O-(1-芳硒基-3-叠氮基)异丙基-O-2-(N^3-替加氟)烷基硫代磷酯的合成与活性  

Synthesis and Antitumor of O-(1-Arylseleno-3-azido)isopropyl-O-2-(N_3-tegafur)alkyl Thiophosphate

作　　者：刘文奇[1] 尹显洪[2] 臧中林[3] 余晓芬[4] 陶李明[1] 李言杰[3] 许新华[3] 

机构地区：[1]湘南学院化学系,郴州423000 [2]广西民族大学化学与生态工程学院,南宁530006 [3]湖南大学化学化工学院,长沙410082 [4]湖南学院基础医学部,郴州423000

出　　处：《有机化学》2009年第12期2021-2025,共5页Chinese Journal of Organic Chemistry

基　　金：湖南省自然科学基金(No.08jj3018);国家自然科学基金(No.20372020)资助项目

摘　　要：以碘作催化剂,无水苯为溶剂,六乙基亚磷酰三胺依次与羟乙基替加氟、1-芳硒基甘油及硫反应,得中间体硒代环甘油磷脂替加氟缀合物2a～2f.以无水N,N-二甲基甲酰胺(DMF)作溶剂,室温下,叠氮化钠中对2a～2f进行亲核开环,得到O-(1-芳硒基-3-叠氮基)异丙基-O-2-(N3-替加氟)乙基硫代磷酯.体外活性测试结果表明,目标化合物3a～3f对膀胱癌细胞PGA1抑制作用比替加氟高,对胃癌细胞BGC-823的抑制作用与替加氟相当.The intermediates 2a-2f of cyclic （l-arylseleno）glycerol phosphate and tegafur conjugates were synthesized by one-pot reaction of hexaethyl phosphorous triamide, activated by a catalytic amount of iodine, with （N^3-tegafur）alkanol, 1-arylselenoglycerol and sulphur successively in refluxing benzene. O-（1-Arylseleno-3-azido）isopropyl-O-2-（N3-tegafur）alkyl thiophosphate （3a-3f） were obtained via nucleophilic ring-opening of sodium azide to 2a-2f in dry DMF at room temperature, and their antitumor activities were tested. The results showed that their antimutor activities were higher than tegafur against human urinary bladder cancer cell PGA1, and equivalent to tegafur against BGC-823.

关 键 词：替加氟 有机硒 叠氮化钠 磷酸酯 抗癌活性 

分 类 号：TQ460.1[化学工程—制药化工]