化学学报 ›› 1956, Vol. 22 ›› Issue (3): 163-170. 上一篇    下一篇

有机化学

血吸蟲病化學治療的研究 Ⅰ.2-氨基葡萄糖的幾種新衍生物的合成

嵇汝運   

  1. 中国科学院药物研究所
  • 投稿日期:1956-01-28 发布日期:2013-06-04

CHEMOTHERAPEUTIC STUDIES ON SCHISTOSOMIASIS Ⅰ.THE SYNTHESIS OF SOME NEW GLUCOSAMINE DERIVATIVES

KYI ZU-YOONG   

  1. Institute of Materia Medica, Academia Sinica, Shanghai
  • Received:1956-01-28 Published:2013-06-04

2-苯甲碳醯-2-去羥-D-陆圜葡萄糖α-甲基甙(Ⅰ)与苯甲醛縮合后形成了結晶的4,6-苯次甲基衍生物(Ⅱ),醯化後分別變為3-乙醯,3-苯甲醯及3-甲磺醯三個衍生物(Ⅲa,b,c)。苯次甲基脫去後未能獲得結晶的4,6-二羟基化合物。2-苯甲醯氨基-2-去羥-D-陸圜葡萄糖α-甲基甙(Ⅴ)經三苯甲基化後再醯化,分別獲得了3,4-二乙醯-2-苯甲醯氨基2-去羥-6-三苯甲基-D-陸圜葡萄糖甙(Ⅵa)及其相應的3,4-二苯甲酸酯(Ⅵb);前者脫去三苯甲基後轉變為6-羥基化合物(Ⅶ)。C6上的游離羥基是將這第一羥基氧化后從陽性的醛酸顏色反應證明的。2-苯甲碳醯-2-去羥-D-陆圜葡萄糖α-甲基甙(Ⅰ)与一分子的甲苯磺醯氯成為相應的6-磺酸酯(Ⅸ),後者的構造從它与碘化鈉變為碘化物(Ⅹ)的反應證明。

It was recently reported[1] that elucosamine (2-amino-2-deoxy-D-glucopyranose) reduced the rate of glycolysis of scbisiosoma mansoni and its G-phosphate inhibited the glucokinase action of the parasite, and that the reduction of the survival of the parasite by glucosamine was observed both in vitro and n vivo. Some new glucosamine derivatives, which may serve as potential intermediates for the preparation of chemotherapeutic agents against schistosomiasis, have there fore been synthesized.