Abstract
In our previous studies, fluorine-substituted carbazoles were synthesized, and these compounds showed promising potential against Gram-positive bacterial stains, including Methicillin-resistant Staphylococcus aureus. However, only three compounds with two F substituents on the 2,4-positions of carbazole showed antibacterial potency against both Gram-positive and Gram-negative bacterial strains. A series of new compounds with two F substituents on the 2,4-positions of carbazole, besides three known ones, were synthesized. The structures were confirmed by infrared spectroscopy, 1H & 13C nuclear magnetic resonance spectroscopy, and high-resolution mass spectrometry. Eight compounds showed antibacterial activity. 2,4,6-Trifluoro-9H-carbazole (2), with simple structure, showed potential antibacterial activity against the multidrug resistant NDM-1-producing strains which are not inhibited by commonly used antibiotics. Its water-soluble salt was synthesized but showed less activity.
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Acknowledgements
This study was supported by the fund of National Nature Science Foundation of China (Project number 21571087 and 31300067), the Major Projects of Natural Science Foundation of the Jiangsu Higher Education Institutions of China (Grant numbers 15KJA180002 and 15KJA150004), and the Open-end Funds of Jiangsu Key Laboratory of Marine Biotechnology, Huaihai Institute of Technology (Grant number 2015HS003).
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Zhou, Sl., Tang, Hl., Yao, M. et al. Synthesis and antibacterial activity of fluorinated carbazoles. Chem. Pap. 73, 2477–2484 (2019). https://doi.org/10.1007/s11696-019-00798-7
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DOI: https://doi.org/10.1007/s11696-019-00798-7