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有机化学
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有机化学 ›› 2010, Vol. 30 ›› Issue (07): 1093-1097. 上一篇    下一篇

研究简报

4-(1,3,4-噻二唑-2-巯基)苯并[4,5]呋喃[3,2-d]嘧啶类衍生物合成、晶体结构及抗癌活性

赵云，欧阳贵平*，徐维明，金林红，袁凯   

  1. (贵州大学精细化工研究开发中心 教育部绿色农药与农业生物工程重点实验室 贵阳 550025)
  • 收稿日期:2010-01-06 修回日期:2010-03-18 发布日期:2010-04-19
  • 通讯作者: 赵云 E-mail:zhaolee007@163.com

Synthesis, X-ray Structure and Antitumor Activity of 4-(1,3,4- Thiadiazole-2-ylthio)benzo[4,5]furo[3,2-d]pyrimidine Derivatives

ZHAO Yun, OUYang Gui-Ping , XU Wei-Ming, JIN Lin-Hong, YUAN Kai   

  1. (Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Research and Development Center of Fine Chemicals, Guizhou University, Guiyang 550025)
  • Received:2010-01-06 Revised:2010-03-18 Published:2010-04-19
  • Contact: zhao yun E-mail:zhaolee007@163.com

PDF

1237

被引次数

34

从水杨腈出发, 经醚化、两次成环、氯化制得4-氯-苯并[4,5]呋喃[3,2-d]嘧啶(); 与5-取代-2-巯基-1,3,4噻二唑反应, 合成了7个新的含噻二唑的苯并[4,5]呋喃[3,2-d]嘧啶衍生物. 其结构经H NMR, C NMR, IR和MS表征, 培养并测定化合物的晶体结构. 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, 其中化合物在10 μmol•L浓度下对PC3的抑制率为89.2%.

关键词: 水杨腈, 合成, 晶体结构, 抗癌活性

4-Chlorobenzo[4,5]furo[3,2-d]pyrimidine () was prepared from 2-hydroxybenzonitrile by etheration, cyclization and chlorization. Seven new compounds were synthesized by the reaction of with (5-substituted-2-thiol)-1,3,4-thiadiazole. Their structures were characterized by H NMR, C NMR, IR and MS techniques. Compound was investigated with X-ray crystallography. Preliminary bioassay indicates that some compounds possess antitumor activity to PC3 cells in vitro by MTT method. The antiproliferation activity of compound to PC3 cells at the concentration of 10 μmol•L was 89.2%.

Key words: 2-hydroxybenzonitrile, synthesis, crystal structure, antitumor activity