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Synthesis and antibacterial activity of fluorinated carbazoles

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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… Click to show full 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.

Keywords: synthesis antibacterial; antibacterial activity; activity fluorinated; fluorinated carbazoles; spectroscopy; activity

Journal Title: Chemical Papers
Year Published: 2019

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