J. Gogoi, B. Chetia, J. G. Handique, S. Saikia, P. Chetia
{"title":"Design, Synthesis, and Antibacterial Evaluation of Novel Coumarin Based 1,2,3-Triazole Derivatives","authors":"J. Gogoi, B. Chetia, J. G. Handique, S. Saikia, P. Chetia","doi":"10.1134/s1068162024040198","DOIUrl":null,"url":null,"abstract":"<h3 data-test=\"abstract-sub-heading\">Abstract</h3><p><b>Objective:</b> Coumarin and triazole moiety itself is well known to have wide range of biological properties including antibacterial activities. In this work, we have designed and synthesized a series of novel coumarin based 1,2,3-triazole derivatives (<b>VIa–VIi</b>) and reported them as potent antibacterial agent. <b>Methods:</b> All the synthesized compounds were characterized using different spectroscopic methods. The antibacterial properties of our designed compounds were evaluated by calculating the minimum inhibitory concentration (MIC) against the bacterial panel <i>Escherichia coli</i> (<i>E. coli</i>), <i>Pseudomonas aeruginosa</i> (<i>P. aeruginosa</i>), <i>Staphylococcus aureus</i> (<i>S. aureus</i>), and <i>Bacillus subtilis</i> (<i>B. subtilis</i>). Further, molecular docking analysis were also performed in order to determine the binding modes and binding energies of the potent hybrids. The <i>in silico</i> method has been used for determining the absorption, distribution, metabolism, excretion, and toxicity (ADMET) properties of (<b>VIc</b>), (<b>VId</b>), (<b>VIg</b>), and (<b>VIh</b>). <b>Results and Discussion:</b> Here, we have successfully synthesized nine novel coumarin based 1,2,3-triazole conjugates using cycloaddition reaction. All the compounds were found to be active against the tested bacterial panel with MIC values ranging from 12.5 to 200 µg/mL. Among them four compounds (<b>VIc</b>), (<b>VId</b>), (<b>VIg</b>), and (<b>VIh</b>) showed broad spectrum of antibacterial activities. Out of these four, the compound (<b>VIh</b>) showed excellent inhibitory action against <i>B. subtilis</i> and compounds (<b>VIg</b>), (<b>VIh</b>) showed great inhibition activity against <i>S. aureus</i> in comparison to the standard drug streptomycin. The molecular docking study also revealed the binding capabilities of our designed compounds with the different active site of the protein (PDB ID: 4OZ5) extracted from <i>B. subtilis</i> with great affinity. <b>Conclusions:</b> From the calculated MIC values, we can conclude that our compounds can act as a potent antibacterial agent against the tested bacteria panel. The <i>in silico</i> results also help to understand the mode of inhibitory action and justify the potential of the synthesized compounds as excellent antibacterial agent.</p>","PeriodicalId":758,"journal":{"name":"Russian Journal of Bioorganic Chemistry","volume":null,"pages":null},"PeriodicalIF":1.1000,"publicationDate":"2024-08-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Russian Journal of Bioorganic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1134/s1068162024040198","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
引用次数: 0
Abstract
Objective: Coumarin and triazole moiety itself is well known to have wide range of biological properties including antibacterial activities. In this work, we have designed and synthesized a series of novel coumarin based 1,2,3-triazole derivatives (VIa–VIi) and reported them as potent antibacterial agent. Methods: All the synthesized compounds were characterized using different spectroscopic methods. The antibacterial properties of our designed compounds were evaluated by calculating the minimum inhibitory concentration (MIC) against the bacterial panel Escherichia coli (E. coli), Pseudomonas aeruginosa (P. aeruginosa), Staphylococcus aureus (S. aureus), and Bacillus subtilis (B. subtilis). Further, molecular docking analysis were also performed in order to determine the binding modes and binding energies of the potent hybrids. The in silico method has been used for determining the absorption, distribution, metabolism, excretion, and toxicity (ADMET) properties of (VIc), (VId), (VIg), and (VIh). Results and Discussion: Here, we have successfully synthesized nine novel coumarin based 1,2,3-triazole conjugates using cycloaddition reaction. All the compounds were found to be active against the tested bacterial panel with MIC values ranging from 12.5 to 200 µg/mL. Among them four compounds (VIc), (VId), (VIg), and (VIh) showed broad spectrum of antibacterial activities. Out of these four, the compound (VIh) showed excellent inhibitory action against B. subtilis and compounds (VIg), (VIh) showed great inhibition activity against S. aureus in comparison to the standard drug streptomycin. The molecular docking study also revealed the binding capabilities of our designed compounds with the different active site of the protein (PDB ID: 4OZ5) extracted from B. subtilis with great affinity. Conclusions: From the calculated MIC values, we can conclude that our compounds can act as a potent antibacterial agent against the tested bacteria panel. The in silico results also help to understand the mode of inhibitory action and justify the potential of the synthesized compounds as excellent antibacterial agent.
期刊介绍:
Russian Journal of Bioorganic Chemistry publishes reviews and original experimental and theoretical studies on the structure, function, structure–activity relationships, and synthesis of biopolymers, such as proteins, nucleic acids, polysaccharides, mixed biopolymers, and their complexes, and low-molecular-weight biologically active compounds (peptides, sugars, lipids, antibiotics, etc.). The journal also covers selected aspects of neuro- and immunochemistry, biotechnology, and ecology.