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有机化学
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有机化学 ›› 2009, Vol. 29 ›› Issue (12): 2021-2025. 上一篇    下一篇

研究简报

O-(1-芳硒基-3-叠氮基)异丙基- O-2-(N3-替加氟)烷基硫代磷酯的合成与活性

刘文奇*,a；尹显洪b；臧中林c；余晓芬d；陶李明a；李言杰c；许新华*,c   

  1. (a湘南学院化学系 郴州 423000)
     (b广西民族大学化学与生态工程学院 南宁 530006)
     (c湖南大学化学化工学院 长沙 410082) 
    (d湘南学院基础医学部 郴州 423000)
  • 收稿日期:2009-02-10 修回日期:2009-06-14 发布日期:2009-07-23
  • 通讯作者: 许新华 E-mail:xhx1581@21cn.com, xhx1581@yahoo.com.cn
  • 基金资助:

    国家级.国家自然科学基金

The Synthesis and Antitumor Activity of O-（1-arylseleno-3-azido）isopropyl-O-2-(N3- tegafur)alkyl thiophosphate

Liu, Wenqi*,a；Yin, Xianhongb；Zang, Zhonglinc；Yu, Xiaofend； Tao, Liminga；Li, Yanjiec；Xu, Xinhua*,c   

  1. (a Department of Chemistry, Xiangnan University, Chenzhou 423000) 
    (b College of Chemistry and Ecological Engineering, Guangxi University for Nationalities, Nanning) 
    (c College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082)
     (d Department of Basic Medicine, Xiangnan University, Chenzhou 423000)
  • Received:2009-02-10 Revised:2009-06-14 Published:2009-07-23

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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.

关键词: 替加氟, 有机硒, 叠氮化钠, 磷酸酯, 抗癌活性

The intermediates 2a～2f of cyclic (1-arylseleno)glycerol phosphate and tegafur conjugates were synthesized by one-pot reaction of hexaethyl phosphorous triamide, activated by a catalytic amount of iodine, with (N3-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 nu-cleophilic 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.

Key words: tegafur, organic selenium, sodium azide, phosphate, antitumor activity