The application of phosphoramidate ProTide technology to the potent anti-HCV compound 4'-azidocytidine (R1479).
Identifieur interne : 001F37 ( Ncbi/Merge ); précédent : 001F36; suivant : 001F38The application of phosphoramidate ProTide technology to the potent anti-HCV compound 4'-azidocytidine (R1479).
Auteurs : Christopher Mcguigan [Royaume-Uni] ; Mary Rose Kelleher ; Plinio Perrone ; Sinead Mulready ; Giovanna Luoni ; Felice Daverio ; Sonal Rajyaguru ; Sophie Le Pogam ; Isabel Najera ; Joseph A. Martin ; Klaus Klumpp ; David B. SmithSource :
- Bioorganic & medicinal chemistry letters [ 1464-3405 ] ; 2009.
Descripteurs français
- KwdFr :
- Acides aminés (), Antiviraux (pharmacologie), Antiviraux (synthèse chimique), Chimie pharmaceutique (), Conception de médicament, Cytidine (analogues et dérivés), Cytidine (pharmacologie), Cytidine (synthèse chimique), Hepacivirus (métabolisme), Humains, Hépatite C (traitement médicamenteux), Modèles chimiques, Promédicaments, Réplication virale, Réplicon (), Technologie pharmaceutique (), Évaluation préclinique de médicament.
- MESH :
- analogues et dérivés : Cytidine.
- métabolisme : Hepacivirus.
- pharmacologie : Antiviraux, Cytidine.
- synthèse chimique : Antiviraux, Cytidine.
- traitement médicamenteux : Hépatite C.
- Acides aminés, Chimie pharmaceutique, Conception de médicament, Humains, Modèles chimiques, Promédicaments, Réplication virale, Réplicon, Technologie pharmaceutique, Évaluation préclinique de médicament.
English descriptors
- KwdEn :
- Amino Acids (chemistry), Antiviral Agents (chemical synthesis), Antiviral Agents (pharmacology), Chemistry, Pharmaceutical (methods), Cytidine (analogs & derivatives), Cytidine (chemical synthesis), Cytidine (pharmacology), Drug Design, Drug Evaluation, Preclinical, Hepacivirus (metabolism), Hepatitis C (drug therapy), Humans, Models, Chemical, Prodrugs, Replicon (drug effects), Technology, Pharmaceutical (methods), Virus Replication.
- MESH :
- chemical , analogs & derivatives : Cytidine.
- chemical , chemical synthesis : Antiviral Agents, Cytidine.
- chemical , chemistry : Amino Acids.
- chemical , pharmacology : Antiviral Agents, Cytidine.
- drug effects : Replicon.
- drug therapy : Hepatitis C.
- metabolism : Hepacivirus.
- methods : Chemistry, Pharmaceutical, Technology, Pharmaceutical.
- Drug Design, Drug Evaluation, Preclinical, Humans, Models, Chemical, Prodrugs, Virus Replication.
Abstract
We report the design, synthesis and evaluation of a family of ca 50 phosphoramidate ProTides of the potent anti-HCV compound 4'-azidocytidine (R1479), with variation on the ester, amino acid and aryl moiety of the ProTide. Sub-muM inhibitors of HCV emerge. The compounds are all non-cytotoxic in the replicon assay. We herein report detailed SARs for each of the regions of the ProTide.
DOI: 10.1016/j.bmcl.2009.05.099
PubMed: 19505826
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pubmed:19505826Le document en format XML
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Sub-muM inhibitors of HCV emerge. The compounds are all non-cytotoxic in the replicon assay. We herein report detailed SARs for each of the regions of the ProTide.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">19505826</PMID><DateCompleted><Year>2009</Year><Month>12</Month><Day>07</Day></DateCompleted><DateRevised><Year>2019</Year><Month>01</Month><Day>07</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1464-3405</ISSN><JournalIssue CitedMedium="Internet"><Volume>19</Volume><Issue>15</Issue><PubDate><Year>2009</Year><Month>Aug</Month><Day>01</Day></PubDate></JournalIssue><Title>Bioorganic & medicinal chemistry letters</Title><ISOAbbreviation>Bioorg. Med. Chem. Lett.</ISOAbbreviation></Journal><ArticleTitle>The application of phosphoramidate ProTide technology to the potent anti-HCV compound 4'-azidocytidine (R1479).</ArticleTitle><Pagination><MedlinePgn>4250-4</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1016/j.bmcl.2009.05.099</ELocationID><Abstract><AbstractText>We report the design, synthesis and evaluation of a family of ca 50 phosphoramidate ProTides of the potent anti-HCV compound 4'-azidocytidine (R1479), with variation on the ester, amino acid and aryl moiety of the ProTide. Sub-muM inhibitors of HCV emerge. The compounds are all non-cytotoxic in the replicon assay. We herein report detailed SARs for each of the regions of the ProTide.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>McGuigan</LastName><ForeName>Christopher</ForeName><Initials>C</Initials><AffiliationInfo><Affiliation>Welsh School of Pharmacy, Cardiff University, Redwood Building, King Edward VII Avenue, Cardiff CF10 3NB, UK. mcguigan@cardiff.ac.uk</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Kelleher</LastName><ForeName>Mary Rose</ForeName><Initials>MR</Initials></Author><Author ValidYN="Y"><LastName>Perrone</LastName><ForeName>Plinio</ForeName><Initials>P</Initials></Author><Author ValidYN="Y"><LastName>Mulready</LastName><ForeName>Sinead</ForeName><Initials>S</Initials></Author><Author ValidYN="Y"><LastName>Luoni</LastName><ForeName>Giovanna</ForeName><Initials>G</Initials></Author><Author ValidYN="Y"><LastName>Daverio</LastName><ForeName>Felice</ForeName><Initials>F</Initials></Author><Author ValidYN="Y"><LastName>Rajyaguru</LastName><ForeName>Sonal</ForeName><Initials>S</Initials></Author><Author ValidYN="Y"><LastName>Le Pogam</LastName><ForeName>Sophie</ForeName><Initials>S</Initials></Author><Author ValidYN="Y"><LastName>Najera</LastName><ForeName>Isabel</ForeName><Initials>I</Initials></Author><Author ValidYN="Y"><LastName>Martin</LastName><ForeName>Joseph A</ForeName><Initials>JA</Initials></Author><Author ValidYN="Y"><LastName>Klumpp</LastName><ForeName>Klaus</ForeName><Initials>K</Initials></Author><Author ValidYN="Y"><LastName>Smith</LastName><ForeName>David B</ForeName><Initials>DB</Initials></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2009</Year><Month>05</Month><Day>29</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="D000596">Amino Acids</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000998">Antiviral Agents</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D011355">Prodrugs</NameOfSubstance></Chemical><Chemical><RegistryNumber>5CSZ8459RP</RegistryNumber><NameOfSubstance UI="D003562">Cytidine</NameOfSubstance></Chemical><Chemical><RegistryNumber>M71RA9DMGJ</RegistryNumber><NameOfSubstance UI="C508950">4'-azidocytidine</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D000596" MajorTopicYN="N">Amino Acids</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></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></MeshHeading><MeshHeading><DescriptorName UI="D002626" MajorTopicYN="N">Chemistry, Pharmaceutical</DescriptorName><QualifierName UI="Q000379" MajorTopicYN="Y">methods</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D003562" MajorTopicYN="N">Cytidine</DescriptorName><QualifierName UI="Q000031" MajorTopicYN="Y">analogs & derivatives</QualifierName><QualifierName UI="Q000138" MajorTopicYN="N">chemical synthesis</QualifierName><QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D015195" MajorTopicYN="N">Drug Design</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D004353" MajorTopicYN="N">Drug Evaluation, Preclinical</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D016174" MajorTopicYN="N">Hepacivirus</DescriptorName><QualifierName UI="Q000378" MajorTopicYN="Y">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D006526" MajorTopicYN="N">Hepatitis C</DescriptorName><QualifierName UI="Q000188" MajorTopicYN="Y">drug therapy</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D006801" MajorTopicYN="N">Humans</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D008956" MajorTopicYN="N">Models, Chemical</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D011355" MajorTopicYN="N">Prodrugs</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D012093" MajorTopicYN="N">Replicon</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D013678" MajorTopicYN="N">Technology, Pharmaceutical</DescriptorName><QualifierName UI="Q000379" MajorTopicYN="Y">methods</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D014779" MajorTopicYN="N">Virus Replication</DescriptorName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2009</Year><Month>04</Month><Day>15</Day></PubMedPubDate><PubMedPubDate PubStatus="revised"><Year>2009</Year><Month>05</Month><Day>21</Day></PubMedPubDate><PubMedPubDate PubStatus="accepted"><Year>2009</Year><Month>05</Month><Day>22</Day></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2009</Year><Month>6</Month><Day>10</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2009</Year><Month>6</Month><Day>10</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2009</Year><Month>12</Month><Day>16</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">19505826</ArticleId><ArticleId IdType="pii">S0960-894X(09)00790-2</ArticleId><ArticleId IdType="doi">10.1016/j.bmcl.2009.05.099</ArticleId></ArticleIdList></PubmedData></pubmed><affiliations><list><country><li>Royaume-Uni</li></country></list><tree><noCountry><name sortKey="Daverio, Felice" sort="Daverio, Felice" uniqKey="Daverio F" first="Felice" last="Daverio">Felice Daverio</name><name sortKey="Kelleher, Mary Rose" sort="Kelleher, Mary Rose" uniqKey="Kelleher M" first="Mary Rose" last="Kelleher">Mary Rose Kelleher</name><name sortKey="Klumpp, Klaus" sort="Klumpp, Klaus" uniqKey="Klumpp K" first="Klaus" last="Klumpp">Klaus Klumpp</name><name sortKey="Le Pogam, Sophie" sort="Le Pogam, Sophie" uniqKey="Le Pogam S" first="Sophie" last="Le Pogam">Sophie Le Pogam</name><name sortKey="Luoni, Giovanna" sort="Luoni, Giovanna" uniqKey="Luoni G" first="Giovanna" last="Luoni">Giovanna Luoni</name><name sortKey="Martin, Joseph A" sort="Martin, Joseph A" uniqKey="Martin J" first="Joseph A" last="Martin">Joseph A. Martin</name><name sortKey="Mulready, Sinead" sort="Mulready, Sinead" uniqKey="Mulready S" first="Sinead" last="Mulready">Sinead Mulready</name><name sortKey="Najera, Isabel" sort="Najera, Isabel" uniqKey="Najera I" first="Isabel" last="Najera">Isabel Najera</name><name sortKey="Perrone, Plinio" sort="Perrone, Plinio" uniqKey="Perrone P" first="Plinio" last="Perrone">Plinio Perrone</name><name sortKey="Rajyaguru, Sonal" sort="Rajyaguru, Sonal" uniqKey="Rajyaguru S" first="Sonal" last="Rajyaguru">Sonal Rajyaguru</name><name sortKey="Smith, David B" sort="Smith, David B" uniqKey="Smith D" first="David B" last="Smith">David B. Smith</name></noCountry><country name="Royaume-Uni"><noRegion><name sortKey="Mcguigan, Christopher" sort="Mcguigan, Christopher" uniqKey="Mcguigan C" first="Christopher" last="Mcguigan">Christopher Mcguigan</name></noRegion></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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