Design, synthesis, antiviral and cytostatic evaluation of novel isoxazolidine nucleotide analogues with a carbamoyl linker

5-Arylcarbamoyl-2-methylisoxazolidin-3-yl-3-phosphonates have been synthesised from N-methyl-C-diethoxyphosphorylnitrone and N-arylacrylamides in good yields. cis- and trans-isoxazolidine phosphonates obtained herein were evaluated for activity against a broad range of DNA and RNA viruses. None of t...

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Autores principales: Kokosza, Kamil, Balzarini, Jan, Piotrowska, Dorota G.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Elsevier Ltd. 2013
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7127400/
https://www.ncbi.nlm.nih.gov/pubmed/23380474
http://dx.doi.org/10.1016/j.bmc.2013.01.007
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author Kokosza, Kamil
Balzarini, Jan
Piotrowska, Dorota G.
author_facet Kokosza, Kamil
Balzarini, Jan
Piotrowska, Dorota G.
author_sort Kokosza, Kamil
collection PubMed
description 5-Arylcarbamoyl-2-methylisoxazolidin-3-yl-3-phosphonates have been synthesised from N-methyl-C-diethoxyphosphorylnitrone and N-arylacrylamides in good yields. cis- and trans-isoxazolidine phosphonates obtained herein were evaluated for activity against a broad range of DNA and RNA viruses. None of the compounds were endowed with antiviral activity at subtoxic concentrations. Isoxazolidines having phenyl substituted with halogen (Ar = 2-F-C(6)H(4); 3-Br-C(6)H(4); and 4-Br-C(6)H(4)) have been found to inhibit proliferation of L1210, CEM as well as HeLa cells with IC(50) in the 100–170 μM range.
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spelling pubmed-71274002020-04-08 Design, synthesis, antiviral and cytostatic evaluation of novel isoxazolidine nucleotide analogues with a carbamoyl linker Kokosza, Kamil Balzarini, Jan Piotrowska, Dorota G. Bioorg Med Chem Article 5-Arylcarbamoyl-2-methylisoxazolidin-3-yl-3-phosphonates have been synthesised from N-methyl-C-diethoxyphosphorylnitrone and N-arylacrylamides in good yields. cis- and trans-isoxazolidine phosphonates obtained herein were evaluated for activity against a broad range of DNA and RNA viruses. None of the compounds were endowed with antiviral activity at subtoxic concentrations. Isoxazolidines having phenyl substituted with halogen (Ar = 2-F-C(6)H(4); 3-Br-C(6)H(4); and 4-Br-C(6)H(4)) have been found to inhibit proliferation of L1210, CEM as well as HeLa cells with IC(50) in the 100–170 μM range. Elsevier Ltd. 2013-03-01 2013-01-15 /pmc/articles/PMC7127400/ /pubmed/23380474 http://dx.doi.org/10.1016/j.bmc.2013.01.007 Text en Copyright © 2013 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
Kokosza, Kamil
Balzarini, Jan
Piotrowska, Dorota G.
Design, synthesis, antiviral and cytostatic evaluation of novel isoxazolidine nucleotide analogues with a carbamoyl linker
title Design, synthesis, antiviral and cytostatic evaluation of novel isoxazolidine nucleotide analogues with a carbamoyl linker
title_full Design, synthesis, antiviral and cytostatic evaluation of novel isoxazolidine nucleotide analogues with a carbamoyl linker
title_fullStr Design, synthesis, antiviral and cytostatic evaluation of novel isoxazolidine nucleotide analogues with a carbamoyl linker
title_full_unstemmed Design, synthesis, antiviral and cytostatic evaluation of novel isoxazolidine nucleotide analogues with a carbamoyl linker
title_short Design, synthesis, antiviral and cytostatic evaluation of novel isoxazolidine nucleotide analogues with a carbamoyl linker
title_sort design, synthesis, antiviral and cytostatic evaluation of novel isoxazolidine nucleotide analogues with a carbamoyl linker
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7127400/
https://www.ncbi.nlm.nih.gov/pubmed/23380474
http://dx.doi.org/10.1016/j.bmc.2013.01.007
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