目的:制备水杨酸糖酯,考察其刺激性和镇痛活性。方法:用羧酸有机碱法和羧酸盐直接反应2种方法制备水杨酸糖酯;用分步法合成乙酰水杨酸乙酰葡萄糖酯;用~1H-NMR和IR确认结构;用小鼠断尾法和扭体实验评价抗凝血活性和镇痛活性;用组织切片法观察刺激性。结果:合成了5个β-构型的水杨酸糖酯,其抗凝血活性和镇痛作用与阿司匹林相当;合成物的刺激性均小于原药和阿司匹林。结论:羧酸盐直接反应法制备水杨酸糖酯和分步法合成乙酰水杨酸糖酯为首次使用,该法简便易行,优于相转移催化法;水杨酸糖酯类修饰可以提高抗凝血作用和镇痛作用,降低刺激性。 OBJECTIVE: To prepare the sugar ester of salicylate and study its irritant and analgesic activity. Methods: Two kinds of methods were used to synthesize the sugar esters of salicylate with two methods, ie the carboxylic acid organic base and the carboxylate. The acetyl glucosyl acetylsalicylate was synthesized by the stepwise method. The structure was confirmed by ~ 1H-NMR and IR. The tail-end method and writhing test were used to evaluate anticoagulant activity and analgesic activity. Tissue sections were used to observe irritation. RESULTS: Five β-configuration salicylate esters were synthesized. Their anticoagulant activities and analgesic activities were comparable to those of aspirin. The irritation of the compounds was less than that of the original drug and aspirin. CONCLUSION: The preparation of sugar esters of salicylic acid by the direct reaction of carboxylates and the synthesis of sugar esters of acetylsalicylic acid by the stepwise method are the first time that this method is simple and convenient, which is better than the method of phase transfer catalysis. Improve anticoagulant effect and analgesic effect, reduce irritation.