Department of Chemistry, Indian Institute of Technology (BHU), Varanasi, Uttar Pradesh, 221005, India.
Department of Pharmaceutical Engineering & Technology, Indian Institute of Technology (Banaras Hindu University), Varanasi, 221005, India.
Carbohydr Res. 2023 Oct;532:108920. doi: 10.1016/j.carres.2023.108920. Epub 2023 Aug 4.
Cinnamic acid-containing sugar compounds such as phenylethanoid glycosides are widely present in nature and display various biological activities. In this work, the synthesis of trans-cinnamic acid containing phenylethanoid glycosides was achieved via palladium-catalyzed cross-coupling reactions between glycosyl acrylic esters and aryldiazonium salts. A wide range of functionalized aryldiazonium salts were successfully coupled with 6-O- and 4-O-acrylic esters of glucose under optimized conditions. The reactions proceeded at room temperature in the absence of additives and base. The desired products were obtained in good to excellent yields. Selected compounds from the library were screened for anti-Alzheimer activity, while compound 16 displayed significant inhibitory activities against butyrylcholinesterase (BChE) and acetylcholinesterase (AChE) enzymes.
含肉桂酸的糖化合物，如苯乙醇苷类，广泛存在于自然界中，并表现出多种生物活性。在这项工作中，通过钯催化的糖基丙烯酯和芳基重氮盐之间的交叉偶联反应，实现了含反式肉桂酸的苯乙醇苷的合成。在优化条件下，各种功能化的芳基重氮盐与葡萄糖的 6-O-和 4-O-丙烯酯成功偶联。反应在室温下进行，无需添加剂和碱。在良好到优秀的产率下得到了所需的产物。从文库中筛选了一些化合物进行抗阿尔茨海默病活性测试，其中化合物 16 对丁酰胆碱酯酶（BChE）和乙酰胆碱酯酶（AChE）表现出显著的抑制活性。
