文献类型：期刊文献

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

作者：Song, Shao-Xing[1,2];Zhang, Hai-Lin[1,2];Kim, Chol-Guk[1,2];Sheng, Li[3];He, Xiao-Peng[4,5];Long, Yi-Tao[1,2];Li, Jia[3];Chen, Guo-Rong[1,2]

机构：[1]E China Univ Sci & Technol, Sch Chem & Mol Engn, Key Lab Adv Mat, Shanghai 200237, Peoples R China;[2]E China Univ Sci & Technol, Sch Chem & Mol Engn, Inst Fine Chem, Shanghai 200237, Peoples R China;[3]Chinese Acad Sci, Shanghai Inst Mat Med, Natl Ctr Drug Screening, Shanghai 201203, Peoples R China;[4]E China Univ Sci & Technol, Sch Pharm, Dept Pharmaceut Engn, Shanghai 200237, Peoples R China;[5]ENS Cachan, CNRS, PPSM, F-94230 Cachan, France

年份：2010

卷号：66

期号：52

起止页码：9974

外文期刊名：TETRAHEDRON

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000285727500025)】；

基金：This project was supported by National Natural Science Foundation of China (Grant No. 20876045), National Science & Technology Major Project of China 'Key New Drug Creation and Manufacturing Program' (No. 2009ZX09302-001), Shanghai Science and Technology Community (No.10410702700, 08DZ2291300 and 09DZ2291200), and Chinese Academy of Sciences (No. KSCX2-YW-R-168). X.-P. He also gratefully acknowledges the French Embassy for the financial support of a co-tutored doctoral program as well as his French advisor Prof. J. Xie (ENS Cachan).

语种：英文

外文关键词：Glycolipid derivatives; Microwave-assisted click chemistry; EIS measurement; Gold surface adsorption; Cytotoxicity

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.