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Design, Synthesis, and Antiviral Activity of Novel Ribonucleosides of 1,2,3‐Triazolylbenzyl‐aminophosphonates

A novel series of ribonucleosides of 1,2,3‐triazolylbenzyl‐aminophosphonates was synthesized through the Kabachnik–Fields reaction using I(2) as catalyst followed by copper‐catalyzed cycloaddition of the azide–alkyne reaction (CuAAC). All structures of the newly prepared compounds were characterized...

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Autores principales: Ouahrouch, Abdelaaziz, Taourirte, Moha, Schols, Dominique, Snoeck, Robert, Andrei, Graciela, Engels, Joachim W., Lazrek, Hassan B.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4832832/
https://www.ncbi.nlm.nih.gov/pubmed/26575425
http://dx.doi.org/10.1002/ardp.201500292
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author Ouahrouch, Abdelaaziz
Taourirte, Moha
Schols, Dominique
Snoeck, Robert
Andrei, Graciela
Engels, Joachim W.
Lazrek, Hassan B.
author_facet Ouahrouch, Abdelaaziz
Taourirte, Moha
Schols, Dominique
Snoeck, Robert
Andrei, Graciela
Engels, Joachim W.
Lazrek, Hassan B.
author_sort Ouahrouch, Abdelaaziz
collection PubMed
description A novel series of ribonucleosides of 1,2,3‐triazolylbenzyl‐aminophosphonates was synthesized through the Kabachnik–Fields reaction using I(2) as catalyst followed by copper‐catalyzed cycloaddition of the azide–alkyne reaction (CuAAC). All structures of the newly prepared compounds were characterized by (1)H NMR, (13)C 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.
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spelling pubmed-48328322016-04-27 Design, Synthesis, and Antiviral Activity of Novel Ribonucleosides of 1,2,3‐Triazolylbenzyl‐aminophosphonates Ouahrouch, Abdelaaziz Taourirte, Moha Schols, Dominique Snoeck, Robert Andrei, Graciela Engels, Joachim W. Lazrek, Hassan B. Arch Pharm (Weinheim) Full Papers A novel series of ribonucleosides of 1,2,3‐triazolylbenzyl‐aminophosphonates was synthesized through the Kabachnik–Fields reaction using I(2) as catalyst followed by copper‐catalyzed cycloaddition of the azide–alkyne reaction (CuAAC). All structures of the newly prepared compounds were characterized by (1)H NMR, (13)C 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. John Wiley and Sons Inc. 2015-11-17 2016-01 /pmc/articles/PMC4832832/ /pubmed/26575425 http://dx.doi.org/10.1002/ardp.201500292 Text en © 2015 The Authors. Archiv der Pharmazie Published by Wiley‐VCH Verlag GmbH & Co. KGaA This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial‐NoDerivs (http://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Full Papers
Ouahrouch, Abdelaaziz
Taourirte, Moha
Schols, Dominique
Snoeck, Robert
Andrei, Graciela
Engels, Joachim W.
Lazrek, Hassan B.
Design, Synthesis, and Antiviral Activity of Novel Ribonucleosides of 1,2,3‐Triazolylbenzyl‐aminophosphonates
title Design, Synthesis, and Antiviral Activity of Novel Ribonucleosides of 1,2,3‐Triazolylbenzyl‐aminophosphonates
title_full Design, Synthesis, and Antiviral Activity of Novel Ribonucleosides of 1,2,3‐Triazolylbenzyl‐aminophosphonates
title_fullStr Design, Synthesis, and Antiviral Activity of Novel Ribonucleosides of 1,2,3‐Triazolylbenzyl‐aminophosphonates
title_full_unstemmed Design, Synthesis, and Antiviral Activity of Novel Ribonucleosides of 1,2,3‐Triazolylbenzyl‐aminophosphonates
title_short Design, Synthesis, and Antiviral Activity of Novel Ribonucleosides of 1,2,3‐Triazolylbenzyl‐aminophosphonates
title_sort design, synthesis, and antiviral activity of novel ribonucleosides of 1,2,3‐triazolylbenzyl‐aminophosphonates
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4832832/
https://www.ncbi.nlm.nih.gov/pubmed/26575425
http://dx.doi.org/10.1002/ardp.201500292
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