简洁合成有潜在糖苷酶抑制活性的氧桥双环氮杂糖和硫杂糖

简洁合成有潜在糖苷酶抑制活性的氧桥双环氮杂糖和硫杂糖

孟祥豹, 李妍萍, 李中军^*

北京大学药学院化学生物学系天然药物与仿生药物国家重点实验室, 北京 100083

收稿日期:2007-12-12 修回日期:2007-02-10 出版日期:2007-03-15 发布日期:2007-03-15
通讯作者: 李中军*

Concise synthesis of oxy-bridged bicyclic azasugar and thiosugar as potential glycosidase inhibitors

Xiang-Bao Meng, Yan-Ping Li, Zhong-Jun Li^*

Department of Chemical Biology, School of Pharmaceutical Sciences, State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100083, China

Received:2007-12-12 Revised:2007-02-10 Online:2007-03-15 Published:2007-03-15
Contact: Zhong-Jun Li*

摘要/Abstract

摘要：

目的发展一种简洁合成具有新型骨架的双环氮杂糖和硫杂糖的新方法。方法化合物1的两个伯羟基先在吡啶中用对甲苯磺酰氯保护, 接下来用硫化钠和伯胺关环高收率地生成氧桥双环分子。结果经几步反应成功地从L-山梨糖合成了三种双环氮杂糖和硫杂糖。结论本方法提供了一种合成具有潜在糖苷酶抑制活性的氧桥双环氮杂糖和硫杂糖的有效途径。

关键词: 氧桥, 氧桥, 氧桥, 双环氮杂糖, 双环氮杂糖, 双环氮杂糖, 双环硫杂糖, 双环硫杂糖, 双环硫杂糖, 关环反应, 关环反应, 关环反应

Abstract:

Aim To develop a concise method for the synthesis of bicyclic azasugar and thiosugar with novel scaffold. Methods The two primary hydroxyl groups of compound 1 were selectively protected with tosyl cloloride in pyridine, followed by ring-closure with sodium sulfide or primary amine to form the oxy-bridged bicyclic molecules in good yields. Results Two bicyclic azasugars and a thiosugar were produced from L-sorbose in several steps. Conclusion The described procedures provide an efficient method to synthesize bicyclic azasugar and thiosugar with novel scaffold as potential glycosidase inhibitors.

Key words: Oxy-bridge, Oxy-bridge, Bicyclic azasugar, Bicyclic azasugar, Bicyclic thiosugar, Bicyclic thiosugar, Ring-closure, Ring-closure

中图分类号:

R916.41

Supporting:

^*Corresponding author. Tel.: 86-10-82801714

孟祥豹, 李妍萍, 李中军^*. 简洁合成有潜在糖苷酶抑制活性的氧桥双环氮杂糖和硫杂糖[J]. .

Xiang-Bao Meng, Yan-Ping Li, Zhong-Jun Li^*. Concise synthesis of oxy-bridged bicyclic azasugar and thiosugar as potential glycosidase inhibitors[J]. .

参考文献

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