糖苷合成研究ⅩⅣ2-烷氧基(2-苯硫基) 5-氟-3H-4-嘧啶酮木糖苷的合成及其抗肿瘤活性研究  

Studies on the Synthesis of Glycosides(XIV) The Synthesis of β D Xylopyranosides of 2 Alkoxy(2 Phenylthio) 5 Fluoro 3 H 4 Pyrimidone and Their Antitumor Activities

作　　者：孙昌俊[1] 戚聿新[1] 李爱霞 张华坤[2] 张建国[3] 

机构地区：[1]山东大学化学学院,济南250100 [2]山东大学生命科学院 [3]青岛海洋大学化学系,青岛266003

出　　处：《中国药物化学杂志》1999年第4期245-250,共6页Chinese Journal of Medicinal Chemistry

摘　　要：在相转移催化条件下,使2 ,3 ,4三O乙酰基1溴1脱氧αD木吡喃糖(1) 同2烷氧基(2苯硫基)5氟3 H4嘧啶酮(2a～2e) 反应,合成了2烷氧基(2苯硫基)3N(2 ,3 ,4三O乙酰基βD木吡喃糖1基)5氟4嘧啶酮(3a～3e) .(1) 与(2a～2e) 的银盐(4a ～4e) 在二甲苯中发生KoenigsKnorr 反应,合成了2烷氧基(2苯硫基)4O(2 ,3 ,4三O乙酰基βD木吡喃糖1基)5氟嘧啶(5a～5e) .化合物(3) 和(5) 的结构经红外光谱、核磁共振氢谱、质谱或元素分析所证实.初步的体外杀伤癌细胞试验表明。Alkoxy(2 phenylthio) 3 N (2,3,4 tri O acetyl β D xylopyranos 1 yl) 5 fluoro 4 pyrimidone(3a～3e)were synthesized by the condensation of 2,3,4 tri O acetyl 1 bromo 1 deoxy α D xylopyranose(1)with 2 alkoxy(2 phenylthio) 5 fluoro 3 H 4 pyrimidone(2a～2e)under phase transfer catalysis.2 Alkoxy(2 phenylthio) 4 O (2,3,4 tri O acetyl β D xylopyranos 1 yl) 5 fluoro pyrimidine(5a～5e)were obtained by the Koenigs Knorr reaction of (1) with the silver salts(4a～4e) of (2a～2e)in xylene.Ten new compounds with structure (3) and (5) were synthesized and their structures were confirmed by IR, 1H NMR,MS or elementary analysis.Preliminary results of the in vitro tests on KB,HCT 8 tumor cells showed that some of them were of certain antitumor activities.

关 键 词：氟脲嘧啶 相转移催化 糖苷 抗癌 

分 类 号：TQ463.54[化学工程—制药化工] R979.1[医药卫生—药品]