cIDPRE及其类似物的微波辅助合成优化

doi:10.5246/jcps.2011.06.071

cIDPRE及其类似物的微波辅助合成优化

刘剑, 杨振军, 张亮仁^*, 张礼和

北京大学医学部天然药物及仿生药物国家重点实验室, 北京 100191

收稿日期:2011-05-20 修回日期:2011-09-20 出版日期:2011-11-15 发布日期:2011-11-15
通讯作者: 张亮仁*

Optimization of microwave-assisted synthesis of N¹-ethoxymethyl-substituted cyclic inosine diphosphoribose and its analogues

Jian Liu, Zhen-Jun Yang, Liang-Ren Zhang^*, Li-He Zhang

State Key Laboratory of Natural and Biomimetic Drugs, Peking University Health Science Center, Beijing 100191, China

Received:2011-05-20 Revised:2011-09-20 Online:2011-11-15 Published:2011-11-15
Contact: Liang-Ren Zhang*

摘要/Abstract

摘要：

本文发展了采用一种微波辅助分子内环合制备环腺苷二磷酸核糖 (cADPR)类似物-N¹-乙氧基甲基-环肌苷二磷酸核糖 (cIDPRE) 的新合成工艺。新合成路线以异亚丙基保护的肌苷为起始原料, 经取代、磷酸化、微波辅助分子内环合及异亚丙基脱除得到目标化合物, 改进后的合成工艺路线短, 效率高。微波辅助分子内环合方法同时适合8-NH2, 8-Br取代的cIDPRE衍生物的合成。

关键词: cADPR, cIDPRE, 化学合成, 微波辅助合成

Abstract:

An optimized approach for the synthesis of N¹-ethoxymethyl-substituted cyclic inosine diphosphoribose (cIDPRE), an analogue of cyclic adenosine diphosphoribose (cADPR), has been developed via microwave-assisted intramolecular cyclization. The target compound has been successfully obtained through N¹-substitution, phosphorylation, cyclization and deprotection. By using this method, 8-amino and bromo-substituted cIDPRE analogues were successfully obtained in good yield. The new approach has greatly shortened the synthetic route and enhanced the overall efficiency.

Key words: cADPR, cIDPRE, Chemical synthesis, Microwave-assisted synthesis

中图分类号:

R916

Supporting:

Foundation items: National Natural Science Foundation of China (Grant No. 20910094) and Ministry of Education of China (Grant No. 200800010078).
^*Corresponding author. Tel.: 86-10-82802567

刘剑, 杨振军, 张亮仁^*, 张礼和. cIDPRE及其类似物的微波辅助合成优化[J]. , DOI: 10.5246/jcps.2011.06.071.

Jian Liu, Zhen-Jun Yang, Liang-Ren Zhang^*, Li-He Zhang. Optimization of microwave-assisted synthesis of N¹-ethoxymethyl-substituted cyclic inosine diphosphoribose and its analogues[J]. , DOI: 10.5246/jcps.2011.06.071.

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