Synthesis and biological evaluation of 2-oxonicotinonitriles and 2-oxonicotinonitrile based nucleoside analogues.
Identifieur interne : 000F15 ( PubMed/Checkpoint ); précédent : 000F14; suivant : 000F16Synthesis 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
Affiliations:
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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><wicri:noRegion>Zagazig</wicri:noRegion></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><wicri:noRegion>Zagazig</wicri:noRegion></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><wicri:noRegion>Zagazig</wicri:noRegion></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. 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