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Expeditious preparation of triazole-linked glycolipids via microwave accelerated click chemistry and their electrochemical and biological assessments

文献类型：期刊论文

作者Song, Shao-Xing1,4; Zhang, Hai-Lin1,4; Kim, Chol-Guk1,4; Sheng, Li5; He, Xiao-Peng2,3; Long, Yi-Tao1,4; Li, Jia5; Chen, Guo-Rong1,4
刊名TETRAHEDRON
出版日期2010-12-24
卷号66期号:52页码:9974-9980
关键词Glycolipid derivatives Microwave-assisted click chemistry EIS measurement Gold surface adsorption Cytotoxicity
ISSN号0040-4020
DOI10.1016/j.tet.2010.10.033
文献子类Article
英文摘要A series of triazole-linked ester-type glycolipids were efficiently prepared via a two-step sequence involving microwave accelerated 'click' chemistry and debenzylation. All carbon chain length varied O-alkynyl fatty esters used to couple with 1-azido-tetra-O-benzyl-beta-D-glucoside showed excellent tolerance to the microwave-assisted 1,3-dipolar cycloaddition (click reaction), forming the unique cycloadducts in almost quantitative yields of 92.9-99.0% within a quarter. The desired glycolipids were then readily afforded via the successive hydrogenolysis promoted by PdCl2/H-2. Their adsorption competence on gold electrode were evaluated through EIS (electrochemical impedance spectroscopy) measurement and the resulting structure-activity relationship (SAR) was discussed. In addition, the cytotoxicity of this triazolyl glycolipid class on HeLa (cervix cancer) cell line was identified by MTT assay. (C) 2010 Elsevier Ltd. All rights reserved.
WOS关键词WELL STEEL N-80 ; CORROSION-INHIBITORS ; MILD-STEEL ; HYDROCHLORIC-ACID ; DERIVATIVES ; POTENT ; AZIDES ; MEDIA
资助项目National Natural Science Foundation of China[20876045] ; 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[09DZ2291200] ; Chinese Academy of Sciences[KSCX2-YW-R-168] ; French Embassy[00000000]
WOS研究方向Chemistry
语种英语
WOS记录号WOS:000285727500025
出版者PERGAMON-ELSEVIER SCIENCE LTD
源URL[http://119.78.100.183/handle/2S10ELR8/278684]  
专题国家新药筛选中心
药物安全性评价中心
通讯作者He, Xiao-Peng
作者单位1.E China Univ Sci & Technol, Sch Chem & Mol Engn, Inst Fine Chem, Shanghai 200237, Peoples R China;
2.ENS Cachan, CNRS, PPSM, F-94230 Cachan, France
3.E China Univ Sci & Technol, Sch Pharm, Dept Pharmaceut Engn, Shanghai 200237, Peoples R China;
4.E China Univ Sci & Technol, Sch Chem & Mol Engn, Key Lab Adv Mat, Shanghai 200237, Peoples R China;
5.Chinese Acad Sci, Shanghai Inst Mat Med, Natl Ctr Drug Screening, Shanghai 201203, Peoples R China;
推荐引用方式
GB/T 7714		 Song, Shao-Xing,Zhang, Hai-Lin,Kim, Chol-Guk,et al. Expeditious preparation of triazole-linked glycolipids via microwave accelerated click chemistry and their electrochemical and biological assessments[J]. TETRAHEDRON,2010,66(52):9974-9980.
APA Song, Shao-Xing.,Zhang, Hai-Lin.,Kim, Chol-Guk.,Sheng, Li.,He, Xiao-Peng.,...&Chen, Guo-Rong.(2010).Expeditious preparation of triazole-linked glycolipids via microwave accelerated click chemistry and their electrochemical and biological assessments.TETRAHEDRON,66(52),9974-9980.
MLA Song, Shao-Xing,et al."Expeditious preparation of triazole-linked glycolipids via microwave accelerated click chemistry and their electrochemical and biological assessments".TETRAHEDRON 66.52(2010):9974-9980.

入库方式： OAI收割

来源：上海药物研究所

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