苷类化合物研究——Ⅳ.熊果苷类似物的合成

Studies on Glycosides——IV. Synthesis of Arbutin Analogs

熊果苷是从植物中分离到的一种成分,据报道具有低毒性镇咳、利尿、抗菌和尿道消毒作用等生物活性。由于熊果苷水溶性好,便于机体吸收,有希望成为临床的新型镇咳药,它的结构式如下式所示。为了研究构(包括端基异构)效(镇咳作用)关系,作者以熊果苷为模型化合物,对糖基和配糖体分别进行有限的修饰。

Arbutin analogs were synthesized by reacting 1-bromo-2, 3, 4, 6-tetra-O-acetyl- α-D-glucopyranose or galactopyranose with dihydroxybenzenes followed by mild hydro- lysis with methanolic ammonia. The anomeric configurations of these glycosides were assigned based on ~1H NMR and comparison of 1-C chemical shifts on the sugar moieties.