Antiviral agents derived from novel 1-adamantyl singlet nitrenes.
Identifieur interne : 001386 ( PubMed/Checkpoint ); précédent : 001385; suivant : 001387Antiviral agents derived from novel 1-adamantyl singlet nitrenes.
Auteurs : Andreas J. Kesel [Allemagne] ; Hans-Christoph Weiss ; Andreas Schönleber ; Craig W. Day ; Dale L. Barnard ; Mervi A. Detorio ; Raymond F. SchinaziSource :
- Antiviral chemistry & chemotherapy [ 2040-2066 ] ; 2012.
Descripteurs français
- KwdFr :
- Amantadine (analogues et dérivés), Amantadine (pharmacologie), Antiviraux (), Antiviraux (pharmacologie), Cellules cultivées, Cristallographie aux rayons X, Grippe humaine (traitement médicamenteux), Humains, Imines (), Imines (pharmacologie), Infections à respirovirus (traitement médicamenteux), Modèles moléculaires, Syndrome respiratoire aigu sévère (traitement médicamenteux), VIH-1 (Virus de l'Immunodéficience Humaine de type 1) (), Virus de la grippe A (), Virus du SRAS (), Virus influenza B (), Virus parainfluenza humain de type 3 ().
- MESH :
- analogues et dérivés : Amantadine.
- pharmacologie : Amantadine, Antiviraux, Imines.
- traitement médicamenteux : Grippe humaine, Infections à respirovirus, Syndrome respiratoire aigu sévère.
- Antiviraux, Cellules cultivées, Cristallographie aux rayons X, Humains, Imines, Modèles moléculaires, VIH-1 (Virus de l'Immunodéficience Humaine de type 1), Virus de la grippe A, Virus du SRAS, Virus influenza B, Virus parainfluenza humain de type 3.
English descriptors
- KwdEn :
- Amantadine (analogs & derivatives), Amantadine (pharmacology), Antiviral Agents (chemistry), Antiviral Agents (pharmacology), Cells, Cultured, Crystallography, X-Ray, HIV-1 (drug effects), Humans, Imines (chemistry), Imines (pharmacology), Influenza A virus (drug effects), Influenza B virus (drug effects), Influenza, Human (drug therapy), Models, Molecular, Parainfluenza Virus 3, Human (drug effects), Respirovirus Infections (drug therapy), SARS Virus (drug effects), Severe Acute Respiratory Syndrome (drug therapy).
- MESH :
- chemical , analogs & derivatives : Amantadine.
- chemical , chemistry : Antiviral Agents, Imines.
- chemical , pharmacology : Amantadine, Antiviral Agents, Imines.
- drug effects : HIV-1, Influenza A virus, Influenza B virus, Parainfluenza Virus 3, Human, SARS Virus.
- drug therapy : Influenza, Human, Respirovirus Infections, Severe Acute Respiratory Syndrome.
- Cells, Cultured, Crystallography, X-Ray, Humans, Models, Molecular.
Abstract
Amantadine constitutes an interesting, diamond crystal lattice-shaped, antivirally active amine with an inhibitory effect on influenza A viruses causing common 'flu' in humans. Unfortunately, amantadine forfeited most of its therapeutic potential because of resistance development in recent influenza A virus isolates. The antiviral efficacy of amantadine congeners can be chemically modified, resulting in re-constitution, improvement and/or extension of antiviral activities mediated by amino-adamantyls.
DOI: 10.3851/IMP2485
PubMed: 23234699
Affiliations:
Links toward previous steps (curation, corpus...)
Links to Exploration step
pubmed:23234699Le document en format XML
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<term>Amantadine (pharmacology)</term>
<term>Antiviral Agents (chemistry)</term>
<term>Antiviral Agents (pharmacology)</term>
<term>Cells, Cultured</term>
<term>Crystallography, X-Ray</term>
<term>HIV-1 (drug effects)</term>
<term>Humans</term>
<term>Imines (chemistry)</term>
<term>Imines (pharmacology)</term>
<term>Influenza A virus (drug effects)</term>
<term>Influenza B virus (drug effects)</term>
<term>Influenza, Human (drug therapy)</term>
<term>Models, Molecular</term>
<term>Parainfluenza Virus 3, Human (drug effects)</term>
<term>Respirovirus Infections (drug therapy)</term>
<term>SARS Virus (drug effects)</term>
<term>Severe Acute Respiratory Syndrome (drug therapy)</term>
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<keywords scheme="KwdFr" xml:lang="fr"><term>Amantadine (analogues et dérivés)</term>
<term>Amantadine (pharmacologie)</term>
<term>Antiviraux ()</term>
<term>Antiviraux (pharmacologie)</term>
<term>Cellules cultivées</term>
<term>Cristallographie aux rayons X</term>
<term>Grippe humaine (traitement médicamenteux)</term>
<term>Humains</term>
<term>Imines ()</term>
<term>Imines (pharmacologie)</term>
<term>Infections à respirovirus (traitement médicamenteux)</term>
<term>Modèles moléculaires</term>
<term>Syndrome respiratoire aigu sévère (traitement médicamenteux)</term>
<term>VIH-1 (Virus de l'Immunodéficience Humaine de type 1) ()</term>
<term>Virus de la grippe A ()</term>
<term>Virus du SRAS ()</term>
<term>Virus influenza B ()</term>
<term>Virus parainfluenza humain de type 3 ()</term>
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<term>Imines</term>
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<term>Antiviral Agents</term>
<term>Imines</term>
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<keywords scheme="MESH" qualifier="analogues et dérivés" xml:lang="fr"><term>Amantadine</term>
</keywords>
<keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>HIV-1</term>
<term>Influenza A virus</term>
<term>Influenza B virus</term>
<term>Parainfluenza Virus 3, Human</term>
<term>SARS Virus</term>
</keywords>
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<term>Respirovirus Infections</term>
<term>Severe Acute Respiratory Syndrome</term>
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<keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Amantadine</term>
<term>Antiviraux</term>
<term>Imines</term>
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<keywords scheme="MESH" qualifier="traitement médicamenteux" xml:lang="fr"><term>Grippe humaine</term>
<term>Infections à respirovirus</term>
<term>Syndrome respiratoire aigu sévère</term>
</keywords>
<keywords scheme="MESH" xml:lang="en"><term>Cells, Cultured</term>
<term>Crystallography, X-Ray</term>
<term>Humans</term>
<term>Models, Molecular</term>
</keywords>
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<term>Cellules cultivées</term>
<term>Cristallographie aux rayons X</term>
<term>Humains</term>
<term>Imines</term>
<term>Modèles moléculaires</term>
<term>VIH-1 (Virus de l'Immunodéficience Humaine de type 1)</term>
<term>Virus de la grippe A</term>
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<term>Virus influenza B</term>
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<front><div type="abstract" xml:lang="en">Amantadine constitutes an interesting, diamond crystal lattice-shaped, antivirally active amine with an inhibitory effect on influenza A viruses causing common 'flu' in humans. Unfortunately, amantadine forfeited most of its therapeutic potential because of resistance development in recent influenza A virus isolates. The antiviral efficacy of amantadine congeners can be chemically modified, resulting in re-constitution, improvement and/or extension of antiviral activities mediated by amino-adamantyls.</div>
</front>
</TEI>
<pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">23234699</PMID>
<DateCompleted><Year>2014</Year>
<Month>07</Month>
<Day>09</Day>
</DateCompleted>
<DateRevised><Year>2013</Year>
<Month>12</Month>
<Day>11</Day>
</DateRevised>
<Article PubModel="Electronic"><Journal><ISSN IssnType="Electronic">2040-2066</ISSN>
<JournalIssue CitedMedium="Internet"><Volume>23</Volume>
<Issue>3</Issue>
<PubDate><Year>2012</Year>
<Month>Dec</Month>
<Day>07</Day>
</PubDate>
</JournalIssue>
<Title>Antiviral chemistry & chemotherapy</Title>
<ISOAbbreviation>Antivir. Chem. Chemother.</ISOAbbreviation>
</Journal>
<ArticleTitle>Antiviral agents derived from novel 1-adamantyl singlet nitrenes.</ArticleTitle>
<Pagination><MedlinePgn>113-28</MedlinePgn>
</Pagination>
<ELocationID EIdType="doi" ValidYN="Y">10.3851/IMP2485</ELocationID>
<Abstract><AbstractText Label="BACKGROUND" NlmCategory="BACKGROUND">Amantadine constitutes an interesting, diamond crystal lattice-shaped, antivirally active amine with an inhibitory effect on influenza A viruses causing common 'flu' in humans. Unfortunately, amantadine forfeited most of its therapeutic potential because of resistance development in recent influenza A virus isolates. The antiviral efficacy of amantadine congeners can be chemically modified, resulting in re-constitution, improvement and/or extension of antiviral activities mediated by amino-adamantyls.</AbstractText>
<AbstractText Label="METHODS" NlmCategory="METHODS">Newly synthesized compounds were evaluated towards HIV type-1 (HIV-1) replication in primary human lymphocytes. One N-phenacyl amantadine derivative was investigated for inhibiting the in vitro replication of respiratory viruses (influenza A viruses, influenza B virus, human parainfluenza virus type 3 and severe acute respiratory syndrome coronavirus).</AbstractText>
<AbstractText Label="RESULTS" NlmCategory="RESULTS">Two ketone-stabilized 1-adamantyl singlet nitrenes were discovered serendipitously. To our best knowledge these are the first persistently stable nitrenes to be reported. Their structure was proved by determining the X-ray single crystal structure of one hydrolytic elaboration product. This salt adduct revealed an incommensurately modulated crystal structure, which was solved by extensive computational refinement. We could show that ketone-stabilized 1-adamantyl singlet nitrenes are versatile synthons for the synthesis of antiviral drug candidates. An amantadine-folate conjugate was inhibitory on HIV-1 replication in primary human lymphocytes, and one N-phenacyl amantadine derivative was inhibitory towards low pathogenic avian influenza A virus (H5N1) replication in vitro.</AbstractText>
<AbstractText Label="CONCLUSIONS" NlmCategory="CONCLUSIONS">These results indicate that the aromatic-aliphatic ketone-stabilized 1-adamantyl singlet nitrenes, beyond being of fundamental interest in organic chemistry, represent versatile synthons for the synthesis of new amantadine-related potentially antiviral drugs.</AbstractText>
</Abstract>
<AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Kesel</LastName>
<ForeName>Andreas J</ForeName>
<Initials>AJ</Initials>
<AffiliationInfo><Affiliation>Chammünsterstr 47, Munich, Germany. andreas.kesel@gmx.de.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Weiss</LastName>
<ForeName>Hans-Christoph</ForeName>
<Initials>HC</Initials>
</Author>
<Author ValidYN="Y"><LastName>Schönleber</LastName>
<ForeName>Andreas</ForeName>
<Initials>A</Initials>
</Author>
<Author ValidYN="Y"><LastName>Day</LastName>
<ForeName>Craig W</ForeName>
<Initials>CW</Initials>
</Author>
<Author ValidYN="Y"><LastName>Barnard</LastName>
<ForeName>Dale L</ForeName>
<Initials>DL</Initials>
</Author>
<Author ValidYN="Y"><LastName>Detorio</LastName>
<ForeName>Mervi A</ForeName>
<Initials>MA</Initials>
</Author>
<Author ValidYN="Y"><LastName>Schinazi</LastName>
<ForeName>Raymond F</ForeName>
<Initials>RF</Initials>
</Author>
</AuthorList>
<Language>eng</Language>
<GrantList CompleteYN="Y"><Grant><GrantID>2P30-AI-050409</GrantID>
<Acronym>AI</Acronym>
<Agency>NIAID NIH HHS</Agency>
<Country>United States</Country>
</Grant>
<Grant><GrantID>HHSN272201100019I/HHSN27200001/B01</GrantID>
<Agency>PHS HHS</Agency>
<Country>United States</Country>
</Grant>
<Grant><GrantID>HHSN272201100019I/HHSN27200002/B05</GrantID>
<Agency>PHS HHS</Agency>
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<ArticleDate DateType="Electronic"><Year>2012</Year>
<Month>12</Month>
<Day>07</Day>
</ArticleDate>
</Article>
<MedlineJournalInfo><Country>England</Country>
<MedlineTA>Antivir Chem Chemother</MedlineTA>
<NlmUniqueID>9009212</NlmUniqueID>
<ISSNLinking>0956-3202</ISSNLinking>
</MedlineJournalInfo>
<ChemicalList><Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D000998">Antiviral Agents</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D007097">Imines</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>2655-25-6</RegistryNumber>
<NameOfSubstance UI="C017621">phenylnitrene</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>BF4C9Z1J53</RegistryNumber>
<NameOfSubstance UI="D000547">Amantadine</NameOfSubstance>
</Chemical>
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<MeshHeadingList><MeshHeading><DescriptorName UI="D000547" MajorTopicYN="N">Amantadine</DescriptorName>
<QualifierName UI="Q000031" MajorTopicYN="N">analogs & derivatives</QualifierName>
<QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D000998" MajorTopicYN="N">Antiviral Agents</DescriptorName>
<QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName>
<QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D002478" MajorTopicYN="N">Cells, Cultured</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D018360" MajorTopicYN="N">Crystallography, X-Ray</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D015497" MajorTopicYN="N">HIV-1</DescriptorName>
<QualifierName UI="Q000187" MajorTopicYN="Y">drug effects</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D006801" MajorTopicYN="N">Humans</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D007097" MajorTopicYN="N">Imines</DescriptorName>
<QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName>
<QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName>
</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="D007251" MajorTopicYN="N">Influenza, Human</DescriptorName>
<QualifierName UI="Q000188" MajorTopicYN="N">drug therapy</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D008958" MajorTopicYN="N">Models, Molecular</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D010224" MajorTopicYN="N">Parainfluenza Virus 3, Human</DescriptorName>
<QualifierName UI="Q000187" MajorTopicYN="Y">drug effects</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D010253" MajorTopicYN="N">Respirovirus Infections</DescriptorName>
<QualifierName UI="Q000188" MajorTopicYN="N">drug therapy</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D045473" MajorTopicYN="N">SARS Virus</DescriptorName>
<QualifierName UI="Q000187" MajorTopicYN="Y">drug effects</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D045169" MajorTopicYN="N">Severe Acute Respiratory Syndrome</DescriptorName>
<QualifierName UI="Q000188" MajorTopicYN="N">drug therapy</QualifierName>
</MeshHeading>
</MeshHeadingList>
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<affiliations><list><country><li>Allemagne</li>
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<settlement><li>Munich</li>
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<tree><noCountry><name sortKey="Barnard, Dale L" sort="Barnard, Dale L" uniqKey="Barnard D" first="Dale L" last="Barnard">Dale L. Barnard</name>
<name sortKey="Day, Craig W" sort="Day, Craig W" uniqKey="Day C" first="Craig W" last="Day">Craig W. Day</name>
<name sortKey="Detorio, Mervi A" sort="Detorio, Mervi A" uniqKey="Detorio M" first="Mervi A" last="Detorio">Mervi A. Detorio</name>
<name sortKey="Schinazi, Raymond F" sort="Schinazi, Raymond F" uniqKey="Schinazi R" first="Raymond F" last="Schinazi">Raymond F. Schinazi</name>
<name sortKey="Schonleber, Andreas" sort="Schonleber, Andreas" uniqKey="Schonleber A" first="Andreas" last="Schönleber">Andreas Schönleber</name>
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<country name="Allemagne"><region name="Bavière"><name sortKey="Kesel, Andreas J" sort="Kesel, Andreas J" uniqKey="Kesel A" first="Andreas J" last="Kesel">Andreas J. Kesel</name>
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