Synthesis and biological evaluation of 2-oxonicotinonitriles and 2-oxonicotinonitrile based nucleoside analogues.
Identifieur interne : 001056 ( PubMed/Corpus ); précédent : 001055; suivant : 001057Synthesis and biological evaluation of 2-oxonicotinonitriles and 2-oxonicotinonitrile based nucleoside analogues.
Auteurs : Reham A I. Abou-Elkhair ; Ahmed H. Moustafa ; Abdelfattah Z. Haikal ; Ahmed M. IbraheemSource :
- European journal of medicinal chemistry [ 1768-3254 ] ; 2014.
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
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<author><name sortKey="Moustafa, Ahmed H" sort="Moustafa, Ahmed H" uniqKey="Moustafa A" first="Ahmed H" last="Moustafa">Ahmed H. Moustafa</name>
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<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>
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<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>
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