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有机化学
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有机化学 ›› 2011, Vol. 31 ›› Issue (06): 912-920. 上一篇    下一篇

研究简报

5,6-2H-1,2,4-三唑[3,4-b][1,3,4]噻二嗪衍生物的合成及抗癌活性

薛伟1,郑玉国2,郭晴晴3,卢平3,王贞超3,袁凯3   

  1. 1. 贵州大学
    2.
    3. 贵州大学精细化工研究开发中心
  • 收稿日期:2010-10-21 修回日期:2011-02-17 发布日期:2011-06-28
  • 通讯作者: 薛伟 E-mail:wxue@gzu.edu.cn

Synthesis and Antitumor Activity of 5,6-2H-[1,2,4]- triazolo [3,4-b][1,3,4]thiadiazine derivatives

  • Received:2010-10-21 Revised:2011-02-17 Published:2011-06-28

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取代苯甲醛与4-氨基-5-(3,4,5-三甲氧基苯基)-1,2,4-三唑-3-硫酮(2)缩合生成 5-(3,4,5-三甲氧基苯基)-4-取代苯基亚胺基-1,2,4-三唑-3-硫酮(3), 再烷基加成化为新型5,6-2H-1,2,4-三唑[3,4-b][1,3,4]噻二嗪衍生物(4). 化合物结构经1H NMR, 13C NMR, IR以及元素分析确认. 采用MTT法进行化合物抑制PC3癌细胞体外活性测试, 结果表明所合成的化合物具有不同程度的抑制PC3癌细胞活性, 其中化合物4a在10μmol?L-1浓度下对PC3的抑制率为75.9 %.

关键词: 没食子酸, 1,2,4-三唑[3,4-b][1,3,4]噻二嗪, 合成, 抗癌活性

A series of 4-(substituted-3-phenylideneamino)-3-(3,4,5-trimethoxyphenyl)- 1H-1,2,4-triazole-5(4H)-thione 3 were synthesized by condensation reaction of 4-amino-3-(3,4,5-trimethoxyphenyl)-1H-1,2,4-triazole-5(4H)-thione (2) with various substituted benzaldehydes. Alkylation of 3 with alkyl halides afforded [1,2,4]triazolo- [3,4-b][1,3,4]thiadiazine derivatives 4. Their structures were confirmed by 1H NMR, 13C NMR, IR and elemental analyses. Preliminary bioassay indicated that some compounds posed antitumor activity to PC3 cells in vitro by MTT method. The antiproliferation activity of compound 4a to PC3 cells at the concentration of 10 μmol?L-1 was 75.9 %.

Key words: Gallic acid, [1,2,4]triazolo[3,4-b][1,3,4]thiadiazine, Synthesis, Antitumor

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