Are the 2-isomers of the drug rimantadine active anti-influenza A agents?
Identifieur interne : 000337 ( PubMed/Corpus ); précédent : 000336; suivant : 000338Are the 2-isomers of the drug rimantadine active anti-influenza A agents?
Auteurs : Grigoris Zoidis ; Nicolas Kolocouris ; George B. Foscolos ; Antonios Kolocouris ; George Fytas ; P. Karayannis ; Elizaveta Padalko ; Johan Neyts ; Erik De ClercqSource :
- Antiviral chemistry & chemotherapy [ 0956-3202 ] ; 2003.
English descriptors
- KwdEn :
- Animals, Antiviral Agents (chemical synthesis), Antiviral Agents (pharmacology), Antiviral Agents (toxicity), Cells, Cultured (drug effects), Influenza A virus (drug effects), Influenza B virus (drug effects), Isomerism, Microbial Sensitivity Tests, Models, Chemical, Rimantadine (analogs & derivatives), Rimantadine (pharmacology), Rimantadine (toxicity), Structure-Activity Relationship.
- MESH :
- chemical , analogs & derivatives : Rimantadine.
- chemical , chemical synthesis : Antiviral Agents.
- chemical , pharmacology : Antiviral Agents, Rimantadine.
- chemical , toxicity : Antiviral Agents, Rimantadine.
- drug effects : Cells, Cultured, Influenza A virus, Influenza B virus.
- Animals, Isomerism, Microbial Sensitivity Tests, Models, Chemical, Structure-Activity Relationship.
Abstract
There is a lack of information in the medical chemistry literature concerning the anti-influenza A activity of the drug rimantadine's 2-isomer (2-rimantadine). We now present results showing that, although 2-adamantanamine (2-amantadine) 3 is only moderately active, some 2-rimantadine analogues are effective anti-influenza A virus agents in vitro. The 2-rimantadine analogues and their spirocyclobutane and spirocyclopentane congeners were synthesized through interesting routes. The 2-rimantadine analogues were 2-4 times more potent than rimantadine 2 against influenza virus A H2N2 strain; their spirocyclobutane congeners proved equally active to rimantadine 2. Two compounds exhibited a similar activity and one of the compounds was was fourfold more potent than rimantadine 2 against H3N2 strain.
DOI: 10.1177/095632020301400305
PubMed: 14521332
Links to Exploration step
pubmed:14521332Le document en format XML
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Foscolos</name></author><author><name sortKey="Kolocouris, Antonios" sort="Kolocouris, Antonios" uniqKey="Kolocouris A" first="Antonios" last="Kolocouris">Antonios Kolocouris</name></author><author><name sortKey="Fytas, George" sort="Fytas, George" uniqKey="Fytas G" first="George" last="Fytas">George Fytas</name></author><author><name sortKey="Karayannis, P" sort="Karayannis, P" uniqKey="Karayannis P" first="P" last="Karayannis">P. Karayannis</name></author><author><name sortKey="Padalko, Elizaveta" sort="Padalko, Elizaveta" uniqKey="Padalko E" first="Elizaveta" last="Padalko">Elizaveta Padalko</name></author><author><name sortKey="Neyts, Johan" sort="Neyts, Johan" uniqKey="Neyts J" first="Johan" last="Neyts">Johan Neyts</name></author><author><name sortKey="De Clercq, Erik" sort="De Clercq, Erik" uniqKey="De Clercq E" first="Erik" last="De Clercq">Erik De Clercq</name></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2003">2003</date><idno type="RBID">pubmed:14521332</idno><idno type="pmid">14521332</idno><idno type="doi">10.1177/095632020301400305</idno><idno type="wicri:Area/PubMed/Corpus">000337</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">000337</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Are the 2-isomers of the drug rimantadine active anti-influenza A agents?</title><author><name sortKey="Zoidis, Grigoris" sort="Zoidis, Grigoris" uniqKey="Zoidis G" first="Grigoris" last="Zoidis">Grigoris Zoidis</name><affiliation><nlm:affiliation>Department of Pharmacy, Division of Pharmaceutical Chemistry, University of Athens, Athens, Greece.</nlm:affiliation></affiliation></author><author><name sortKey="Kolocouris, Nicolas" sort="Kolocouris, Nicolas" uniqKey="Kolocouris N" first="Nicolas" last="Kolocouris">Nicolas Kolocouris</name></author><author><name sortKey="Foscolos, George B" sort="Foscolos, George B" uniqKey="Foscolos G" first="George B" last="Foscolos">George B. Foscolos</name></author><author><name sortKey="Kolocouris, Antonios" sort="Kolocouris, Antonios" uniqKey="Kolocouris A" first="Antonios" last="Kolocouris">Antonios Kolocouris</name></author><author><name sortKey="Fytas, George" sort="Fytas, George" uniqKey="Fytas G" first="George" last="Fytas">George Fytas</name></author><author><name sortKey="Karayannis, P" sort="Karayannis, P" uniqKey="Karayannis P" first="P" last="Karayannis">P. Karayannis</name></author><author><name sortKey="Padalko, Elizaveta" sort="Padalko, Elizaveta" uniqKey="Padalko E" first="Elizaveta" last="Padalko">Elizaveta Padalko</name></author><author><name sortKey="Neyts, Johan" sort="Neyts, Johan" uniqKey="Neyts J" first="Johan" last="Neyts">Johan Neyts</name></author><author><name sortKey="De Clercq, Erik" sort="De Clercq, Erik" uniqKey="De Clercq E" first="Erik" last="De Clercq">Erik De Clercq</name></author></analytic><series><title level="j">Antiviral chemistry & chemotherapy</title><idno type="ISSN">0956-3202</idno><imprint><date when="2003" type="published">2003</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Animals</term><term>Antiviral Agents (chemical synthesis)</term><term>Antiviral Agents (pharmacology)</term><term>Antiviral Agents (toxicity)</term><term>Cells, Cultured (drug effects)</term><term>Influenza A virus (drug effects)</term><term>Influenza B virus (drug effects)</term><term>Isomerism</term><term>Microbial Sensitivity Tests</term><term>Models, Chemical</term><term>Rimantadine (analogs & derivatives)</term><term>Rimantadine (pharmacology)</term><term>Rimantadine (toxicity)</term><term>Structure-Activity Relationship</term></keywords><keywords scheme="MESH" type="chemical" qualifier="analogs & derivatives" xml:lang="en"><term>Rimantadine</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Antiviral Agents</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Antiviral Agents</term><term>Rimantadine</term></keywords><keywords scheme="MESH" type="chemical" qualifier="toxicity" xml:lang="en"><term>Antiviral Agents</term><term>Rimantadine</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Cells, Cultured</term><term>Influenza A virus</term><term>Influenza B virus</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Animals</term><term>Isomerism</term><term>Microbial Sensitivity Tests</term><term>Models, Chemical</term><term>Structure-Activity Relationship</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">There is a lack of information in the medical chemistry literature concerning the anti-influenza A activity of the drug rimantadine's 2-isomer (2-rimantadine). We now present results showing that, although 2-adamantanamine (2-amantadine) 3 is only moderately active, some 2-rimantadine analogues are effective anti-influenza A virus agents in vitro. The 2-rimantadine analogues and their spirocyclobutane and spirocyclopentane congeners were synthesized through interesting routes. The 2-rimantadine analogues were 2-4 times more potent than rimantadine 2 against influenza virus A H2N2 strain; their spirocyclobutane congeners proved equally active to rimantadine 2. Two compounds exhibited a similar activity and one of the compounds was was fourfold more potent than rimantadine 2 against H3N2 strain.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">14521332</PMID><DateCompleted><Year>2004</Year><Month>04</Month><Day>20</Day></DateCompleted><DateRevised><Year>2017</Year><Month>02</Month><Day>14</Day></DateRevised><Article PubModel="Print"><Journal><ISSN IssnType="Print">0956-3202</ISSN><JournalIssue CitedMedium="Print"><Volume>14</Volume><Issue>3</Issue><PubDate><Year>2003</Year><Month>May</Month></PubDate></JournalIssue><Title>Antiviral chemistry & chemotherapy</Title><ISOAbbreviation>Antivir. Chem. Chemother.</ISOAbbreviation></Journal><ArticleTitle>Are the 2-isomers of the drug rimantadine active anti-influenza A agents?</ArticleTitle><Pagination><MedlinePgn>153-64</MedlinePgn></Pagination><Abstract><AbstractText>There is a lack of information in the medical chemistry literature concerning the anti-influenza A activity of the drug rimantadine's 2-isomer (2-rimantadine). We now present results showing that, although 2-adamantanamine (2-amantadine) 3 is only moderately active, some 2-rimantadine analogues are effective anti-influenza A virus agents in vitro. The 2-rimantadine analogues and their spirocyclobutane and spirocyclopentane congeners were synthesized through interesting routes. The 2-rimantadine analogues were 2-4 times more potent than rimantadine 2 against influenza virus A H2N2 strain; their spirocyclobutane congeners proved equally active to rimantadine 2. Two compounds exhibited a similar activity and one of the compounds was was fourfold more potent than rimantadine 2 against H3N2 strain.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Zoidis</LastName><ForeName>Grigoris</ForeName><Initials>G</Initials><AffiliationInfo><Affiliation>Department of Pharmacy, Division of Pharmaceutical Chemistry, University of Athens, Athens, Greece.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Kolocouris</LastName><ForeName>Nicolas</ForeName><Initials>N</Initials></Author><Author ValidYN="Y"><LastName>Foscolos</LastName><ForeName>George B</ForeName><Initials>GB</Initials></Author><Author ValidYN="Y"><LastName>Kolocouris</LastName><ForeName>Antonios</ForeName><Initials>A</Initials></Author><Author ValidYN="Y"><LastName>Fytas</LastName><ForeName>George</ForeName><Initials>G</Initials></Author><Author ValidYN="Y"><LastName>Karayannis</LastName><ForeName>P</ForeName><Initials>P</Initials></Author><Author ValidYN="Y"><LastName>Padalko</LastName><ForeName>Elizaveta</ForeName><Initials>E</Initials></Author><Author ValidYN="Y"><LastName>Neyts</LastName><ForeName>Johan</ForeName><Initials>J</Initials></Author><Author ValidYN="Y"><LastName>De Clercq</LastName><ForeName>Erik</ForeName><Initials>E</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>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>0T2EF4JQTU</RegistryNumber><NameOfSubstance UI="D012299">Rimantadine</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D000818" MajorTopicYN="N">Animals</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D000998" MajorTopicYN="N">Antiviral Agents</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="Y">chemical synthesis</QualifierName><QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName><QualifierName UI="Q000633" MajorTopicYN="N">toxicity</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D002478" MajorTopicYN="N">Cells, Cultured</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="N">drug effects</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="N">drug effects</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D007536" MajorTopicYN="N">Isomerism</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D008826" MajorTopicYN="N">Microbial Sensitivity Tests</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D008956" MajorTopicYN="N">Models, Chemical</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D012299" MajorTopicYN="N">Rimantadine</DescriptorName><QualifierName UI="Q000031" MajorTopicYN="Y">analogs & derivatives</QualifierName><QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName><QualifierName UI="Q000633" MajorTopicYN="N">toxicity</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D013329" MajorTopicYN="N">Structure-Activity Relationship</DescriptorName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="pubmed"><Year>2003</Year><Month>10</Month><Day>3</Day><Hour>5</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2004</Year><Month>4</Month><Day>21</Day><Hour>5</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2003</Year><Month>10</Month><Day>3</Day><Hour>5</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">14521332</ArticleId><ArticleId IdType="doi">10.1177/095632020301400305</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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