Synthesis of 3′-O-phosphonomethyl nucleosides with an adenine base moiety

被引：32
|
作者：
Vina, Dolores
Wu, Tongfei
Renders, Marleen
Laflamme, Genevieve
Herdewijn, Piet
机构：
[1] Katholieke Univ Leuven, Med Chem Lab, Rega Inst Med Res, B-3000 Louvain, Belgium
[2] Gilead Sci Inc, Foster City, CA 94404 USA
来源：
TETRAHEDRON | 2007年 / 63卷 / 12期
关键词：
nucleosides; phosphonates; HIV; threose; erythrose;
D O I：
10.1016/j.tet.2007.01.032
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A synthetic scheme has been developed for the synthesis of 2'-deoxythreose phosphonate nucleosides from beta-hydroxy-gamma-butyrolactone and of 2'-azido erythrose phosphonate nucleosides from dihydroxydihydrofuran-1-one. In addition several a-L-arabinofuranose phosphonate nucleosides were synthesized starting from protected a-D-galactofuranose. Unfortunately, none of the synthesized compounds show activity in an HIV-1 assay. One of these compounds, a locked phosphonate nucleoside, was evaluated (as diphosphate) for its potential to be incorporated into DNA using HIV-1 reverse transcriptase. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2634 / 2646
页数：13
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