Acyclic nucleoside phosphonates with a branched 2-(2-phosphonoethoxy)ethyl chain: Efficient synthesis and antiviral activity

Series of novel acyclic nucleoside phosphonates (ANPs) with various nucleobases and 2-(2-phosphonoethoxy)ethyl (PEE) chain bearing various substituents in β-position to the phosphonate moiety were prepared. The influence of structural alternations on antiviral activity was studied. Several derivativ...

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Detalles Bibliográficos
Autores principales: Hocková, Dana, Holý, Antonín, Andrei, Graciela, Snoeck, Robert, Balzarini, Jan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Elsevier Ltd. 2011
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7125515/
https://www.ncbi.nlm.nih.gov/pubmed/21745746
http://dx.doi.org/10.1016/j.bmc.2011.06.045
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author Hocková, Dana
Holý, Antonín
Andrei, Graciela
Snoeck, Robert
Balzarini, Jan
author_facet Hocková, Dana
Holý, Antonín
Andrei, Graciela
Snoeck, Robert
Balzarini, Jan
author_sort Hocková, Dana
collection PubMed
description Series of novel acyclic nucleoside phosphonates (ANPs) with various nucleobases and 2-(2-phosphonoethoxy)ethyl (PEE) chain bearing various substituents in β-position to the phosphonate moiety were prepared. The influence of structural alternations on antiviral activity was studied. Several derivatives exhibit antiviral activity against HIV and vaccinia virus (middle micromolar range), HSV-1 and HSV-2 (lower micromolar range) and VZV and CMV (nanomolar range), although the parent unbranched PEE–ANPs are inactive. Adenine as a nucleobase and the methyl group attached to the PEE chain proved to be a prerequisite to afford pronounced antiviral activity.
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spelling pubmed-71255152020-04-08 Acyclic nucleoside phosphonates with a branched 2-(2-phosphonoethoxy)ethyl chain: Efficient synthesis and antiviral activity Hocková, Dana Holý, Antonín Andrei, Graciela Snoeck, Robert Balzarini, Jan Bioorg Med Chem Article Series of novel acyclic nucleoside phosphonates (ANPs) with various nucleobases and 2-(2-phosphonoethoxy)ethyl (PEE) chain bearing various substituents in β-position to the phosphonate moiety were prepared. The influence of structural alternations on antiviral activity was studied. Several derivatives exhibit antiviral activity against HIV and vaccinia virus (middle micromolar range), HSV-1 and HSV-2 (lower micromolar range) and VZV and CMV (nanomolar range), although the parent unbranched PEE–ANPs are inactive. Adenine as a nucleobase and the methyl group attached to the PEE chain proved to be a prerequisite to afford pronounced antiviral activity. Elsevier Ltd. 2011-08-01 2011-06-22 /pmc/articles/PMC7125515/ /pubmed/21745746 http://dx.doi.org/10.1016/j.bmc.2011.06.045 Text en Copyright © 2011 Elsevier Ltd. All rights reserved. Since January 2020 Elsevier has created a COVID-19 resource centre with free information in English and Mandarin on the novel coronavirus COVID-19. The COVID-19 resource centre is hosted on Elsevier Connect, the company's public news and information website. Elsevier hereby grants permission to make all its COVID-19-related research that is available on the COVID-19 resource centre - including this research content - immediately available in PubMed Central and other publicly funded repositories, such as the WHO COVID database with rights for unrestricted research re-use and analyses in any form or by any means with acknowledgement of the original source. These permissions are granted for free by Elsevier for as long as the COVID-19 resource centre remains active.
spellingShingle Article
Hocková, Dana
Holý, Antonín
Andrei, Graciela
Snoeck, Robert
Balzarini, Jan
Acyclic nucleoside phosphonates with a branched 2-(2-phosphonoethoxy)ethyl chain: Efficient synthesis and antiviral activity
title Acyclic nucleoside phosphonates with a branched 2-(2-phosphonoethoxy)ethyl chain: Efficient synthesis and antiviral activity
title_full Acyclic nucleoside phosphonates with a branched 2-(2-phosphonoethoxy)ethyl chain: Efficient synthesis and antiviral activity
title_fullStr Acyclic nucleoside phosphonates with a branched 2-(2-phosphonoethoxy)ethyl chain: Efficient synthesis and antiviral activity
title_full_unstemmed Acyclic nucleoside phosphonates with a branched 2-(2-phosphonoethoxy)ethyl chain: Efficient synthesis and antiviral activity
title_short Acyclic nucleoside phosphonates with a branched 2-(2-phosphonoethoxy)ethyl chain: Efficient synthesis and antiviral activity
title_sort acyclic nucleoside phosphonates with a branched 2-(2-phosphonoethoxy)ethyl chain: efficient synthesis and antiviral activity
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7125515/
https://www.ncbi.nlm.nih.gov/pubmed/21745746
http://dx.doi.org/10.1016/j.bmc.2011.06.045
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