Synthesis and biological evaluation of 2-oxonicotinonitriles and 2-oxonicotinonitrile based nucleoside analogues.
Identifieur interne : 001056 ( PubMed/Curation ); précédent : 001055; suivant : 001057Synthesis and biological evaluation of 2-oxonicotinonitriles and 2-oxonicotinonitrile based nucleoside analogues.
Auteurs : Reham A I. Abou-Elkhair [Égypte] ; Ahmed H. Moustafa [Égypte] ; Abdelfattah Z. Haikal [Égypte] ; Ahmed M. Ibraheem [Égypte]Source :
- European journal of medicinal chemistry [ 1768-3254 ] ; 2014.
Descripteurs français
- KwdFr :
- MESH :
- pharmacologie : Nitriles.
- synthèse chimique : Nitriles.
- Bactéries, Tests de sensibilité microbienne, Virus.
English descriptors
- KwdEn :
- MESH :
- chemical , chemical synthesis : Nitriles.
- drug effects : Bacteria, Viruses.
- chemical , pharmacology : Nitriles.
- Microbial Sensitivity Tests.
Abstract
Drug resistance and emergence of new pathogens highlight the need for developing new therapeutic agents. We focused on 2-oxonicotinonitrile (2-ONN) as derivative of the natural product 2-pyridinone.(1) Herein, we describe the synthesis of 2-ONNs bearing two aryl groups, which we coupled with organohalides, including three glycosyl bromides, to prepare the nucleoside analogues. Coupling occurred mostly at the 2-ONN ring nitrogen to give the aimed targets, and in a few cases, it happened at the 2-oxo position giving O-alkylation products. Free 2-ONNs and their acetylated nucleosides were tested against a number of viruses. The nucleoside analogue 2a(Ac) showed good anti SARS-CoV and anti influenza A (H₅N₁) activities. Additionally, 7b had good activity against Gram positive bacterium, Bacillis subtilis.
DOI: 10.1016/j.ejmech.2013.12.055
PubMed: 24486419
Links toward previous steps (curation, corpus...)
- to stream PubMed, to step Corpus: Pour aller vers cette notice dans l'étape Curation :001056
Links to Exploration step
pubmed:24486419Le document en format XML
<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Synthesis and biological evaluation of 2-oxonicotinonitriles and 2-oxonicotinonitrile based nucleoside analogues.</title>
<author><name sortKey="Abou Elkhair, Reham A I" sort="Abou Elkhair, Reham A I" uniqKey="Abou Elkhair R" first="Reham A I" last="Abou-Elkhair">Reham A I. Abou-Elkhair</name>
<affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry, Faculty of Sciences, Zagazig University, Zagazig, Egypt. Electronic address: rabouelkhair@zu.edu.eg.</nlm:affiliation>
<country xml:lang="fr">Égypte</country>
<wicri:regionArea>Department of Chemistry, Faculty of Sciences, Zagazig University, Zagazig</wicri:regionArea>
</affiliation>
</author>
<author><name sortKey="Moustafa, Ahmed H" sort="Moustafa, Ahmed H" uniqKey="Moustafa A" first="Ahmed H" last="Moustafa">Ahmed H. Moustafa</name>
<affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry, Faculty of Sciences, Zagazig University, Zagazig, Egypt. Electronic address: ah_hu_mostafa@yahoo.com.</nlm:affiliation>
<country xml:lang="fr">Égypte</country>
<wicri:regionArea>Department of Chemistry, Faculty of Sciences, Zagazig University, Zagazig</wicri:regionArea>
</affiliation>
</author>
<author><name sortKey="Haikal, Abdelfattah Z" sort="Haikal, Abdelfattah Z" uniqKey="Haikal A" first="Abdelfattah Z" last="Haikal">Abdelfattah Z. Haikal</name>
<affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry, Faculty of Sciences, Zagazig University, Zagazig, Egypt.</nlm:affiliation>
<country xml:lang="fr">Égypte</country>
<wicri:regionArea>Department of Chemistry, Faculty of Sciences, Zagazig University, Zagazig</wicri:regionArea>
</affiliation>
</author>
<author><name sortKey="Ibraheem, Ahmed M" sort="Ibraheem, Ahmed M" uniqKey="Ibraheem A" first="Ahmed M" last="Ibraheem">Ahmed M. Ibraheem</name>
<affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry, Faculty of Sciences, Zagazig University, Zagazig, Egypt.</nlm:affiliation>
<country xml:lang="fr">Égypte</country>
<wicri:regionArea>Department of Chemistry, Faculty of Sciences, Zagazig University, Zagazig</wicri:regionArea>
</affiliation>
</author>
</titleStmt>
<publicationStmt><idno type="wicri:source">PubMed</idno>
<date when="2014">2014</date>
<idno type="RBID">pubmed:24486419</idno>
<idno type="pmid">24486419</idno>
<idno type="doi">10.1016/j.ejmech.2013.12.055</idno>
<idno type="wicri:Area/PubMed/Corpus">001056</idno>
<idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">001056</idno>
<idno type="wicri:Area/PubMed/Curation">001056</idno>
<idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Curation">001056</idno>
</publicationStmt>
<sourceDesc><biblStruct><analytic><title xml:lang="en">Synthesis and biological evaluation of 2-oxonicotinonitriles and 2-oxonicotinonitrile based nucleoside analogues.</title>
<author><name sortKey="Abou Elkhair, Reham A I" sort="Abou Elkhair, Reham A I" uniqKey="Abou Elkhair R" first="Reham A I" last="Abou-Elkhair">Reham A I. Abou-Elkhair</name>
<affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry, Faculty of Sciences, Zagazig University, Zagazig, Egypt. Electronic address: rabouelkhair@zu.edu.eg.</nlm:affiliation>
<country xml:lang="fr">Égypte</country>
<wicri:regionArea>Department of Chemistry, Faculty of Sciences, Zagazig University, Zagazig</wicri:regionArea>
</affiliation>
</author>
<author><name sortKey="Moustafa, Ahmed H" sort="Moustafa, Ahmed H" uniqKey="Moustafa A" first="Ahmed H" last="Moustafa">Ahmed H. Moustafa</name>
<affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry, Faculty of Sciences, Zagazig University, Zagazig, Egypt. Electronic address: ah_hu_mostafa@yahoo.com.</nlm:affiliation>
<country xml:lang="fr">Égypte</country>
<wicri:regionArea>Department of Chemistry, Faculty of Sciences, Zagazig University, Zagazig</wicri:regionArea>
</affiliation>
</author>
<author><name sortKey="Haikal, Abdelfattah Z" sort="Haikal, Abdelfattah Z" uniqKey="Haikal A" first="Abdelfattah Z" last="Haikal">Abdelfattah Z. Haikal</name>
<affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry, Faculty of Sciences, Zagazig University, Zagazig, Egypt.</nlm:affiliation>
<country xml:lang="fr">Égypte</country>
<wicri:regionArea>Department of Chemistry, Faculty of Sciences, Zagazig University, Zagazig</wicri:regionArea>
</affiliation>
</author>
<author><name sortKey="Ibraheem, Ahmed M" sort="Ibraheem, Ahmed M" uniqKey="Ibraheem A" first="Ahmed M" last="Ibraheem">Ahmed M. Ibraheem</name>
<affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry, Faculty of Sciences, Zagazig University, Zagazig, Egypt.</nlm:affiliation>
<country xml:lang="fr">Égypte</country>
<wicri:regionArea>Department of Chemistry, Faculty of Sciences, Zagazig University, Zagazig</wicri:regionArea>
</affiliation>
</author>
</analytic>
<series><title level="j">European journal of medicinal chemistry</title>
<idno type="eISSN">1768-3254</idno>
<imprint><date when="2014" type="published">2014</date>
</imprint>
</series>
</biblStruct>
</sourceDesc>
</fileDesc>
<profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Bacteria (drug effects)</term>
<term>Microbial Sensitivity Tests</term>
<term>Nitriles (chemical synthesis)</term>
<term>Nitriles (pharmacology)</term>
<term>Viruses (drug effects)</term>
</keywords>
<keywords scheme="KwdFr" xml:lang="fr"><term>Bactéries ()</term>
<term>Nitriles (pharmacologie)</term>
<term>Nitriles (synthèse chimique)</term>
<term>Tests de sensibilité microbienne</term>
<term>Virus ()</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Nitriles</term>
</keywords>
<keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Bacteria</term>
<term>Viruses</term>
</keywords>
<keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Nitriles</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Nitriles</term>
</keywords>
<keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Nitriles</term>
</keywords>
<keywords scheme="MESH" xml:lang="en"><term>Microbial Sensitivity Tests</term>
</keywords>
<keywords scheme="MESH" xml:lang="fr"><term>Bactéries</term>
<term>Tests de sensibilité microbienne</term>
<term>Virus</term>
</keywords>
</textClass>
</profileDesc>
</teiHeader>
<front><div type="abstract" xml:lang="en">Drug resistance and emergence of new pathogens highlight the need for developing new therapeutic agents. We focused on 2-oxonicotinonitrile (2-ONN) as derivative of the natural product 2-pyridinone.(1) Herein, we describe the synthesis of 2-ONNs bearing two aryl groups, which we coupled with organohalides, including three glycosyl bromides, to prepare the nucleoside analogues. Coupling occurred mostly at the 2-ONN ring nitrogen to give the aimed targets, and in a few cases, it happened at the 2-oxo position giving O-alkylation products. Free 2-ONNs and their acetylated nucleosides were tested against a number of viruses. The nucleoside analogue 2a(Ac) showed good anti SARS-CoV and anti influenza A (H₅N₁) activities. Additionally, 7b had good activity against Gram positive bacterium, Bacillis subtilis.</div>
</front>
</TEI>
<pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">24486419</PMID>
<DateCompleted><Year>2014</Year>
<Month>11</Month>
<Day>04</Day>
</DateCompleted>
<DateRevised><Year>2020</Year>
<Month>04</Month>
<Day>07</Day>
</DateRevised>
<Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1768-3254</ISSN>
<JournalIssue CitedMedium="Internet"><Volume>74</Volume>
<PubDate><Year>2014</Year>
<Month>Mar</Month>
<Day>03</Day>
</PubDate>
</JournalIssue>
<Title>European journal of medicinal chemistry</Title>
<ISOAbbreviation>Eur J Med Chem</ISOAbbreviation>
</Journal>
<ArticleTitle>Synthesis and biological evaluation of 2-oxonicotinonitriles and 2-oxonicotinonitrile based nucleoside analogues.</ArticleTitle>
<Pagination><MedlinePgn>388-97</MedlinePgn>
</Pagination>
<ELocationID EIdType="doi" ValidYN="Y">10.1016/j.ejmech.2013.12.055</ELocationID>
<ELocationID EIdType="pii" ValidYN="Y">S0223-5234(14)00017-8</ELocationID>
<Abstract><AbstractText>Drug resistance and emergence of new pathogens highlight the need for developing new therapeutic agents. We focused on 2-oxonicotinonitrile (2-ONN) as derivative of the natural product 2-pyridinone.(1) Herein, we describe the synthesis of 2-ONNs bearing two aryl groups, which we coupled with organohalides, including three glycosyl bromides, to prepare the nucleoside analogues. Coupling occurred mostly at the 2-ONN ring nitrogen to give the aimed targets, and in a few cases, it happened at the 2-oxo position giving O-alkylation products. Free 2-ONNs and their acetylated nucleosides were tested against a number of viruses. The nucleoside analogue 2a(Ac) showed good anti SARS-CoV and anti influenza A (H₅N₁) activities. Additionally, 7b had good activity against Gram positive bacterium, Bacillis subtilis.</AbstractText>
<CopyrightInformation>Copyright © 2014 Elsevier Masson SAS. All rights reserved.</CopyrightInformation>
</Abstract>
<AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Abou-Elkhair</LastName>
<ForeName>Reham A I</ForeName>
<Initials>RA</Initials>
<AffiliationInfo><Affiliation>Department of Chemistry, Faculty of Sciences, Zagazig University, Zagazig, Egypt. Electronic address: rabouelkhair@zu.edu.eg.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Moustafa</LastName>
<ForeName>Ahmed H</ForeName>
<Initials>AH</Initials>
<AffiliationInfo><Affiliation>Department of Chemistry, Faculty of Sciences, Zagazig University, Zagazig, Egypt. Electronic address: ah_hu_mostafa@yahoo.com.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Haikal</LastName>
<ForeName>Abdelfattah Z</ForeName>
<Initials>AZ</Initials>
<AffiliationInfo><Affiliation>Department of Chemistry, Faculty of Sciences, Zagazig University, Zagazig, Egypt.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Ibraheem</LastName>
<ForeName>Ahmed M</ForeName>
<Initials>AM</Initials>
<AffiliationInfo><Affiliation>Department of Chemistry, Faculty of Sciences, Zagazig University, Zagazig, Egypt.</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>2014</Year>
<Month>01</Month>
<Day>08</Day>
</ArticleDate>
</Article>
<MedlineJournalInfo><Country>France</Country>
<MedlineTA>Eur J Med Chem</MedlineTA>
<NlmUniqueID>0420510</NlmUniqueID>
<ISSNLinking>0223-5234</ISSNLinking>
</MedlineJournalInfo>
<ChemicalList><Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D009570">Nitriles</NameOfSubstance>
</Chemical>
</ChemicalList>
<CitationSubset>IM</CitationSubset>
<MeshHeadingList><MeshHeading><DescriptorName UI="D001419" MajorTopicYN="N">Bacteria</DescriptorName>
<QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D008826" MajorTopicYN="N">Microbial Sensitivity Tests</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D009570" MajorTopicYN="N">Nitriles</DescriptorName>
<QualifierName UI="Q000138" MajorTopicYN="Y">chemical synthesis</QualifierName>
<QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D014780" MajorTopicYN="N">Viruses</DescriptorName>
<QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName>
</MeshHeading>
</MeshHeadingList>
<KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">2-Oxonicotinonitrile</Keyword>
<Keyword MajorTopicYN="N">2-Pyridinone</Keyword>
<Keyword MajorTopicYN="N">Antimicrobial</Keyword>
<Keyword MajorTopicYN="N">Antiviral</Keyword>
<Keyword MajorTopicYN="N">Glycosylation</Keyword>
<Keyword MajorTopicYN="N">Nucleoside analogues</Keyword>
</KeywordList>
</MedlineCitation>
<PubmedData><History><PubMedPubDate PubStatus="received"><Year>2013</Year>
<Month>11</Month>
<Day>08</Day>
</PubMedPubDate>
<PubMedPubDate PubStatus="revised"><Year>2013</Year>
<Month>12</Month>
<Day>25</Day>
</PubMedPubDate>
<PubMedPubDate PubStatus="accepted"><Year>2013</Year>
<Month>12</Month>
<Day>26</Day>
</PubMedPubDate>
<PubMedPubDate PubStatus="entrez"><Year>2014</Year>
<Month>2</Month>
<Day>4</Day>
<Hour>6</Hour>
<Minute>0</Minute>
</PubMedPubDate>
<PubMedPubDate PubStatus="pubmed"><Year>2014</Year>
<Month>2</Month>
<Day>4</Day>
<Hour>6</Hour>
<Minute>0</Minute>
</PubMedPubDate>
<PubMedPubDate PubStatus="medline"><Year>2014</Year>
<Month>11</Month>
<Day>5</Day>
<Hour>6</Hour>
<Minute>0</Minute>
</PubMedPubDate>
</History>
<PublicationStatus>ppublish</PublicationStatus>
<ArticleIdList><ArticleId IdType="pubmed">24486419</ArticleId>
<ArticleId IdType="pii">S0223-5234(14)00017-8</ArticleId>
<ArticleId IdType="doi">10.1016/j.ejmech.2013.12.055</ArticleId>
<ArticleId IdType="pmc">PMC7115408</ArticleId>
</ArticleIdList>
<ReferenceList><Reference><Citation>Eur J Med Chem. 2011 Jul;46(7):2948-54</Citation>
<ArticleIdList><ArticleId IdType="pubmed">21531049</ArticleId>
</ArticleIdList>
</Reference>
</ReferenceList>
<ReferenceList><Reference><Citation>Nat Prod Rep. 2010 Aug;27(8):1168-85</Citation>
<ArticleIdList><ArticleId IdType="pubmed">20532354</ArticleId>
</ArticleIdList>
</Reference>
</ReferenceList>
<ReferenceList><Reference><Citation>Nucleosides Nucleotides Nucleic Acids. 2011 May;30(5):340-52</Citation>
<ArticleIdList><ArticleId IdType="pubmed">21774629</ArticleId>
</ArticleIdList>
</Reference>
</ReferenceList>
<ReferenceList><Reference><Citation>J Nat Prod. 2006 Mar;69(3):439-42</Citation>
<ArticleIdList><ArticleId IdType="pubmed">16562855</ArticleId>
</ArticleIdList>
</Reference>
</ReferenceList>
<ReferenceList><Reference><Citation>Mol Divers. 2012 May;16(2):325-33</Citation>
<ArticleIdList><ArticleId IdType="pubmed">22528269</ArticleId>
</ArticleIdList>
</Reference>
</ReferenceList>
<ReferenceList><Reference><Citation>ChemMedChem. 2007 Aug;2(8):1141-7</Citation>
<ArticleIdList><ArticleId IdType="pubmed">17477343</ArticleId>
</ArticleIdList>
</Reference>
</ReferenceList>
<ReferenceList><Reference><Citation>Nat Rev Microbiol. 2004 Sep;2(9):704-20</Citation>
<ArticleIdList><ArticleId IdType="pubmed">15372081</ArticleId>
</ArticleIdList>
</Reference>
</ReferenceList>
<ReferenceList><Reference><Citation>Eur J Med Chem. 2011 May;46(5):1803-12</Citation>
<ArticleIdList><ArticleId IdType="pubmed">21397370</ArticleId>
</ArticleIdList>
</Reference>
</ReferenceList>
<ReferenceList><Reference><Citation>Med Res Rev. 1999 Nov;19(6):497-520</Citation>
<ArticleIdList><ArticleId IdType="pubmed">10557367</ArticleId>
</ArticleIdList>
</Reference>
</ReferenceList>
<ReferenceList><Reference><Citation>J Nat Prod. 2010 Jul 23;73(7):1250-3</Citation>
<ArticleIdList><ArticleId IdType="pubmed">20550123</ArticleId>
</ArticleIdList>
</Reference>
</ReferenceList>
<ReferenceList><Reference><Citation>J Med Chem. 2010 Jan 28;53(2):660-8</Citation>
<ArticleIdList><ArticleId IdType="pubmed">20000776</ArticleId>
</ArticleIdList>
</Reference>
</ReferenceList>
<ReferenceList><Reference><Citation>Proc Natl Acad Sci U S A. 1991 Aug 1;88(15):6863-7</Citation>
<ArticleIdList><ArticleId IdType="pubmed">1713693</ArticleId>
</ArticleIdList>
</Reference>
</ReferenceList>
<ReferenceList><Reference><Citation>Med Res Rev. 2000 Jul;20(4):231-93</Citation>
<ArticleIdList><ArticleId IdType="pubmed">10861727</ArticleId>
</ArticleIdList>
</Reference>
</ReferenceList>
<ReferenceList><Reference><Citation>Nucleosides Nucleotides Nucleic Acids. 2011 Feb;30(2):120-34</Citation>
<ArticleIdList><ArticleId IdType="pubmed">21360410</ArticleId>
</ArticleIdList>
</Reference>
</ReferenceList>
<ReferenceList><Reference><Citation>Bioorg Med Chem Lett. 2010 Feb 1;20(3):809-13</Citation>
<ArticleIdList><ArticleId IdType="pubmed">20064723</ArticleId>
</ArticleIdList>
</Reference>
</ReferenceList>
<ReferenceList><Reference><Citation>Bioorg Med Chem Lett. 2011 Dec 15;21(24):7344-50</Citation>
<ArticleIdList><ArticleId IdType="pubmed">22071300</ArticleId>
</ArticleIdList>
</Reference>
</ReferenceList>
<ReferenceList><Reference><Citation>Eur J Med Chem. 2010 Jan;45(1):90-7</Citation>
<ArticleIdList><ArticleId IdType="pubmed">19836860</ArticleId>
</ArticleIdList>
</Reference>
</ReferenceList>
<ReferenceList><Reference><Citation>Nucleosides Nucleotides Nucleic Acids. 2002;21(1):15-21</Citation>
<ArticleIdList><ArticleId IdType="pubmed">11991146</ArticleId>
</ArticleIdList>
</Reference>
</ReferenceList>
</PubmedData>
</pubmed>
</record>
Pour manipuler ce document sous Unix (Dilib)
EXPLOR_STEP=$WICRI_ROOT/Sante/explor/SrasV1/Data/PubMed/Curation
HfdSelect -h $EXPLOR_STEP/biblio.hfd -nk 001056 | SxmlIndent | more
Ou
HfdSelect -h $EXPLOR_AREA/Data/PubMed/Curation/biblio.hfd -nk 001056 | SxmlIndent | more
Pour mettre un lien sur cette page dans le réseau Wicri
{{Explor lien |wiki= Sante |area= SrasV1 |flux= PubMed |étape= Curation |type= RBID |clé= pubmed:24486419 |texte= Synthesis and biological evaluation of 2-oxonicotinonitriles and 2-oxonicotinonitrile based nucleoside analogues. }}
Pour générer des pages wiki
HfdIndexSelect -h $EXPLOR_AREA/Data/PubMed/Curation/RBID.i -Sk "pubmed:24486419" \ | HfdSelect -Kh $EXPLOR_AREA/Data/PubMed/Curation/biblio.hfd \ | NlmPubMed2Wicri -a SrasV1
![]() | This area was generated with Dilib version V0.6.33. | ![]() |