Design, Synthesis, and Antiviral Activity of Novel Ribonucleosides of 1,2,3‐Triazolylbenzyl‐aminophosphonates
Identifieur interne : 000906 ( Main/Merge ); précédent : 000905; suivant : 000907Design, Synthesis, and Antiviral Activity of Novel Ribonucleosides of 1,2,3‐Triazolylbenzyl‐aminophosphonates
Auteurs : Abdelaaziz Ouahrouch [Maroc, Allemagne] ; Moha Taourirte [Maroc] ; Dominique Schols [Belgique] ; Robert Snoeck [Belgique] ; Graciela Andrei [Belgique] ; Joachim W. Engels [Allemagne] ; Hassan B. Lazrek [Maroc]Source :
- Archiv der Pharmazie [ 0365-6233 ] ; 2016-01.
Abstract
A novel series of ribonucleosides of 1,2,3‐triazolylbenzyl‐aminophosphonates was synthesized through the Kabachnik–Fields reaction using I2 as catalyst followed by copper‐catalyzed cycloaddition of the azide–alkyne reaction (CuAAC). All structures of the newly prepared compounds were characterized by 1H NMR, 13C NMR, and HRMS spectra. The structures of 2e, 2f, 3d, and 3g were further confirmed by X‐ray diffraction analysis. These compounds were tested against various strains of DNA and RNA viruses; compounds 4b and 4c showed a modest inhibitory activity against respiratory syncytial virus (RSV) and compound 4h displayed modest inhibitory activity against Coxsackie virus B4.
Ribonucleosides of 1,2,3‐triazolylbenzyl‐aminophosphonate analogs were synthesized through the Kabachnik–Fields reaction and copper‐catalyzed cycloaddition of the azide–alkyne reaction. All compounds were tested against various strains of DNA and RNA viruses. Compounds 4b and 4c showed modest inhibitory activity against respiratory syncytial virus while compound 4h displayed modest inhibitory activity against Coxsackie virus B4.
Url:
- https://api.istex.fr/ark:/67375/WNG-P4G7Q498-8/fulltext.pdf
- http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4832832
DOI: 10.1002/ardp.201500292
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All structures of the newly prepared compounds were characterized by 1H NMR, 13C NMR, and HRMS spectra. The structures of 2e, 2f, 3d, and 3g were further confirmed by X‐ray diffraction analysis. These compounds were tested against various strains of DNA and RNA viruses; compounds 4b and 4c showed a modest inhibitory activity against respiratory syncytial virus (RSV) and compound 4h displayed modest inhibitory activity against Coxsackie virus B4.</div><div type="abstract" xml:lang="en">Ribonucleosides of 1,2,3‐triazolylbenzyl‐aminophosphonate analogs were synthesized through the Kabachnik–Fields reaction and copper‐catalyzed cycloaddition of the azide–alkyne reaction. All compounds were tested against various strains of DNA and RNA viruses. 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Engels</name><affiliation wicri:level="3"><country xml:lang="fr">Allemagne</country><wicri:regionArea>Institute for Organic Chemistry and Chemical Biology, Goethe‐University Frankfurt am Main, Frankfurt am Main</wicri:regionArea><placeName><region type="land" nuts="1">Hesse (Land)</region><region type="district" nuts="2">District de Darmstadt</region><settlement type="city">Francfort-sur-le-Main</settlement></placeName></affiliation><affiliation></affiliation><affiliation wicri:level="1"><country wicri:rule="url">Allemagne</country></affiliation></author><author><name sortKey="Lazrek, Hassan B" sort="Lazrek, Hassan B" uniqKey="Lazrek H" first="Hassan B." last="Lazrek">Hassan B. Lazrek</name><affiliation wicri:level="1"><country xml:lang="fr">Maroc</country><wicri:regionArea>Department of Chemistry, Faculty of Sciences Semlalia, Laboratory of Biomolecular and Medicinal Chemistry, Marrakesh</wicri:regionArea><wicri:noRegion>Marrakesh</wicri:noRegion></affiliation></author></analytic><monogr></monogr><series><title level="j" type="main">Archiv der Pharmazie</title><title level="j" type="alt">ARCHIV DER PHARMAZIE</title><idno type="ISSN">0365-6233</idno><idno type="eISSN">1521-4184</idno><imprint><biblScope unit="vol">349</biblScope><biblScope unit="issue">1</biblScope><biblScope unit="page" from="30">30</biblScope><biblScope unit="page" to="41">41</biblScope><biblScope unit="page-count">12</biblScope><date type="published" when="2016-01">2016-01</date></imprint><idno type="ISSN">0365-6233</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0365-6233</idno></seriesStmt></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">A novel series of ribonucleosides of 1,2,3‐triazolylbenzyl‐aminophosphonates was synthesized through the Kabachnik–Fields reaction using I2 as catalyst followed by copper‐catalyzed cycloaddition of the azide–alkyne reaction (CuAAC). All structures of the newly prepared compounds were characterized by 1H NMR, 13C NMR, and HRMS spectra. The structures of 2e, 2f, 3d, and 3g were further confirmed by X‐ray diffraction analysis. These compounds were tested against various strains of DNA and RNA viruses; compounds 4b and 4c showed a modest inhibitory activity against respiratory syncytial virus (RSV) and compound 4h displayed modest inhibitory activity against Coxsackie virus B4.</div><div type="abstract" xml:lang="en">Ribonucleosides of 1,2,3‐triazolylbenzyl‐aminophosphonate analogs were synthesized through the Kabachnik–Fields reaction and copper‐catalyzed cycloaddition of the azide–alkyne reaction. All compounds were tested against various strains of DNA and RNA viruses. 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Engels</name><affiliation><nlm:aff id="ardp201500292-aff-0003"></nlm:aff></affiliation></author><author><name sortKey="Lazrek, Hassan B" sort="Lazrek, Hassan B" uniqKey="Lazrek H" first="Hassan B." last="Lazrek">Hassan B. Lazrek</name><affiliation><nlm:aff id="ardp201500292-aff-0002"></nlm:aff></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">26575425</idno><idno type="pmc">4832832</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4832832</idno><idno type="RBID">PMC:4832832</idno><idno type="doi">10.1002/ardp.201500292</idno><date when="2015">2015</date><idno type="wicri:Area/Pmc/Corpus">000042</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000042</idno><idno type="wicri:Area/Pmc/Curation">000042</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Curation">000042</idno><idno type="wicri:Area/Pmc/Checkpoint">000357</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Checkpoint">000357</idno><idno type="wicri:Area/Ncbi/Merge">000507</idno><idno type="wicri:Area/Ncbi/Curation">000507</idno><idno type="wicri:Area/Ncbi/Checkpoint">000507</idno><idno type="wicri:doubleKey">0365-6233:2015:Ouahrouch A:design:synthesis:and</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Design, Synthesis, and Antiviral Activity of Novel Ribonucleosides of 1,2,3‐Triazolylbenzyl‐aminophosphonates</title><author><name sortKey="Ouahrouch, Abdelaaziz" sort="Ouahrouch, Abdelaaziz" uniqKey="Ouahrouch A" first="Abdelaaziz" last="Ouahrouch">Abdelaaziz Ouahrouch</name><affiliation><nlm:aff id="ardp201500292-aff-0001"></nlm:aff></affiliation><affiliation><nlm:aff id="ardp201500292-aff-0002"></nlm:aff></affiliation><affiliation><nlm:aff id="ardp201500292-aff-0003"></nlm:aff></affiliation></author><author><name sortKey="Taourirte, Moha" sort="Taourirte, Moha" uniqKey="Taourirte M" first="Moha" last="Taourirte">Moha Taourirte</name><affiliation><nlm:aff id="ardp201500292-aff-0001"></nlm:aff></affiliation></author><author><name sortKey="Schols, Dominique" sort="Schols, Dominique" uniqKey="Schols D" first="Dominique" last="Schols">Dominique Schols</name><affiliation><nlm:aff id="ardp201500292-aff-0004"></nlm:aff></affiliation></author><author><name sortKey="Snoeck, Robert" sort="Snoeck, Robert" uniqKey="Snoeck R" first="Robert" last="Snoeck">Robert Snoeck</name><affiliation><nlm:aff id="ardp201500292-aff-0004"></nlm:aff></affiliation></author><author><name sortKey="Andrei, Graciela" sort="Andrei, Graciela" uniqKey="Andrei G" first="Graciela" last="Andrei">Graciela Andrei</name><affiliation><nlm:aff id="ardp201500292-aff-0004"></nlm:aff></affiliation></author><author><name sortKey="Engels, Joachim W" sort="Engels, Joachim W" uniqKey="Engels J" first="Joachim W." last="Engels">Joachim W. Engels</name><affiliation><nlm:aff id="ardp201500292-aff-0003"></nlm:aff></affiliation></author><author><name sortKey="Lazrek, Hassan B" sort="Lazrek, Hassan B" uniqKey="Lazrek H" first="Hassan B." last="Lazrek">Hassan B. Lazrek</name><affiliation><nlm:aff id="ardp201500292-aff-0002"></nlm:aff></affiliation></author></analytic><series><title level="j">Archiv Der Pharmazie</title><idno type="ISSN">0365-6233</idno><idno type="eISSN">1521-4184</idno><imprint><date when="2015">2015</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p>A novel series of ribonucleosides of 1,2,3‐triazolylbenzyl‐aminophosphonates was synthesized through the Kabachnik–Fields reaction using I<sub>2</sub> as catalyst followed by copper‐catalyzed cycloaddition of the azide–alkyne reaction (CuAAC). All structures of the newly prepared compounds were characterized by <sup>1</sup>H NMR, <sup>13</sup>C NMR, and HRMS spectra. The structures of <bold>2e</bold>, <bold>2f</bold>, <bold>3d</bold>, and <bold>3g</bold> were further confirmed by X‐ray diffraction analysis. These compounds were tested against various strains of DNA and RNA viruses; compounds <bold>4b</bold> and <bold>4c</bold> showed a modest inhibitory activity against respiratory syncytial virus (RSV) and compound <bold>4h</bold> displayed modest inhibitory activity against Coxsackie virus B4.</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct></listBibl></div1></back></TEI></PMC></double></record>Pour manipuler ce document sous Unix (Dilib)
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