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一种新型的源自2-(膦酰基甲氧基)丙酸的无环核苷膦酸酯。

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

作者信息

Kaiser Martin Maxmilian, Jansa Petr, Dračínský Martin, Janeba Zlatko

机构信息

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, v.v.i., Flemingovo nám. 2, CZ-16610 Prague 6, Czech Republic.

出版信息

Tetrahedron. 2012 May 27;68(21):4003-4012. doi: 10.1016/j.tet.2012.03.066. Epub 2012 Mar 26.

DOI:10.1016/j.tet.2012.03.066
PMID:32287422
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7111817/
Abstract

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/NaClO oxidizing system. Although ()-3-(adenin-9-yl)-2-(phosphonomethoxy)propanoic acid (()-CPMEA) has been designed as a compound with potential anti-HIV activity, none of the newly prepared CPME analogues exhibited any antiviral activity.

摘要

已开发出一种便捷高效的合成方法，用于制备一类新型的、源自2-(膦酰基甲氧基)丙酸的无环核苷膦酸酯。该合成的关键步骤是使用TEMPO/NaClO/NaClO氧化体系，将3-羟基-2-(膦酰基甲氧基)丙基（HPMP）类似物优化氧化为相应的2'-羧基-PME（CPME）衍生物。尽管(-)-3-(腺嘌呤-9-基)-2-(膦酰基甲氧基)丙酸（(-)-CPMEA）被设计为一种具有潜在抗HIV活性的化合物，但新制备的CPME类似物均未表现出任何抗病毒活性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4bc/7111817/00ed02c2b24e/gr1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4bc/7111817/00ed02c2b24e/gr1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d4bc/7111817/00ed02c2b24e/gr1.jpg

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GS-9219--a novel acyclic nucleotide analogue with potent antineoplastic activity in dogs with spontaneous non-Hodgkin's lymphoma.
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