邻三氟甲磺酸酯基取代二芳基碘盐的合成及其抑菌活性研究  

Synthesis of Vicinal Trifluoromethanesulfonate Substituted Diaryliodonium Salts and Their Anti-bacterial Properties

作　　者：崔丽媛 陈煌冠 马静怡 韩建伟 王利民[1] Cui Liyuan;Chen Huangguan;Ma Jingyi;Han Jianwei;Wang Limin(School of Chemistry & Molecular Engineering, East China University of Science and Technology, Shanghai 200237;Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032)

机构地区：[1]华东理工大学化学与分子工程学院,上海200237 [2]中国科学院上海有机化学研究所沪港化学合成联合实验室,上海200032

出　　处：《有机化学》2019年第1期270-276,共7页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(Nos.21472213,21772039);国家重点研发计划(No.2016YFA0200302);香港裘搓基金会资助项目~~

摘　　要：二芳基碘盐具有潜在的生物活性.合成了13种邻位三氟甲磺酸酯基取代的线性二芳基碘盐,利用核磁共振谱和质谱表征了它们的结构.通过微量肉汤稀释法测试该系列化合物的最低抑菌浓度(MIC),结果表明含氟基团取代的二芳基碘盐对于大肠杆菌(E.coli)、金黄色葡萄球菌(S.aureus)和枯草芽孢杆菌(B.subtilis)具有良好的抑菌性.其中,化合物(3-氟苯基)(2-(((三氟甲基)磺酰基)氧基)苯基)三氟甲磺酸碘盐(1)对大肠杆菌、金黄色葡萄球菌和枯草芽孢杆菌的MIC值分别为16,4,4μg·mL^-1,明显低于市售抗菌剂卡松(异噻唑啉酮).此外,扫描电子显微镜(SEM)结果显示,该二芳基碘盐能够明显诱导细菌死亡;细胞试验结果显示在体外条件下,化合物1与市售卡松对Hela细胞的生长影响相当,是一种低毒性的抗菌剂.Diaryliodonium salts with fluorines have potential bioactivity. Vicinal trifluoromethanesulfonate substituted diaryliodonium salts were synthesized for the purpose of studying their anti-bacterial properties aganist Escherichia coli (E. coli), Staphylococcus aureus (S. aureus) and Bacillus subtilis (B. subtilis). Firstly, their chemical structures were characterized by 1H NMR, 13C NMR, 19F NMR and mass spectra. The minimum inhibitory concentration (MIC) of these compounds was tested by the micro-broth dilution method. The most active 2-((3-fluorophenyl)(((trifluoromethyl)sulfonyl)oxy)-l3-iodanyl)- phenyl trifluoromethanesulfonate (1) containing fluorine group gave the promising results for Escherichia coli (E. coli), Staphylococcus aureus (S. aureus) and Bacillus subtilis (B. subtilis) (MIC values of 16, 4 and 4 μg·mL-1), which is significantly lower than the commercial antibacterial agent of isothiazolinones. Scanning electron microscope (SEM) analysis sugggested that the compound led to the death of bacteria. Cytotoxicity tests showed that the compound 1 as well as isothiazolinones had a slight effect on the growth of Hela cells in vitro conditions.

关 键 词：二芳基碘盐 抗菌剂 卡松 含氟化合物 三氟甲磺酸酯 

分 类 号：O621.25[理学—有机化学] TQ465[理学—化学]