Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (1): 270-276.DOI: 10.6023/cjoc201808043 Previous Articles     Next Articles

Special Issue: 庆祝陈庆云院士九十华诞 元素有机化学合辑2018-2019

Notes

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

崔丽媛a, 陈煌冠a, 马静怡a, 韩建伟a,b, 王利民a   

  1. a 华东理工大学化学与分子工程学院 上海 200237;
    b 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
  • 收稿日期:2018-08-31 修回日期:2018-11-20 出版日期:2019-01-25 发布日期:2018-12-17
  • 通讯作者: 韩建伟, 王利民 E-mail:jianweihan@ecust.edu.cn;wanglimin@ecust.edu.cn
  • 基金资助:

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

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

Cui Liyuana, Chen Huangguana, Ma Jingyia, Han Jianweia,b, Wang Limina   

  1. a School of Chemistry & Molecular Engineering, East China University of Science and Technology, Shanghai 200237;
    b Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
  • Received:2018-08-31 Revised:2018-11-20 Online:2019-01-25 Published:2018-12-17
  • Contact: 10.6023/cjoc201808043 E-mail:jianweihan@ecust.edu.cn;wanglimin@ecust.edu.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21472213, 21772039), the National Key Research and Development Program (No. 2016YFA0200302), and by the Croucher Foundation (Hong Kong) in the Form of CAS-Croucher Foundation Joint Laboratory Grant.

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.

Key words: diaryliodonium salts, anti-bacterial, Kathon, fluorine, trifluoromethanesulfonate