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

被引：10
作者：
Kaiser, Martin Maxmilian [1 ]
Jansa, Petr [1 ]
Dracinsky, Martin [1 ]
Janeba, Zlatko [1 ]
机构：
[1] Acad Sci Czech Republ, Inst Organ Chem & Biochem, Vvi, CZ-16610 Prague 6, Czech Republic
来源：
TETRAHEDRON | 2012年 / 68卷 / 21期
关键词：
Acyclic nucleoside phosphonates; CPMEA; HPMPA; PMEA; Oxidation; TEMPO; Microwave; Antiviral; L-HOMOCYSTEINE HYDROLASE; ANTIVIRAL ACTIVITY; DNA VIRUS; N-6-SUBSTITUTED ADENINES; NUCLEOTIDE ANALOGS; RUTHENIUM TETRAOXIDE; CYTOSTATIC ACTIVITY; IN-VITRO; DERIVATIVES; OXIDATION;
D O I：
10.1016/j.tet.2012.03.066
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
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'-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. (C) 2012 Elsevier Ltd. All rights reserved.
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收藏
页码：4003 / 4012
页数：10
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