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:
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Kesel</name><affiliation wicri:level="3"><nlm:affiliation>Chammünsterstr 47, Munich, Germany. andreas.kesel@gmx.de.</nlm:affiliation><country xml:lang="fr">Allemagne</country><wicri:regionArea>Chammünsterstr 47, Munich</wicri:regionArea><placeName><region type="land" nuts="1">Bavière</region><region type="district" nuts="2">District de Haute-Bavière</region><settlement type="city">Munich</settlement></placeName></affiliation></author><author><name sortKey="Weiss, Hans Christoph" sort="Weiss, Hans Christoph" uniqKey="Weiss H" first="Hans-Christoph" last="Weiss">Hans-Christoph Weiss</name></author><author><name sortKey="Schonleber, Andreas" sort="Schonleber, Andreas" uniqKey="Schonleber A" first="Andreas" last="Schönleber">Andreas Schönleber</name></author><author><name sortKey="Day, Craig W" sort="Day, Craig W" uniqKey="Day C" first="Craig W" last="Day">Craig W. 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Kesel</name><affiliation wicri:level="3"><nlm:affiliation>Chammünsterstr 47, Munich, Germany. andreas.kesel@gmx.de.</nlm:affiliation><country xml:lang="fr">Allemagne</country><wicri:regionArea>Chammünsterstr 47, Munich</wicri:regionArea><placeName><region type="land" nuts="1">Bavière</region><region type="district" nuts="2">District de Haute-Bavière</region><settlement type="city">Munich</settlement></placeName></affiliation></author><author><name sortKey="Weiss, Hans Christoph" sort="Weiss, Hans Christoph" uniqKey="Weiss H" first="Hans-Christoph" last="Weiss">Hans-Christoph Weiss</name></author><author><name sortKey="Schonleber, Andreas" sort="Schonleber, Andreas" uniqKey="Schonleber A" first="Andreas" last="Schönleber">Andreas Schönleber</name></author><author><name sortKey="Day, Craig W" sort="Day, Craig W" uniqKey="Day C" first="Craig W" last="Day">Craig W. Day</name></author><author><name sortKey="Barnard, Dale L" sort="Barnard, Dale L" uniqKey="Barnard D" first="Dale L" last="Barnard">Dale L. Barnard</name></author><author><name sortKey="Detorio, Mervi A" sort="Detorio, Mervi A" uniqKey="Detorio M" first="Mervi A" last="Detorio">Mervi A. Detorio</name></author><author><name sortKey="Schinazi, Raymond F" sort="Schinazi, Raymond F" uniqKey="Schinazi R" first="Raymond F" last="Schinazi">Raymond F. Schinazi</name></author></analytic><series><title level="j">Antiviral chemistry & chemotherapy</title><idno type="eISSN">2040-2066</idno><imprint><date when="2012" type="published">2012</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Amantadine (analogs & derivatives)</term><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></keywords><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></keywords><keywords scheme="MESH" type="chemical" qualifier="analogs & derivatives" xml:lang="en"><term>Amantadine</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Antiviral Agents</term><term>Imines</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Amantadine</term><term>Antiviral Agents</term><term>Imines</term></keywords><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><keywords scheme="MESH" qualifier="drug therapy" xml:lang="en"><term>Influenza, Human</term><term>Respirovirus Infections</term><term>Severe Acute Respiratory Syndrome</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Amantadine</term><term>Antiviraux</term><term>Imines</term></keywords><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><keywords scheme="MESH" xml:lang="fr"><term>Antiviraux</term><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><term>Virus du SRAS</term><term>Virus influenza B</term><term>Virus parainfluenza humain de type 3</term></keywords></textClass></profileDesc></teiHeader><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><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="D013486">Research Support, U.S. Gov't, Non-P.H.S.</PublicationType></PublicationTypeList><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></ChemicalList><CitationSubset>IM</CitationSubset><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></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="accepted"><Year>2012</Year><Month>11</Month><Day>21</Day></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2012</Year><Month>12</Month><Day>14</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2012</Year><Month>12</Month><Day>14</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2014</Year><Month>7</Month><Day>10</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>epublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">23234699</ArticleId><ArticleId IdType="doi">10.3851/IMP2485</ArticleId></ArticleIdList></PubmedData></pubmed><affiliations><list><country><li>Allemagne</li></country><region><li>Bavière</li><li>District de Haute-Bavière</li></region><settlement><li>Munich</li></settlement></list><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><name sortKey="Weiss, Hans Christoph" sort="Weiss, Hans Christoph" uniqKey="Weiss H" first="Hans-Christoph" last="Weiss">Hans-Christoph Weiss</name></noCountry><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></region></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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