Assembly and inhibitory activity of monovalent mannosides terminated with aromatic methyl esters: The effect of naphthyl groups
作者:Hussein Al-Mughaid、Raed M. Al-Zoubi、Maha Khazaaleh、T. Bruce Grindley
DOI:10.1016/j.carres.2017.03.020
日期:2017.6
A series of monovalent α-D-mannoside ligands terminated with aromatic methyl esters have been synthesized in excellent yields using the Cu(I) catalyzed azide-alkyne 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
使用Cu(I)催化的叠氮化物-炔烃1,3-偶极环加成反应(“点击化学”),已以优异的产率合成了一系列以芳香族甲基酯为末端的单价α-D-甘露糖苷配体。这些甘露糖苷被设计成具有独特的糖苷配基部分(尾部),该糖苷配基结合了通过六碳烷基链连接到芳族甲基酯上的三唑环。这些配体的甘露糖单元在取代的苯甲酸甲酯和1-,3-和6-取代的2-萘甲酸甲酯的邻位,间位和对位连接。在血凝测定中,配体(32A-38A)显示出比标准抑制剂甲基α-D-甘露吡喃糖苷更好的抑制活性。总体而言,基于萘基的甘露糖苷配体(37A)表现出最佳的活性,因此值得进一步发展。