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4-取代三唑基核苷的高效合成及其体外细胞抑制活性

Efficient synthesis and in vitro cytostatic activity of 4-substituted triazolyl-nucleosides.

作者信息

El Akri Khalid, Bougrin Khalid, Balzarini Jan, Faraj Abdesslem, Benhida Rachid

机构信息

Laboratoire de Chimie des Molécules Bioactives et des Arômes, UMR-CNRS 6001, Institut de Chimie de Nice, Université de Nice-Sophia Antipolis, Parc Valrose, F-06108 Nice Cédex 2, France.

出版信息

Bioorg Med Chem Lett. 2007 Dec 1;17(23):6656-9. doi: 10.1016/j.bmcl.2007.08.077. Epub 2007 Sep 29.

Abstract

We report herein an efficient synthesis of 4-substituted triazolyl-nucleosides and their in vitro cytostatic activity. The synthesis is based on a straightforward 1,3-dipolar cycloaddition between 1-azido-ribose 2 and terminal alkynes under a cooperative effect of microwave activation and copper (I) catalysis. All cycloadducts were obtained in nearly quantitative yield after a short reaction time (1 to 2min). After removal of acetyl protecting groups, the free nucleosides were evaluated against L1210, Molt4/C8, and CEM tumor cell lines. Structure-activity relationship study shows that the substituent on the triazole ring has a major effect since nucleosides 4c and 4g, containing, respectively, a long alkyl chain and an aryl donor group are the most active compounds in this series.

摘要

我们在此报告4-取代三唑基核苷的高效合成及其体外细胞生长抑制活性。该合成基于在微波活化和铜(I)催化的协同作用下,1-叠氮核糖2与末端炔烃之间直接进行的1,3-偶极环加成反应。在短反应时间(1至2分钟)后,所有环加成产物均以几乎定量的产率获得。除去乙酰保护基后,对游离核苷针对L1210、Molt4/C8和CEM肿瘤细胞系进行评估。构效关系研究表明,三唑环上的取代基具有主要影响,因为分别含有长烷基链和芳基供体基团的核苷4c和4g是该系列中活性最高的化合物。

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