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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
Biochemical Journal ( IF 4.1 ) Pub Date : 2022-10-14 , DOI: 10.1042/bcj20220395
Sajid Irshad 1 , Saeed Ahmad 1 , Shafi Ullah Khan 2 , Mohsin Abbas Khan 1 , Syeda Abida Ejaz 1 , Huma Rao 1 , Umair Khurshid 1 , Aftab Ahmed 1 , Nadeem Shahzad 1 , Hamad M Al-Kahtani 3 , Affan Waheed 1 , Tanveer A Wani 3 , Abdullahi Tunde Aborode 4
Affiliation  

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.

中文翻译:

3-(丁氨基)-4-苯氧基-5-氨磺酰基苯甲酸衍生物的合成、生化表征和计算机研究:脲酶和剧毒细菌污渍的双重作用模式抑制剂

在目前的工作中,我们报道了从 4-苯氧基-5-氨磺酰基苯甲酸基序合成席夫碱。该反应是通过不同的醛和酮在氨磺酰苯甲酸的氨磺酰基上的取代而进行的。生成的取代产物 (4a–4i) 具有有效的结构活性关系并表现出药物样特性。基于 FT-IR、1H NMR、13C NMR 和质谱数据对合成化合物的结构进行了表征。通过抗脲酶抑制试验(Weather burn法)研究合成产物对脲酶的影响。进一步评估了这些化合物的抗菌潜力。抗菌活性评估背后的基本原理是研究合成的化合物' s 对脲酶和毒性细菌菌株的双重模式作用,以开发用于治疗 GIT 疾病(如胃和消化性溃疡以及肝性脑病)的主要候选药物。合成的衍生物具有出色的抗尿素酶和抗菌作用,体外和计算机研究证明了这一点。因此,这些化合物(3-(丁氨基)-4-苯氧基-5-氨磺酰基苯甲酸;4a-4i)可能会作为未来开发强效抑制剂的潜在线索而得到进一步探索。
更新日期:2022-10-07
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