ISSN print edition: 0366-6352
ISSN electronic edition: 1336-9075
Registr. No.: MK SR 9/7
Synthesis and antibacterial activity of fluorinated carbazoles
Sheng-liang Zhou, Hui-ling Tang, Miao Yao, Shi-nian Cao, Li-yuan Zhuang, Chang-sheng Cao, and Yan-hui Shi
Jiangsu Normal University, Xuzhou, People’s Republic of China
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: Fluorinated carbazole ; Antibacterial activity ; NDM-1 ; Structure–activity relationship
Full paper is available at www.springerlink.com.
Chemical Papers 73 (10) 2477–2484 (2019)