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

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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Veröffentlicht in:Tetrahedron 2012-05, Vol.68 (21), p.4003-4012
Hauptverfasser: Kaiser, Martin Maxmilian, Jansa, Petr, Dračínský, Martin, Janeba, Zlatko
Format: Artikel
Sprache:eng
Schlagworte:
Acyclic nucleoside phosphonates
Antiviral
antiviral properties
chemical structure
CPMEA
Derivatives
HPMPA
Microwave
Nucleosides
Oxidation
Phosphonates
PMEA
propionic acid
Synthesis
TEMPO
Tetrahedrons
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Beschreibung
Zusammenfassung: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/NaClO2/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. [Display omitted]
ISSN:0040-4020
1464-5416
0040-4020
DOI:10.1016/j.tet.2012.03.066