Synthesis and antiviral evaluation of acyclic azanucleosides developed from sulfanilamide as a lead structure

The acyclic azanucleosides with 2-, 3-, or 4-aminobenzenesulfonyl function at the nitrogen atom of the sugar mimic were prepared by coupling of 2-, 3-, or 4-nitro-N-(2-pivaloyloxyethyl)-N-(pivaloyloxymethyl)benzenesulfonamide with the silylated pyrimidine nucleobases followed by the reduction of the...

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Autores principales: Gawin, Rafał, De Clercq, Erik, Naesens, Lieve, Koszytkowska-Stawińska, Mariola
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Elsevier Ltd. 2008
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7127773/
https://www.ncbi.nlm.nih.gov/pubmed/18778942
http://dx.doi.org/10.1016/j.bmc.2008.08.041
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author Gawin, Rafał
De Clercq, Erik
Naesens, Lieve
Koszytkowska-Stawińska, Mariola
author_facet Gawin, Rafał
De Clercq, Erik
Naesens, Lieve
Koszytkowska-Stawińska, Mariola
author_sort Gawin, Rafał
collection PubMed
description The acyclic azanucleosides with 2-, 3-, or 4-aminobenzenesulfonyl function at the nitrogen atom of the sugar mimic were prepared by coupling of 2-, 3-, or 4-nitro-N-(2-pivaloyloxyethyl)-N-(pivaloyloxymethyl)benzenesulfonamide with the silylated pyrimidine nucleobases followed by the reduction of the nitro group with sodium dithionite in aqueous solution or the palladium-catalysed transfer hydrogenation. The azanucleosides were evaluated for, but found to be devoid of, activity against several RNA- and DNA-viruses in vitro.
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spelling pubmed-71277732020-04-08 Synthesis and antiviral evaluation of acyclic azanucleosides developed from sulfanilamide as a lead structure Gawin, Rafał De Clercq, Erik Naesens, Lieve Koszytkowska-Stawińska, Mariola Bioorg Med Chem Article The acyclic azanucleosides with 2-, 3-, or 4-aminobenzenesulfonyl function at the nitrogen atom of the sugar mimic were prepared by coupling of 2-, 3-, or 4-nitro-N-(2-pivaloyloxyethyl)-N-(pivaloyloxymethyl)benzenesulfonamide with the silylated pyrimidine nucleobases followed by the reduction of the nitro group with sodium dithionite in aqueous solution or the palladium-catalysed transfer hydrogenation. The azanucleosides were evaluated for, but found to be devoid of, activity against several RNA- and DNA-viruses in vitro. Elsevier Ltd. 2008-09-15 2008-08-26 /pmc/articles/PMC7127773/ /pubmed/18778942 http://dx.doi.org/10.1016/j.bmc.2008.08.041 Text en Copyright © 2008 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
Gawin, Rafał
De Clercq, Erik
Naesens, Lieve
Koszytkowska-Stawińska, Mariola
Synthesis and antiviral evaluation of acyclic azanucleosides developed from sulfanilamide as a lead structure
title Synthesis and antiviral evaluation of acyclic azanucleosides developed from sulfanilamide as a lead structure
title_full Synthesis and antiviral evaluation of acyclic azanucleosides developed from sulfanilamide as a lead structure
title_fullStr Synthesis and antiviral evaluation of acyclic azanucleosides developed from sulfanilamide as a lead structure
title_full_unstemmed Synthesis and antiviral evaluation of acyclic azanucleosides developed from sulfanilamide as a lead structure
title_short Synthesis and antiviral evaluation of acyclic azanucleosides developed from sulfanilamide as a lead structure
title_sort synthesis and antiviral evaluation of acyclic azanucleosides developed from sulfanilamide as a lead structure
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7127773/
https://www.ncbi.nlm.nih.gov/pubmed/18778942
http://dx.doi.org/10.1016/j.bmc.2008.08.041
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