A novel type of acyclic nucleoside phosphonates derived from 2-(phosphonomethoxy)propanoic acid

A convenient and efficient synthesis of a novel class of acyclic nucleoside phosphonates derived from 2-(phosphonomethoxy)propanoic acid has been developed. The key step of the synthesis is the optimized oxidation of the 3-hydroxy-2-(phosphonomethoxy)propyl (HPMP) analogues to the corresponding 2′-c...

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Detalles Bibliográficos
Autores principales: Kaiser, Martin Maxmilian, Jansa, Petr, Dračínský, Martin, Janeba, Zlatko
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Elsevier Ltd. 2012
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7111817/
https://www.ncbi.nlm.nih.gov/pubmed/32287422
http://dx.doi.org/10.1016/j.tet.2012.03.066
Descripción
Sumario:A convenient and efficient synthesis of a novel class of acyclic nucleoside phosphonates derived from 2-(phosphonomethoxy)propanoic acid has been developed. The key step of the synthesis is the optimized oxidation of the 3-hydroxy-2-(phosphonomethoxy)propyl (HPMP) analogues to the corresponding 2′-carboxy-PME (CPME) derivatives using the TEMPO/NaClO(2)/NaClO oxidizing system. Although (S)-3-(adenin-9-yl)-2-(phosphonomethoxy)propanoic acid ((S)-CPMEA) has been designed as a compound with potential anti-HIV activity, none of the newly prepared CPME analogues exhibited any antiviral activity.

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