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![]() ![]() |
刊名 | CHEMISTRY & BIODIVERSITY
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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 |
DOI | 10.1002/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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