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有机化学.pdfVIP

2010 年第 30 卷 有 机 化 学 Vol. 30, 2010 第 7 期, 1093～1097 Chinese Journal of Organic Chemistry No. 7, 1093～1097 ·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 (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) 摘要 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(5); 5 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 1H NMR, 13C NMR, IR 和 MS 表征, 培养 并测定化合物 6a 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 6b 在 10 µmol•L－1 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 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, Guiping* Xu, Weiming Jin, Linhong Yuan, Kai (Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Research and Development Cen- ter of Fine Chemicals, Guizhou University, Guiyang 550025) Abstract 4-Chlorobenzo[4,5]furo[3,2-d]pyrimidine (5) was prepared from 2-hydroxybenzonitrile by ether- ation, cyclization and chlorization. Seven new compounds were synthesized by the reaction of 5 with 1 13 (5-substituted-2-thiol)-1,3,4-thiadiazole. Their structures were characterized by H NMR, C NMR, IR and MS techniques. Compound 6a was investigated with X-ray crystallography. Preliminary bioassay indicates that some compounds p