H2N2V1, PubMed, Checkpoint, bibRecord, 000021

Highly potent activity of isopulegol-derived substituted octahydro-2H-chromen-4-ols against influenza A and B viruses.

Identifieur interne : 000021 ( PubMed/Checkpoint ); précédent : 000020; suivant : 000022

Highly potent activity of isopulegol-derived substituted octahydro-2H-chromen-4-ols against influenza A and B viruses.

Auteurs : Irina V. Ilyina [Russie] ; Vladimir V. Zarubaev [Russie] ; Irina N. Lavrentieva [Russie] ; Anna A. Shtro [Russie] ; Iana L. Esaulkova [Russie] ; Dina V. Korchagina [Russie] ; Sophia S. Borisevich [Russie] ; Konstantin P. Volcho [Russie] ; Nariman F. Salakhutdinov [Russie]

Source :

Bioorganic & medicinal chemistry letters [ 1464-3405 ] ; 2018.

RBID : pubmed:29716780

Descripteurs français

KwdFr :
- Antiviraux (), Antiviraux (pharmacologie), Antiviraux (synthèse chimique), Relation dose-effet des médicaments, Relation structure-activité, Structure moléculaire, Terpènes (), Terpènes (pharmacologie), Terpènes (synthèse chimique), Tests de sensibilité microbienne, Virus de la grippe A (), Virus influenza B ().
MESH :
- pharmacologie : Antiviraux, Terpènes.
- synthèse chimique : Antiviraux, Terpènes.
- Antiviraux, Relation dose-effet des médicaments, Relation structure-activité, Structure moléculaire, Terpènes, Tests de sensibilité microbienne, Virus de la grippe A, Virus influenza B.

English descriptors

KwdEn :
- Antiviral Agents (chemical synthesis), Antiviral Agents (chemistry), Antiviral Agents (pharmacology), Cyclohexane Monoterpenes, Dose-Response Relationship, Drug, Influenza A virus (drug effects), Influenza B virus (drug effects), Microbial Sensitivity Tests, Molecular Structure, Structure-Activity Relationship, Terpenes (chemical synthesis), Terpenes (chemistry), Terpenes (pharmacology).
MESH :
- chemical , chemical synthesis : Antiviral Agents, Terpenes.
- chemical , chemistry : Antiviral Agents, Terpenes.
- chemical , pharmacology : Antiviral Agents, Terpenes.
- chemical : Cyclohexane Monoterpenes.
- drug effects : Influenza A virus, Influenza B virus.
- Dose-Response Relationship, Drug, Microbial Sensitivity Tests, Molecular Structure, Structure-Activity Relationship.

Abstract

A set of (-)-isopulegol derived octahydro-2H-chromen-4-ols was synthesized and evaluated in vitro for antiviral activity against panel of reference influenza virus strains differing in subtype, origin (human or avian) and drug resistance. Compound (4R)-11a produced via one-pot synthesis by interaction between (-)-isopulegol and acetone was found to exhibit an outstanding activity against a number of H1N1 and H2N2 influenza virus strains with selectivity index more than 1500. (4R)-11a was shown to be most potent at early stages of viral cycle. Good correlation between anti-viral activity and calculated binding energy to hemagglutinin TBHQ active site was demonstrated.

DOI: 10.1016/j.bmcl.2018.04.057
PubMed: 29716780

Affiliations:

Russie

Links toward previous steps (curation, corpus...)

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pubmed:29716780

Le document en format XML

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<front><div type="abstract" xml:lang="en">A set of (-)-isopulegol derived octahydro-2H-chromen-4-ols was synthesized and evaluated in vitro for antiviral activity against panel of reference influenza virus strains differing in subtype, origin (human or avian) and drug resistance. Compound (4R)-11a produced via one-pot synthesis by interaction between (-)-isopulegol and acetone was found to exhibit an outstanding activity against a number of H1N1 and H2N2 influenza virus strains with selectivity index more than 1500. (4R)-11a was shown to be most potent at early stages of viral cycle. Good correlation between anti-viral activity and calculated binding energy to hemagglutinin TBHQ active site was demonstrated.</div>
</front>
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<ArticleTitle>Highly potent activity of isopulegol-derived substituted octahydro-2H-chromen-4-ols against influenza A and B viruses.</ArticleTitle>
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<Abstract><AbstractText>A set of (-)-isopulegol derived octahydro-2H-chromen-4-ols was synthesized and evaluated in vitro for antiviral activity against panel of reference influenza virus strains differing in subtype, origin (human or avian) and drug resistance. Compound (4R)-11a produced via one-pot synthesis by interaction between (-)-isopulegol and acetone was found to exhibit an outstanding activity against a number of H1N1 and H2N2 influenza virus strains with selectivity index more than 1500. (4R)-11a was shown to be most potent at early stages of viral cycle. Good correlation between anti-viral activity and calculated binding energy to hemagglutinin TBHQ active site was demonstrated.</AbstractText>
<CopyrightInformation>Copyright © 2018 Elsevier Ltd. All rights reserved.</CopyrightInformation>
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<AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Ilyina</LastName>
<ForeName>Irina V</ForeName>
<Initials>IV</Initials>
<AffiliationInfo><Affiliation>Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Lavrentjev av.9, 630090 Novosibirsk, Russian Federation; Novosibirsk State University, Pirogova 2, Novosibirsk 630090, Russian Federation.</Affiliation>
</AffiliationInfo>
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</AffiliationInfo>
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<Author ValidYN="Y"><LastName>Lavrentieva</LastName>
<ForeName>Irina N</ForeName>
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<AffiliationInfo><Affiliation>Pasteur Institute of Epidemiology and Microbiology, 14 Mira str., 197101 St. Petersburg, Russian Federation.</Affiliation>
</AffiliationInfo>
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</AffiliationInfo>
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<Initials>IL</Initials>
<AffiliationInfo><Affiliation>Saint Petersburg State University, 7/9 Universitetskaya nab., 199034 St. Petersburg, Russian Federation.</Affiliation>
</AffiliationInfo>
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<Author ValidYN="Y"><LastName>Korchagina</LastName>
<ForeName>Dina V</ForeName>
<Initials>DV</Initials>
<AffiliationInfo><Affiliation>Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Lavrentjev av.9, 630090 Novosibirsk, Russian Federation.</Affiliation>
</AffiliationInfo>
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<Author ValidYN="Y"><LastName>Borisevich</LastName>
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<Initials>KP</Initials>
<AffiliationInfo><Affiliation>Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Lavrentjev av.9, 630090 Novosibirsk, Russian Federation; Novosibirsk State University, Pirogova 2, Novosibirsk 630090, Russian Federation. Electronic address: volcho@nioch.nsc.ru.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Salakhutdinov</LastName>
<ForeName>Nariman F</ForeName>
<Initials>NF</Initials>
<AffiliationInfo><Affiliation>Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Lavrentjev av.9, 630090 Novosibirsk, Russian Federation; Novosibirsk State University, Pirogova 2, Novosibirsk 630090, Russian Federation.</Affiliation>
</AffiliationInfo>
</Author>
</AuthorList>
<Language>eng</Language>
<PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType>
<PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType>
</PublicationTypeList>
<ArticleDate DateType="Electronic"><Year>2018</Year>
<Month>04</Month>
<Day>24</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="D000081005">Cyclohexane Monoterpenes</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D013729">Terpenes</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>3TH92O3BXN</RegistryNumber>
<NameOfSubstance UI="C409816">isopulegol</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="N">chemistry</QualifierName>
<QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D000081005" MajorTopicYN="N">Cyclohexane Monoterpenes</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D004305" MajorTopicYN="N">Dose-Response Relationship, Drug</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D009980" MajorTopicYN="N">Influenza A virus</DescriptorName>
<QualifierName UI="Q000187" MajorTopicYN="Y">drug effects</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D009981" MajorTopicYN="N">Influenza B virus</DescriptorName>
<QualifierName UI="Q000187" MajorTopicYN="Y">drug effects</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D008826" MajorTopicYN="N">Microbial Sensitivity Tests</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D015394" MajorTopicYN="N">Molecular Structure</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D013329" MajorTopicYN="N">Structure-Activity Relationship</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D013729" MajorTopicYN="N">Terpenes</DescriptorName>
<QualifierName UI="Q000138" MajorTopicYN="N">chemical synthesis</QualifierName>
<QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName>
<QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName>
</MeshHeading>
</MeshHeadingList>
<KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="Y">Antiviral</Keyword>
<Keyword MajorTopicYN="Y">Chromene</Keyword>
<Keyword MajorTopicYN="Y">Influenza</Keyword>
<Keyword MajorTopicYN="Y">Monoterpene</Keyword>
<Keyword MajorTopicYN="Y">Montmorillonite K10</Keyword>
</KeywordList>
</MedlineCitation>
<PubmedData><History><PubMedPubDate PubStatus="received"><Year>2018</Year>
<Month>03</Month>
<Day>14</Day>
</PubMedPubDate>
<PubMedPubDate PubStatus="revised"><Year>2018</Year>
<Month>04</Month>
<Day>19</Day>
</PubMedPubDate>
<PubMedPubDate PubStatus="accepted"><Year>2018</Year>
<Month>04</Month>
<Day>23</Day>
</PubMedPubDate>
<PubMedPubDate PubStatus="pubmed"><Year>2018</Year>
<Month>5</Month>
<Day>3</Day>
<Hour>6</Hour>
<Minute>0</Minute>
</PubMedPubDate>
<PubMedPubDate PubStatus="medline"><Year>2019</Year>
<Month>1</Month>
<Day>23</Day>
<Hour>6</Hour>
<Minute>0</Minute>
</PubMedPubDate>
<PubMedPubDate PubStatus="entrez"><Year>2018</Year>
<Month>5</Month>
<Day>3</Day>
<Hour>6</Hour>
<Minute>0</Minute>
</PubMedPubDate>
</History>
<PublicationStatus>ppublish</PublicationStatus>
<ArticleIdList><ArticleId IdType="pubmed">29716780</ArticleId>
<ArticleId IdType="pii">S0960-894X(18)30369-X</ArticleId>
<ArticleId IdType="doi">10.1016/j.bmcl.2018.04.057</ArticleId>
</ArticleIdList>
</PubmedData>
</pubmed>
<affiliations><list><country><li>Russie</li>
</country>
</list>
<tree><country name="Russie"><noRegion><name sortKey="Ilyina, Irina V" sort="Ilyina, Irina V" uniqKey="Ilyina I" first="Irina V" last="Ilyina">Irina V. Ilyina</name>
</noRegion>
<name sortKey="Borisevich, Sophia S" sort="Borisevich, Sophia S" uniqKey="Borisevich S" first="Sophia S" last="Borisevich">Sophia S. Borisevich</name>
<name sortKey="Esaulkova, Iana L" sort="Esaulkova, Iana L" uniqKey="Esaulkova I" first="Iana L" last="Esaulkova">Iana L. Esaulkova</name>
<name sortKey="Korchagina, Dina V" sort="Korchagina, Dina V" uniqKey="Korchagina D" first="Dina V" last="Korchagina">Dina V. Korchagina</name>
<name sortKey="Lavrentieva, Irina N" sort="Lavrentieva, Irina N" uniqKey="Lavrentieva I" first="Irina N" last="Lavrentieva">Irina N. Lavrentieva</name>
<name sortKey="Salakhutdinov, Nariman F" sort="Salakhutdinov, Nariman F" uniqKey="Salakhutdinov N" first="Nariman F" last="Salakhutdinov">Nariman F. Salakhutdinov</name>
<name sortKey="Shtro, Anna A" sort="Shtro, Anna A" uniqKey="Shtro A" first="Anna A" last="Shtro">Anna A. Shtro</name>
<name sortKey="Volcho, Konstantin P" sort="Volcho, Konstantin P" uniqKey="Volcho K" first="Konstantin P" last="Volcho">Konstantin P. Volcho</name>
<name sortKey="Zarubaev, Vladimir V" sort="Zarubaev, Vladimir V" uniqKey="Zarubaev V" first="Vladimir V" last="Zarubaev">Vladimir V. Zarubaev</name>
</country>
</tree>
</affiliations>
</record>

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Highly potent activity of isopulegol-derived substituted octahydro-2H-chromen-4-ols against influenza A and B viruses.

Highly potent activity of isopulegol-derived substituted octahydro-2H-chromen-4-ols against influenza A and B viruses.

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