有机化学 ›› 1992, Vol. 12 ›› Issue (3): 273-277. 上一篇    下一篇

研究论文

5-氟脲嘧啶的β-D-半乳吡喃糖苷的合成

孙昌俊;陈再成;张以宁;王义贵;张成如   

  1. 山东大学化学系
  • 发布日期:1992-06-25

Synthesis of galactopyranosides of 5-fluorouracil

SUN CHANGJUN;CHEN ZAICHENG;ZHANG YINING;WANG YIGUI;ZHANG CHENGRU   

  • Published:1992-06-25

5-氟脲嘧及其衍生物是目前临床上广泛使用的抗代谢类抗癌药物, 主要适用于消化道癌、乳腺癌、肺癌等, 但具有一定的毒性, 主要表现为骨髓抑制和胃肠道反应。我们以Koenigs-Knorr法和相转催化法合成了5-氟脲嘧啶的两种类型(-N型, -O型)的半乳吡喃糖苷。这些糖苷类化合物在体内糖苷的作用下, 有可能缓慢地分解释放出5-氟脲嘧啶, 降低其毒性, 提高抑瘤效果。

关键词: 半乳糖, 山东省自然科学基金, 氟脲嘧啶, 糖苷, 抗癌药, 相转移催化, 吡喃糖

Two acetyl galactopyranosides 2-O-benzyl-4-O-(2',3',4',6'-tetra-O-acetyl-b-D-galactopyranosyl)-5-fluoro uracil (I) and 2-O-benzyl-3-N-(2',3',4',6'-tetra-O-acetyl-b-D-galactopyranosyl)-5-fluoro uracil (II) were synthesized by the reaction of 2-O-benzyl-5-fluorouracil and a-acetobromogalactose (III). Under phase transfer catalysis I was also synthesized by the reaction of silver salt of 2-O-benzyl-5-fluorouracil and III. I and II were treated with ammonia in MeOH to obtain deacetylated galactopyranosides, which were hydrogenated in the presence of 10% Pd-C catalyst to obtain galactopyranosides of 5-fluorouracil, IV and V resp.

Key words: FLUOROURACILUM, ANTICARCINOGEN, GALACTOSE, PYRANOSE, GLYCOSIDE, PHASE TRANSFER CATALYSIS

中图分类号: