Chinese Journal of Organic Chemistry >
Design, Synthesis and Antibacterial Activity of 1,3,4-Oxadiazole Sufones Containing Sulfonamide Structure
Received date: 2022-04-28
Revised date: 2022-07-19
Online published: 2022-08-18
Supported by
National Key Research and Development Program of China(2021YFD1400800); Natural Science Foundation of Guizhou Province(QKHJC-ZK[2022]039); Natural Science Foundation of Guizhou University((2021)01)
To discover new antibacterial agents, twenty-three 1,3,4-oxadiazolsulfone compounds containing a sulfonamide structure were designed and synthesized by active substructure splicing, and their antibacterial activities were tested. Most of the compounds exhibited excellent in vitro antibacterial activity against Xanthomonas oryzae pv. oryzicola (Xoc) and Xanthomonas oryzae pv. oryzae (Xoo) at a concentration of 100 µg/mL. Except for N-((5-(propylsulfonyl)-1,3,4-oxadiazo- 2-yl)methyl)-4-(trifluoromethyl)benzenesulfonamide (18), the median effective concentration (EC50) values of other compounds against Xoc were 1.3~22.5 µg/mL, and the EC50 of all compounds against Xoo were 1.1~32.7 µg/mL, which were better than the control agents bismerthiazol (84.1 and 71.4 µg/mL) and thiodiazole copper (122.1 and 84.0 µg/mL). In addition, 4-fluoro-N-((5-(methylsulfonyl)-1,3,4-oxadiazole-2-yl)methyl)benzenesulfonamide (4) can inhibit the growth of Xoc and Xoo by inhibiting the production of exopolysaccharide (EPS) and the formation of biofilm, changing the permeability of cell membrane and cell surface morphology.
Yifang Chen , Xin Luo , Yu Wang , Zhifu Xing , Ju Peng , Jixiang Chen . Design, Synthesis and Antibacterial Activity of 1,3,4-Oxadiazole Sufones Containing Sulfonamide Structure[J]. Chinese Journal of Organic Chemistry, 2023 , 43(1) : 274 -284 . DOI: 10.6023/cjoc202204068
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