Ebrahim Saeedian Moghadam, Abdullah Mohammed Al-Sadi, Mahdis Sadeghi Moghadam, Bahareh Bayati, Meysam Talebi, Massoud Amanlou, Mohsen Amini, Raid Abdel-Jalil
{"title":"苯并咪唑-丙烯腈杂化衍生物是一种有效的脲酶抑制剂,可能具有杀菌活性。","authors":"Ebrahim Saeedian Moghadam, Abdullah Mohammed Al-Sadi, Mahdis Sadeghi Moghadam, Bahareh Bayati, Meysam Talebi, Massoud Amanlou, Mohsen Amini, Raid Abdel-Jalil","doi":"10.1080/17568919.2024.2393570","DOIUrl":null,"url":null,"abstract":"<p><p><b>Aim:</b> A series of benzimidazole-acrylonitrile derivatives <b>TM1-TM53</b> were designed with urease inhibition approach.<b>Materials & methods:</b> <b>TM1-TM53</b> were synthesized and characterized (<sup>1</sup>H Nuclear Magnetic Resonance (NMR), <sup>13</sup>C NMR, Mass Spectroscopy (MS) and IR) and subjected to urease inhibition assay using commercial assay kit. A molecular docking study was also performed using Autodock tool software.<b>Results:</b> Except six compounds, target molecules exhibited a higher urease inhibition effect (IC<sub>50</sub>: 1.22-28.45 μM) than hydroxyurea (IC<sub>50</sub>: 100 μM). kinetic study on <b>TM11</b>, clarified its mode of action as a mixed inhibitor. A molecular docking study on <b>TM6</b>, <b>TM11</b> and <b>TM21</b>, was performed and the results showed the main residues inside the active site of the enzyme. All <b>TM1-TM53</b> were also studied <i>in silico</i> using molecular docking techniques to evaluate their potential to inhibit succinate dehydrogenase in comparison to fluxapyroxad as standard. Docking study revealed the high potential of <b>TM1-TM53</b> as a fungicides.<b>Conclusion:</b> Obtained results exhibited the high activity of benzimidazole-acrylonitrile derivatives as urease inhibitors and their possible potential as fungicide agents. So, it will be beneficial to do more bioactivity investigation on this family of compounds.</p>","PeriodicalId":12475,"journal":{"name":"Future medicinal chemistry","volume":" ","pages":"2151-2168"},"PeriodicalIF":3.2000,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11559371/pdf/","citationCount":"0","resultStr":"{\"title\":\"Benzimidazole-acrylonitrile hybrid derivatives act as potent urease inhibitors with possible fungicidal activity.\",\"authors\":\"Ebrahim Saeedian Moghadam, Abdullah Mohammed Al-Sadi, Mahdis Sadeghi Moghadam, Bahareh Bayati, Meysam Talebi, Massoud Amanlou, Mohsen Amini, Raid Abdel-Jalil\",\"doi\":\"10.1080/17568919.2024.2393570\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p><b>Aim:</b> A series of benzimidazole-acrylonitrile derivatives <b>TM1-TM53</b> were designed with urease inhibition approach.<b>Materials & methods:</b> <b>TM1-TM53</b> were synthesized and characterized (<sup>1</sup>H Nuclear Magnetic Resonance (NMR), <sup>13</sup>C NMR, Mass Spectroscopy (MS) and IR) and subjected to urease inhibition assay using commercial assay kit. A molecular docking study was also performed using Autodock tool software.<b>Results:</b> Except six compounds, target molecules exhibited a higher urease inhibition effect (IC<sub>50</sub>: 1.22-28.45 μM) than hydroxyurea (IC<sub>50</sub>: 100 μM). kinetic study on <b>TM11</b>, clarified its mode of action as a mixed inhibitor. A molecular docking study on <b>TM6</b>, <b>TM11</b> and <b>TM21</b>, was performed and the results showed the main residues inside the active site of the enzyme. All <b>TM1-TM53</b> were also studied <i>in silico</i> using molecular docking techniques to evaluate their potential to inhibit succinate dehydrogenase in comparison to fluxapyroxad as standard. Docking study revealed the high potential of <b>TM1-TM53</b> as a fungicides.<b>Conclusion:</b> Obtained results exhibited the high activity of benzimidazole-acrylonitrile derivatives as urease inhibitors and their possible potential as fungicide agents. So, it will be beneficial to do more bioactivity investigation on this family of compounds.</p>\",\"PeriodicalId\":12475,\"journal\":{\"name\":\"Future medicinal chemistry\",\"volume\":\" \",\"pages\":\"2151-2168\"},\"PeriodicalIF\":3.2000,\"publicationDate\":\"2024-01-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11559371/pdf/\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Future medicinal chemistry\",\"FirstCategoryId\":\"3\",\"ListUrlMain\":\"https://doi.org/10.1080/17568919.2024.2393570\",\"RegionNum\":4,\"RegionCategory\":\"医学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2024/9/19 0:00:00\",\"PubModel\":\"Epub\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, MEDICINAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Future medicinal chemistry","FirstCategoryId":"3","ListUrlMain":"https://doi.org/10.1080/17568919.2024.2393570","RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/9/19 0:00:00","PubModel":"Epub","JCR":"Q3","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}
Benzimidazole-acrylonitrile hybrid derivatives act as potent urease inhibitors with possible fungicidal activity.
Aim: A series of benzimidazole-acrylonitrile derivatives TM1-TM53 were designed with urease inhibition approach.Materials & methods:TM1-TM53 were synthesized and characterized (1H Nuclear Magnetic Resonance (NMR), 13C NMR, Mass Spectroscopy (MS) and IR) and subjected to urease inhibition assay using commercial assay kit. A molecular docking study was also performed using Autodock tool software.Results: Except six compounds, target molecules exhibited a higher urease inhibition effect (IC50: 1.22-28.45 μM) than hydroxyurea (IC50: 100 μM). kinetic study on TM11, clarified its mode of action as a mixed inhibitor. A molecular docking study on TM6, TM11 and TM21, was performed and the results showed the main residues inside the active site of the enzyme. All TM1-TM53 were also studied in silico using molecular docking techniques to evaluate their potential to inhibit succinate dehydrogenase in comparison to fluxapyroxad as standard. Docking study revealed the high potential of TM1-TM53 as a fungicides.Conclusion: Obtained results exhibited the high activity of benzimidazole-acrylonitrile derivatives as urease inhibitors and their possible potential as fungicide agents. So, it will be beneficial to do more bioactivity investigation on this family of compounds.
期刊介绍:
Future Medicinal Chemistry offers a forum for the rapid publication of original research and critical reviews of the latest milestones in the field. Strong emphasis is placed on ensuring that the journal stimulates awareness of issues that are anticipated to play an increasingly central role in influencing the future direction of pharmaceutical chemistry. Where relevant, contributions are also actively encouraged on areas as diverse as biotechnology, enzymology, green chemistry, genomics, immunology, materials science, neglected diseases and orphan drugs, pharmacogenomics, proteomics and toxicology.