInformation></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Abd El-All</LastName><ForeName>Amira S</ForeName><Initials>AS</Initials><AffiliationInfo><Affiliation>Department of Natural and Microbial Products, Research Division of Pharmaceutical and Drug Industries, National Research Centre, Dokki, Giza, Egypt.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Atta</LastName><ForeName>Sanaa M Sh</ForeName><Initials>SM</Initials><AffiliationInfo><Affiliation>Department of Natural and Microbial Products, Research Division of Pharmaceutical and Drug Industries, National Research Centre, Dokki, Giza, Egypt.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Roaiah</LastName><ForeName>Hanaa M F</ForeName><Initials>HM</Initials><AffiliationInfo><Affiliation>Department of Natural and Microbial Products, Research Division of Pharmaceutical and Drug Industries, National Research Centre, Dokki, Giza, Egypt.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Awad</LastName><ForeName>Enas M</ForeName><Initials>EM</Initials><AffiliationInfo><Affiliation>Department of Natural and Microbial Products, Research Division of Pharmaceutical and Drug Industries, National Research Centre, Dokki, Giza, Egypt.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Abdalla</LastName><ForeName>Mohamed M</ForeName><Initials>MM</Initials><AffiliationInfo><Affiliation>Research Unit, Saco Pharm. Co., 6 October City, Egypt.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2016</Year><Month>01</Month><Day>25</Day></ArticleDate></Article><MedlineJournalInfo><Country>Germany</Country><MedlineTA>Arch Pharm (Weinheim)</MedlineTA><NlmUniqueID>0330167</NlmUniqueID><ISSNLinking>0365-6233</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000998">Antiviral Agents</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D011743">Pyrimidines</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D014764">Viral Proteins</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="C000601850">thieno(2,3-d)pyrimidine</NameOfSubstance></Chemical><Chemical><RegistryNumber>EC 3.2.1.18</RegistryNumber><NameOfSubstance UI="D009439">Neuraminidase</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></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D000998" MajorTopicYN="N">Antiviral Agents</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="N">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D003546" MajorTopicYN="Y">Cysteine Endopeptidases</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D053122" MajorTopicYN="N">Influenza A Virus, H3N2 Subtype</DescriptorName><QualifierName UI="Q000201" MajorTopicYN="N">enzymology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D009439" MajorTopicYN="N">Neuraminidase</DescriptorName><QualifierName UI="Q000037" MajorTopicYN="Y">antagonists & inhibitors</QualifierName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D011743" MajorTopicYN="N">Pyrimidines</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="N">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D013329" MajorTopicYN="N">Structure-Activity Relationship</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D014764" MajorTopicYN="N">Viral Proteins</DescriptorName><QualifierName UI="Q000037" MajorTopicYN="Y">antagonists & inhibitors</QualifierName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></MeshHeading></MeshHeadingList><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">Acid anhydrides</Keyword><Keyword MajorTopicYN="N">Active methylenes</Keyword><Keyword MajorTopicYN="N">Influenza virus (H3N2) inhibition</Keyword><Keyword MajorTopicYN="N">Structural elucidation</Keyword><Keyword MajorTopicYN="N">Tetrahydrobenzothienopyrimidines</Keyword></KeywordList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2015</Year><Month>11</Month><Day>12</Day></PubMedPubDate><PubMedPubDate PubStatus="revised"><Year>2015</Year><Month>12</Month><Day>22</Day></PubMedPubDate><PubMedPubDate PubStatus="accepted"><Year>2016</Year><Month>01</Month><Day>08</Day></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2016</Year><Month>1</Month><Day>26</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2016</Year><Month>1</Month><Day>26</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2017</Year><Month>1</Month><Day>31</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">26806115</ArticleId><ArticleId IdType="doi">10.1002/ardp.201500407</ArticleId></ArticleIdList></PubmedData></pubmed><affiliations><list><country><li>Égypte</li></country></list><tree><country name="Égypte"><noRegion><name sortKey="Abd El All, Amira S" sort="Abd El All, Amira S" uniqKey="Abd El All A" first="Amira S" last="Abd El-All">Amira S. Abd El-All</name></noRegion><name sortKey="Abdalla, Mohamed M" sort="Abdalla, Mohamed M" uniqKey="Abdalla M" first="Mohamed M" last="Abdalla">Mohamed M. Abdalla</name><name sortKey="Atta, Sanaa M Sh" sort="Atta, Sanaa M Sh" uniqKey="Atta S" first="Sanaa M Sh" last="Atta">Sanaa M Sh Atta</name><name sortKey="Awad, Enas M" sort="Awad, Enas M" uniqKey="Awad E" first="Enas M" last="Awad">Enas M. Awad</name><name sortKey="Roaiah, Hanaa M F" sort="Roaiah, Hanaa M F" uniqKey="Roaiah H" first="Hanaa M F" last="Roaiah">Hanaa M F. Roaiah</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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