Acyclic nucleoside bisphosphonates: Synthesis and properties of chiral 2-amino-4,6-bis[(phosphonomethoxy)alkoxy]pyrimidines

被引：32
作者：
Dolakova, Petra [1 ]
Dracinsky, Martin [1 ]
Masojidkova, Milena [1 ]
Solinova, Veronika [1 ]
Kasicka, Vaclav [1 ]
Holy, Antonin [1 ]
机构：
[1] Acad Sci Czech Republ, Inst Organ Chem & Biochem, CZ-16610 Prague 6, Czech Republic
来源：
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2009年 / 44卷 / 06期
关键词：
Acyclic nucleoside phosphonates; Pyrimidine; Bisphosphonates; Alkylation; ENANTIOMERIC N-(2-PHOSPHONOMETHOXYPROPYL) DERIVATIVES; SIMIAN IMMUNODEFICIENCY VIRUS; ANTIVIRAL ACTIVITY; IN-VITRO; PHOSPHONATE ANALOGS; NUCLEOTIDE ANALOGS; ADEFOVIR DIPIVOXIL; ANTITUMOR-ACTIVITY; PYRIMIDINE-BASES; PURINE;
D O I：
10.1016/j.ejmech.2008.09.031
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
2-Amino-4,6-bis[(phosphonomethoxy)alkoxy]pyrimidines bearing two equal or different achiral or chiral phosphonoalkoxy chains have been prepared either by aromatic nucleophilic substitution of 2-amino-4,6-dichloropyrimidine or by alkylation of 4,6-dihydroxy-2-(methylsulfanyl)pyrimidine with appropriate phosphonate-bearing building block. Alkylation of 4,6-dihydroxy-2-(methylsulfanyl)pyrimidine proved to be the method of choice for efficient preparation of variety of bisphosphonates. The enantiomeric purity of selected compounds was determined by capillary electrophoresis. Antiviral activity of bisphosphonates is discussed. (C) 2008 Elsevier Masson SAS. All rights reserved.
引用
收藏
页码：2408 / 2424
页数：17
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