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

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• 作者：Martin Maxmilian Kaiser ; Petr Jansa ; Martin Dra膷&iacute ; nský ; Zlatko Janeba ; ^{janeba@uochb.cas.cz} ; ^{zjaneba@yahoo.com}
• 关键词：Acyclic nucleoside phosphonates ; CPMEA ; HPMPA ; PMEA ; Oxidation ; TEMPO ; Microwave ; Antiviral
• 刊名：Tetrahedron
• 出版年：2012
• 期刊代码：107_00404020
• 类别：ch
• 出版时间：27 May, 2012
• 卷：68
• 期：21
• 页码：4003-4012
• 文件大小：1043 K

摘要

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鈥?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.