Academic Journal
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.
| Τίτλος: | 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. |
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| Συγγραφείς: | Irshad S; Department of Pharmaceutical Chemistry, Faculty of Pharmacy, The Islamia University of Bahawalpur, Bahawalpur, Pakistan., Ahmad S; Department of Pharmaceutical Chemistry, Faculty of Pharmacy, The Islamia University of Bahawalpur, Bahawalpur, Pakistan., Khan SU; Product and Process Innovation Department, Qarshi Brands Pvt. Ltd., Hattar Industrial Estate-22610, Haripur, KPK Pakistan., Khan MA; Department of Pharmaceutical Chemistry, Faculty of Pharmacy, The Islamia University of Bahawalpur, Bahawalpur, Pakistan., Ejaz SA; Department of Pharmaceutical Chemistry, Faculty of Pharmacy, The Islamia University of Bahawalpur, Bahawalpur, Pakistan., Rao H; Department of Pharmaceutical Chemistry, Faculty of Pharmacy, The Islamia University of Bahawalpur, Bahawalpur, Pakistan., Khurshid U; Department of Pharmaceutical Chemistry, Faculty of Pharmacy, The Islamia University of Bahawalpur, Bahawalpur, Pakistan., Ahmed A; Department of Pharmaceutical Chemistry, Faculty of Pharmacy, The Islamia University of Bahawalpur, Bahawalpur, Pakistan., Shahzad N; Department of Pharmaceutical Chemistry, Faculty of Pharmacy, The Islamia University of Bahawalpur, Bahawalpur, Pakistan., Al-Kahtani HM; Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia., Waheed A; Department of Pharmaceutical Chemistry, Faculty of Pharmacy, The Islamia University of Bahawalpur, Bahawalpur, Pakistan., Wani TA; Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia., Aborode AT; Department of Chemistry, Mississippi State University, Starkville, U.S.A. |
| Πηγή: | The Biochemical journal [Biochem J] 2022 Oct 14; Vol. 479 (19), pp. 2035-2048. |
| Τύπος έκδοσης: | Journal Article; Research Support, Non-U.S. Gov't |
| Γλώσσα: | English |
| Στοιχεία περιοδικού: | Publisher: Published by Portland Press on behalf of the Biochemical Society Country of Publication: England NLM ID: 2984726R Publication Model: Print Cited Medium: Internet ISSN: 1470-8728 (Electronic) Linking ISSN: 02646021 NLM ISO Abbreviation: Biochem J Subsets: MEDLINE |
| Imprint Name(s): | Original Publication: London, UK : Published by Portland Press on behalf of the Biochemical Society |
| Ιατρικοί όροι (MeSH): | Schiff Bases*/chemistry , Urease*/chemistry , Urease*/metabolism, Anti-Bacterial Agents/pharmacology ; Bacteria/metabolism ; Coloring Agents/pharmacology ; Enzyme Inhibitors/chemistry ; Enzyme Inhibitors/pharmacology ; Ketones/pharmacology ; Aldehydes ; Benzoates ; Molecular Docking Simulation ; Molecular Structure ; Spectroscopy, Fourier Transform Infrared ; Structure-Activity Relationship |
| Περίληψη: | 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. (© 2022 The Author(s). Published by Portland Press Limited on behalf of the Biochemical Society.) |
| Contributed Indexing: | Keywords: Schiff base; bacterial activity; docking; urease |
| Substance Nomenclature: | 0 (Aldehydes) 0 (Anti-Bacterial Agents) 0 (Benzoates) 0 (Coloring Agents) 0 (Enzyme Inhibitors) 0 (Ketones) 0 (Schiff Bases) 30Z5HQB5A4 (carzenide) EC 3.5.1.5 (Urease) |
| Entry Date(s): | Date Created: 20220916 Date Completed: 20221010 Latest Revision: 20221130 |
| Update Code: | 20260130 |
| DOI: | 10.1042/BCJ20220395 |
| PMID: | 36111588 |
| Βάση Δεδομένων: | MEDLINE |
| ISSN: | 1470-8728 |
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| DOI: | 10.1042/BCJ20220395 |