Assembly and inhibitory activity of monovalent mannosides terminated with aromatic methyl esters: The effect of naphthyl groups

作者：Al Mughaid Hussein; Al Zoubi Raed M; Khazaaleh Maha; Grindley T Bruce

来源：Carbohydrate Research, 2017, 446: 76-84.

DOI：10.1016/j.carres.2017.03.020

• alpha-D-mannosides
• Click chemistry
• FimH
• Hemagglutination

A series of monovalent alpha-D-mannoside ligands terminated with aromatic methyl esters have been synthesized in excellent yields using the Cu(I) catalyzed azide-allcyne 1,3-dipolar cycloaddition ("click chemistry"). These mannosides were designed to have a unique aglycone moiety (tail) that combines a triazole ring attached to aromatic methyl esters via a six carbon alkyl chain. The mannose unit of these ligands was linked at the ortho, meta, and para positions of substituted methyl benzoates and 1-, 3-, and 6-substituted methyl 2-napthaoates. In hemagglutination assays, ligands (32A-38A) showed better inhibitory activities than the standard inhibitor, methyl alpha-D-mannopyranoside. Overall, the naphthylbased mannoside ligand (37A) showed the best activity and therefore merits further development.

• 出版日期2017-6-29