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

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-β-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/H2. 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.