A concise synthesis of N-substituted fagomine derivatives and the systematic exploration of their alpha-glycosidase inhibition
文献类型：期刊论文
| 作者 | Jiang, Fu-xiang1; Liu, Qiao-zhen1; Zhao, Dan2; Luo, Cui-ting1; Guo, Cui-ping1; Ye, Wen-cai1,3; Luo, Cheng2 ; Chen, Heru1,2,3
|
| 刊名 | EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
 |
| 出版日期 | 2014-04 |
| 卷号 | 77页码:211-222 |
| 关键词 | Azasugars Fagomine alpha-glycosidase Total synthesis Molecular docking |
| ISSN号 | 0223-5234 |
| DOI | 10.1016/j.ejmech.2014.03.004 |
| 文献子类 | Article |
| 英文摘要 | A novel and concise scheme has been developed successfully for the syntheses of N-substituted fagomine derivatives. The transformation of lactone (2) to 1,5-diol (3) was carried on with high yield (93-95%). The cyclization of 4 to 5 is a high stereoselective reaction (de value > 98%). It is disclosed that bulky substituent at N atom of the piperidine decreases the inhibition activity except those substituents having the ability of salvation or forming disulfide bond with M444 at the active site of alpha-glycosidase, which enhance the interaction with enzyme. Compounds with S-configuration at C-3 show greater activity than those with R-configuration. The structure activity relationship study is also supported by molecular docking analysis. (C) 2014 Elsevier Masson SAS. All rights reserved. |
| WOS关键词 | TYPE-2 DIABETES-MELLITUS ; GLYCOGEN-PHOSPHORYLASE ; AGENTS ; GLUCOSIDASE ; SECRETION |
| 资助项目 | Guangdong Provincial Project of Science and Technology[2010A030100006] ; State Key Laboratory of Drug Research[SIMM1302KF-12] ; State Key Laboratory of Drug Research[1004KF-15] ; National Natural Science Foundation of China[81172982] ; 863 program[2012AA020302] |
| WOS研究方向 | Pharmacology & Pharmacy |
| 语种 | 英语 |
| WOS记录号 | WOS:000335874800024 |
| 出版者 | ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/277124]  |
| 专题 | 新药研究国家重点实验室 中科院受体结构与功能重点实验室 |
| 通讯作者 | Chen, Heru |
| 作者单位 | 1.Jinan Univ, Coll Pharm, Inst Tradit Chinese Med & Nat Prod, Guangzhou 510632, Guangdong, Peoples R China; 2.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China; 3.Jinan Univ, Guangdong Prov Key Lab Pharmacodynam Constituents, Guangzhou 510632, Guangdong, Peoples R China |
| 推荐引用方式 GB/T 7714 | Jiang, Fu-xiang,Liu, Qiao-zhen,Zhao, Dan,et al. A concise synthesis of N-substituted fagomine derivatives and the systematic exploration of their alpha-glycosidase inhibition[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY,2014,77:211-222. |
| APA | Jiang, Fu-xiang.,Liu, Qiao-zhen.,Zhao, Dan.,Luo, Cui-ting.,Guo, Cui-ping.,...&Chen, Heru.(2014).A concise synthesis of N-substituted fagomine derivatives and the systematic exploration of their alpha-glycosidase inhibition.EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY,77,211-222. |
| MLA | Jiang, Fu-xiang,et al."A concise synthesis of N-substituted fagomine derivatives and the systematic exploration of their alpha-glycosidase inhibition".EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY 77(2014):211-222. |
入库方式： OAI收割
来源：上海药物研究所
浏览0
下载0
收藏0
其他版本
除非特别说明，本系统中所有内容都受版权保护，并保留所有权利。