In the present work, we reported the synthesis of Schiff bases from 4-phenoxy-5-sulfamoylbenzoic acid motif. The reaction was carried out by substitution of different aldehyde and ketones at sulfamoyl group of sulfamoylbenzoic acid. The generated substituted products (4a–4i) possessed potent structure activity relationship and exhibited drug like properties. The structures of synthesized compounds were characterized on the basis of FT-IR, 1H NMR, 13C NMR and mass spectroscopic data. The effects of synthesized products were investigated on urease enzyme through anti-urease enzyme inhibition assay (Weather burn method). These compounds were further evaluated for antibacterial potential. The Rationale behind the assessment of antibacterial activity was to investigate the synthesized compound's dual mode action against urease and virulent bacterial strains in order to develop a lead candidate for the treatment of GIT diseases such as gastric and peptic ulcers, as well as hepatic encephalopathy. The synthesized derivatives have outstanding anti-urease and antibacterial action, as is evident from in vitro and in silico studies. As a result, these compounds (3-(butylamino)-4-phenoxy-5-sulfamoylbenzoic acid; 4a-4i) might be explored further as a potential lead for the development of potent inhibitors in the future.
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Cover Image
The opportunistic bacterium Pseudomonas aeruginosa secretes the quorum-sensing molecule C12 to co-ordinate gene expression profiles favourable for infection. However, the influence of C12 on host cell physiology at concentrations observed in patients infected with P. aeruginosa is largely unknown. Our findings demonstrate that different concentrations of C12 impact distinct aspects of host airway epithelial cell physiology through PON2 activity in mitochondria. The cover image shows representative confocal images showing TMRE fluorescence in WT and PON-KO TECs after 25-min treatment with vehicle control (DMSO) or the indicated concentration of C12. Scale bar = 25 μm. For more information see the article by Whitt and colleagues (pp. 2013–2034) in this issue. The image is courtesy of Chi Li.
Synthesis, biochemical characterization and in silico investigation of 3-(butylamino)-4-phenoxy-5-sulfamoylbenzoic acid derivatives: dual action mode inhibitors of urease and virulent bacterial stains
Sajid Irshad, Saeed Ahmad, Shafi Ullah Khan, Mohsin Abbas Khan, Syeda Abida Ejaz, Huma Rao, Umair Khurshid, Aftab Ahmed, Nadeem Shahzad, Hamad M. Al-kahtani, Affan Waheed, Tanveer A. Wani, Abdullahi Tunde Aborode; Synthesis, biochemical characterization and in silico investigation of 3-(butylamino)-4-phenoxy-5-sulfamoylbenzoic acid derivatives: dual action mode inhibitors of urease and virulent bacterial stains. Biochem J 14 October 2022; 479 (19): 2035–2048. doi: https://doi.org/10.1042/BCJ20220395
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