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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

 

E-mail: chshcao@jsnu.edu.cn

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.

DOI: 10.1007/s11696-019-00798-7

 

Chemical Papers 73 (10) 2477–2484 (2019)

Tuesday, October 15, 2019

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