Citation: Cui Liyuan, Chen Huangguan, Ma Jingyi, Han Jianwei, Wang Limin. Synthesis of Vicinal Trifluoromethanesulfonate Substituted Diaryliodonium Salts and Their Anti-bacterial Properties[J]. Chinese Journal of Organic Chemistry, ;2019, 39(1): 270-276. doi: 10.6023/cjoc201808043 shu

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

Cui Liyuan ^a ,
Chen Huangguan ^a ,
Ma Jingyi ^a ,
Han Jianwei ^a,b,, ,
Wang Limin ^a,,

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

Corresponding author: Han Jianwei, jianweihan@ecust.edu.cn Wang Limin, wanglimin@ecust.edu.cn
Received Date: 31 August 2018
Revised Date: 20 November 2018
Available Online: 17 January 2018
Fund Project: the National Natural Science Foundation of China 21772039the National Key Research and Development Program 2016YFA0200302Project 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 Grantthe National Natural Science Foundation of China 21472213

Figures(6)

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.
- diaryliodonium salts,
- anti-bacterial,
- Kathon,
- fluorine,
- trifluoromethanesulfonate
1. [1]
  Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2008, 108, 5299. doi: 10.1021/cr800332c
2. [2]
  Chen, H.; Han, J.; Wang L. Angew. Chem., Int. Ed. 2018, 57, 12313. doi: 10.1002/anie.201806405
3. [3]
  Zhang, Y.; Han, J.; Liu, Z.-J. RSC Adv. 2015, 5, 25485. doi: 10.1039/C5RA00209E
4. [4]
  Kuik, W.-J.; Kema, I. P.; Brouwers, A. H.; Zijlma, R.; Neumann, K. D.; Dierckx, R. A. J. O.; DiMagno, S. G.; Elsinga, P. H. J. Nucl. Med. 2015, 56, 106. doi: 10.2967/jnumed.114.145730
5. [5]
  DeSolms, S. J.; Woltersdorf, O. W., Jr.; Cragoe, E. J., Jr.; Watson, L. S.; Fanelli, G. M., Jr. J. Med. Chem. 1978, 215, 437.
6. [6]
  Das, P.; Etsuko T.; Tokunaga, H.; Akiyama, H.; Doi, H.; Saito, N.; Shibata, N. Beilstein J. Org. Chem. 2018, 14, 364. doi: 10.3762/bjoc.14.24
7. [7]
  Goldstein, E. J. C.; Citron, D. M.; Warren, Y.; Merriam, C. V.; Tyrrell, K.; Fernandez, H.; Radhakrishnan, U.; Stang, P. J.; Conrads, G. Antimicrob. Agents Chemother. 2004, 48, 2766. doi: 10.1128/AAC.48.7.2766-2770.2004
8. [8]
  Lu, J.; Risbood, P.; Kane, C. T., Jr.; Hossain, M. T.; Anderson, L.; Hill, K.; Monks, A.; Wu, Y.; Antony, S.; Juhasz, A.; Liu, H.; Jiang, G.; Harris, E.; Roy, K.; Meitzler, J. L.; Konaté, M.; Doroshow, J. H. Biochem. Pharmacol. 2017, 143, 25.
9. [9]
  Hui, F.; Debiemme-Chouvy, C. Biomacromolecules 2013, 14, 585. doi: 10.1021/bm301980q
10. [10]
  Dong, A.; Wang, Y.-J.; Gao, Y.; Gao, T.; Gao G. Chem. Rev. 2017, 117, 4806. doi: 10.1021/acs.chemrev.6b00687
11. [11]
  Gottardi, W.; Debabov, D.; Nagl, M. Antimicrob. Agents Chemother. 2013, 57, 1107. doi: 10.1128/AAC.02132-12
12. [12]
  Fang, G.; Li, W.; Shen, X.; Perez-Aguilar, J. M.; Chong, Y.; Gao, X..; Chai, Z.; Chen, C.; Ge, C.; Zhou, R. Nat. Commun. 2018, 9, 129. doi: 10.1038/s41467-017-02502-3
13. [13]
  Hoque, J.; Akkapeddi, P.; Yarlagadda, V.; Uppu. D. S. S. M.; Kumar, P.; Haldar, J. Langmuir 2012, 28, 12225. doi: 10.1021/la302303d
14. [14]
  Li, Y.-K.; Liu, B.; Zhang, L.-J.; Zhu, J.-H.; Wan, C.-P.; Mao, Z.-W. Chin. J. Org. Chem. 2018, 38, 949(in Chinese).
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