苯并咪唑并[2,1-b]噻唑衍生物的合成  

Synthesis of Benzimidazolo[2,1-b]thiazole Derivatives

作　　者：叶姗姗 李婷婷[1] 王晨 赵子任 张变香[1] YE Shan-shan;LI Ting-ting;WANG Chen;ZHAO Zi-ren;ZHANG Bian-xiang(School of Chemistry and Chemical Engineering,Shanxi University,Taiyuan 030006,China)

机构地区：[1]山西大学化学化工学院,山西太原030006

出　　处：《合成化学》2020年第3期215-221,共7页Chinese Journal of Synthetic Chemistry

基　　金：国家自然科学基金资助项目(21971154);山西省科技厅人才专项(2018043)。

摘　　要：以2-巯基咪唑类化合物为原料,室温下与含有端基炔的二芳基高碘盐反应,一步合成苯并咪唑并[2,1-b]噻唑衍生物,其结构经1H NMR、13C NMR、单晶X-衍射和HR-MS表征。在最佳反应条件[n(2-巯基苯并咪唑)/n(二芳基高碘盐)=1/1,二氯甲烷为溶剂,反应12 h]下,目标化合物的产率最高为84%。同时对该反应的机理进行了详细探讨,并采用MTT法研究了目标化合物对人肝癌细胞(HepG2)生长情况的影响。结果表明:当浓度为4μg/mL时,化合物3b具有较强的抑制HepG2细胞增殖的活性,抑制率为52%。Three benzimidazole[2,1-b]thiazole derivatives were synthesized by the reaction of 2-mercaptoimidazole derivatives with diaryliodonium salt containing terminal alkynes at room temperature without the existence of metal catalysts, ligands and alkalis. The target compounds were characterized by 1H NMR, 13C NMR, single crystal X-ray and HR-MS, and the optimum reaction conditions were determined. It showed that the yield of target product was up to 84% when the molar ratio of benzo-2-mercaptobenzimidazole to diaryliodonium salt was 1/1, dichloromethane as solvent, and the reaction time was 12 h at room temperature. At the same time, the mechanism of the reaction was discussed, and the effects of different concentrations of these compounds on the growth of human hepatoma cells(HepG2) were studied by MTT method. The results showed that compound 3 b had a strong inhibitory activity against HepG2 cell proliferation at a concentration of 4 μg/mL, and the inhibition rate was 52%.

关 键 词：苯并咪唑并[2 1-b]噻唑 2-巯基苯并咪唑 二芳基高碘盐 端基炔 合成 

分 类 号：O623.626[理学—有机化学] O621.3[理学—化学]