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

页码：2634 / 2646

页数：13

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