中国科学院机构知识库网格
Chinese Academy of Sciences Institutional Repositories Grid
Synthesis of (Glycopyranosyl-triazolyl)-purines and Their Inhibitory Activities against Protein Tyrosine Phosphatase 1B (PTP1B)

文献类型:期刊论文

作者Luo, Lei3,4; He, Xiao-Peng1,2; Shen, Qiang5; Li, Jing-Ya5; Shi, Xiao-Xin1; Xie, Juan2; Li, Jia5; Chen, Guo-Rong3,4
刊名CHEMISTRY & BIODIVERSITY
出版日期2011-11
卷号8期号:11页码:2035-2044
关键词Triazole Purines Inhibitors Protein tyrosine phosphatase
ISSN号1612-1872
DOI10.1002/cbdv.201000242
文献子类Article
英文摘要Development of novel purine derivatives has attracted considerable interest, since both purine and purine-based nucleosides display a wide range of crucial biological activities in nature. We report here a novel expansion of these studies by introducing gluco- or galactopyranosyl scaffold to the N- or 9-position (or both) of 6-Cl purine moiety via CuI-catalyzed Huisgen 1,3-dipolar cycloaddition. By such an efficient reaction, a series of glycosyl-triazolyl-purines were successfully synthesized in good yields. Biological evaluation showed that the majority of these glycoconjugates were good PTP1B inhibitors with IC50 values in low micromolar range (1.511.1 mu M). The benzylated sugar derivatives displayed better inhibitory potency than that of the acetylated ones. Replacement of Cl by MeO at C(6) of the purine moiety decreased the inhibition in the case of benzylated (glycosyl-mono-triazolyl)-purines 11 and 12 (IC50>80 mu M), whereas MeO-substituted benzylated bis[galactosyl-triazolyl]-purine 16 possessed the best inhibitory activity with an IC50 value of 1.5 mu M. Additionally, these compounds exhibited 2- to 57-fold selectivity over other PTPs (TCPTP, SHP1, SHP2, and LAR).
WOS关键词DISCOVERY ; PURINE ; DERIVATIVES ; NUCLEOSIDE ; CHEMISTRY ; TARGETS
资助项目National Natural Science Foundation of China[20876045] ; National Science & Technology Major Project of China 'Key New Drug Creation and Manufacturing Program'[2009ZX09302-001] ; Shanghai Science and Technology Community[10410702700] ; Shanghai Science and Technology Community[08DZ2291300] ; Shanghai Science and Technology Community[08QH14005] ; CNRS[00000000] ; ENS Cachan[00000000] ; French Embassy in China[00000000]
WOS研究方向Biochemistry & Molecular Biology ; Chemistry
语种英语
WOS记录号WOS:000297013200011
出版者WILEY-BLACKWELL
源URL[http://119.78.100.183/handle/2S10ELR8/278350]  
专题国家新药筛选中心
中科院受体结构与功能重点实验室
新药研究国家重点实验室
药物安全性评价中心
通讯作者Xie, Juan
作者单位1.E China Univ Sci & Technol, Sch Pharm, Dept Pharmaceut Engn, Shanghai 200237, Peoples R China;
2.ENS Cachan, PPSM, CNRS, F-94230 Cachan, France;
3.E China Univ Sci & Technol, Sch Chem & Mol Engn, Key Lab Adv Mat, Shanghai 200237, Peoples R China;
4.E China Univ Sci & Technol, Sch Chem & Mol Engn, Inst Fine Chem, Shanghai 200237, Peoples R China;
5.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Natl Ctr Drug Screening, Shanghai 201203, Peoples R China
推荐引用方式
GB/T 7714
Luo, Lei,He, Xiao-Peng,Shen, Qiang,et al. Synthesis of (Glycopyranosyl-triazolyl)-purines and Their Inhibitory Activities against Protein Tyrosine Phosphatase 1B (PTP1B)[J]. CHEMISTRY & BIODIVERSITY,2011,8(11):2035-2044.
APA Luo, Lei.,He, Xiao-Peng.,Shen, Qiang.,Li, Jing-Ya.,Shi, Xiao-Xin.,...&Chen, Guo-Rong.(2011).Synthesis of (Glycopyranosyl-triazolyl)-purines and Their Inhibitory Activities against Protein Tyrosine Phosphatase 1B (PTP1B).CHEMISTRY & BIODIVERSITY,8(11),2035-2044.
MLA Luo, Lei,et al."Synthesis of (Glycopyranosyl-triazolyl)-purines and Their Inhibitory Activities against Protein Tyrosine Phosphatase 1B (PTP1B)".CHEMISTRY & BIODIVERSITY 8.11(2011):2035-2044.

入库方式: OAI收割

来源:上海药物研究所

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