Synthesis of (±)-1,2,3-triazolo-3′-deoxy-4′-hydroxymethyl carbanucleosides via 'click' cycloaddition
Synthesis of (±)-1,2,3-triazolo-3′-deoxy-4′-hydroxymethyl carbanucleosides via 'click' cycloaddition
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DOI：
10.1016/j.tet.2008.11.065
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发表时间：
2009-02-07
期刊：
影响因子：
2.1
通讯作者：
Agrofoglio, Luigi A.
中科院分区：
文献类型：
--
作者：
Broggi, Julie;Joubert, Nicolas;Agrofoglio, Luigi A.
研究了不同反应条件和对杂环基团进行不同调控的1，2，3-三唑-3 '-脱氧-4'-羟甲基碳核苷的合成方法。通过亲核取代或通过1，3-偶极Huisgen环加成，在假糖上有效地引入杂环部分。用后一种方法，从相应的叠氮基碳环和各种末端或内部炔制备1，4-二取代和1，4，5-三取代-（+/-）-[1，2，3]-三唑并-3 ′-脱氧-4 ′-羟甲基碳核苷。最终化合物的抗病毒活性和细胞毒性作为天花抑制剂进行了评价。不幸的是，在浓度达到100 mM时，它们都不能抑制vero细胞中牛痘病毒（Lister株）或牛痘病毒（Brighton株）的产生。(C)2008爱思唯尔有限公司保留所有权利。
The synthesis of 1,2,3-triazolo-3'-deoxy-4'-hydroxymethyl carbanucleosides with different reaction conditions and diverse modulations on the heterocycle residues was developed. Heterocycle moieties were efficiently introduced on the pseudo-sugar either via nucleophilic substitution or via 1,3-dipolar Huisgen cycloaddition. With this latter approach, 1,4-disubstituted and 1,4,5-trisubstituted-(+/-)-[1,2,3]-triazolo-3'-deoxy-4'-hydroxymethyl carbanucleosides were prepared from the corresponding azido-carbocycle and various terminal or internal alkynes. Antiviral activities and cellular toxicities of the final compounds were evaluated as smallpox inhibitors. Unfortunately, at concentrations tip to 100 mM, none of them inhibited production of vaccinia virus (Lister strain) or cowpox Virus (Brighton strain) in vero cells. (C) 2008 Elsevier Ltd. All rights reserved.