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An efficient microwave-assisted synthesis and biological properties of polysubstituted pyrimidinyl- and 1,3,5-triazinylphosphonic acids
Polysubstituted pyrimidinylphosphonic and 1,3,5-triazinylphosphonic acids with potential biological properties were prepared in high yields by the microwave-assisted Michaelis–Arbuzov reaction of trialkyl phosphite with the corresponding halopyrimidines and halo-1,3,5-triazines, respectively, follow...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Elsevier Ltd.
2012
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7125588/ https://www.ncbi.nlm.nih.gov/pubmed/32287424 http://dx.doi.org/10.1016/j.tet.2011.11.040 |
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author | Jansa, Petr Hradil, Ondřej Baszczyňski, Ondřej Dračínský, Martin Klepetářová, Blanka Holý, Antonín Balzarini, Jan Janeba, Zlatko |
author_facet | Jansa, Petr Hradil, Ondřej Baszczyňski, Ondřej Dračínský, Martin Klepetářová, Blanka Holý, Antonín Balzarini, Jan Janeba, Zlatko |
author_sort | Jansa, Petr |
collection | PubMed |
description | Polysubstituted pyrimidinylphosphonic and 1,3,5-triazinylphosphonic acids with potential biological properties were prepared in high yields by the microwave-assisted Michaelis–Arbuzov reaction of trialkyl phosphite with the corresponding halopyrimidines and halo-1,3,5-triazines, respectively, followed by the standard deprotection of the phosphonate group using TMSBr in acetonitrile. 4,6-Diamino-5-chloropyrimidin-2-ylphosphonic acid (7a) was found to exhibit a weak to moderate anti-influenza activity (28–50 μM) and may represent a novel hit for further SAR studies and antiviral improvement. |
format | Online Article Text |
id | pubmed-7125588 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2012 |
publisher | Elsevier Ltd. |
record_format | MEDLINE/PubMed |
spelling | pubmed-71255882020-04-08 An efficient microwave-assisted synthesis and biological properties of polysubstituted pyrimidinyl- and 1,3,5-triazinylphosphonic acids Jansa, Petr Hradil, Ondřej Baszczyňski, Ondřej Dračínský, Martin Klepetářová, Blanka Holý, Antonín Balzarini, Jan Janeba, Zlatko Tetrahedron Article Polysubstituted pyrimidinylphosphonic and 1,3,5-triazinylphosphonic acids with potential biological properties were prepared in high yields by the microwave-assisted Michaelis–Arbuzov reaction of trialkyl phosphite with the corresponding halopyrimidines and halo-1,3,5-triazines, respectively, followed by the standard deprotection of the phosphonate group using TMSBr in acetonitrile. 4,6-Diamino-5-chloropyrimidin-2-ylphosphonic acid (7a) was found to exhibit a weak to moderate anti-influenza activity (28–50 μM) and may represent a novel hit for further SAR studies and antiviral improvement. Elsevier Ltd. 2012-01-21 2011-11-19 /pmc/articles/PMC7125588/ /pubmed/32287424 http://dx.doi.org/10.1016/j.tet.2011.11.040 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 Jansa, Petr Hradil, Ondřej Baszczyňski, Ondřej Dračínský, Martin Klepetářová, Blanka Holý, Antonín Balzarini, Jan Janeba, Zlatko An efficient microwave-assisted synthesis and biological properties of polysubstituted pyrimidinyl- and 1,3,5-triazinylphosphonic acids |
title | An efficient microwave-assisted synthesis and biological properties of polysubstituted pyrimidinyl- and 1,3,5-triazinylphosphonic acids |
title_full | An efficient microwave-assisted synthesis and biological properties of polysubstituted pyrimidinyl- and 1,3,5-triazinylphosphonic acids |
title_fullStr | An efficient microwave-assisted synthesis and biological properties of polysubstituted pyrimidinyl- and 1,3,5-triazinylphosphonic acids |
title_full_unstemmed | An efficient microwave-assisted synthesis and biological properties of polysubstituted pyrimidinyl- and 1,3,5-triazinylphosphonic acids |
title_short | An efficient microwave-assisted synthesis and biological properties of polysubstituted pyrimidinyl- and 1,3,5-triazinylphosphonic acids |
title_sort | efficient microwave-assisted synthesis and biological properties of polysubstituted pyrimidinyl- and 1,3,5-triazinylphosphonic acids |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7125588/ https://www.ncbi.nlm.nih.gov/pubmed/32287424 http://dx.doi.org/10.1016/j.tet.2011.11.040 |
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