Scholarlink

<p>We have developed a simple and environmentally benign multi step method for synthesising 3,5-disubstituted-1,2,4-oxadiazoles under basic conditions via the cyclodehydration of amidoxime with carbonyldiimidazole. This approach offers several advantages, including good yields, a straightforward procedure, low cost, short reaction times, and utility for library synthesis in industrial applications. All synthesised compounds in this new series of 1,2,4-oxadiazoles were characterized using instrumental techniques such as <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy and mass spectrometry (LCMS). A series of novel 1,2,4-oxadiazole derivatives were synthesized and evaluated for their in vitro antibacterial and antioxidant activities. The antibacterial screening revealed that all tested compounds exhibited potent activity, comparable to the reference drug, with variations in efficacy depending on specific structural modifications. Among them, compound 10g demonstrated the highest antibacterial activity, with a minimum inhibitory concentration (MIC) of 5&#xa0;μg/mL against <i>Escherichia coli</i> and <i>Bacillus subtilis</i>, while compound 10h exhibited an MIC of 10&#xa0;μg/mL. Antioxidant assessments identified compound 10f, which features a 2-hydroxy-6-methylpyridine linker, as the most promising antioxidant, with IC50 values of 22 ± 2.8&#xa0;μg/mL for DPPH radical scavenging and 25 ± 4.4&#xa0;μg/mL for hydroxyl radical scavenging. Density functional theory (DFT) calculations using implicit solvation models revealed energy gaps of 4.3223&#xa0;eV for 10f and 4.3378&#xa0;eV for 10g, indicating favorable electronic properties. Molecular docking studies predicted that 10g interacts with <i>B. subtilis</i> TagU, while 10f exhibits strong binding affinity toward rhomboid protease and NAD(P)H oxidase, findings further corroborated by molecular dynamics simulations. These insights highlight the therapeutic potential of these oxadiazole derivatives for antibacterial and antioxidant applications.</p>

错误：搜索内容不能为空，请输入英文关键词
错误：关键词超出字数限制，请精简
高级检索

Development of novel 3, 5-substituted-1,2,4-oxadiazole derivatives: a multidimensional approach with in vitro antibacterial, antioxidant, DFT insights, and molecular dynamics simulations

  • 期刊论文

  • 出版模式：

    开放获取

  • 发表日期：

    2025年7月29日

查看全文
  • Nandeesh Kebbahalli Nagalingaiah,
  • Vivek Hamse Kameshwar,
  • Shwetha Hosahalli Nanjundappa,
  • Shivakumaraswamy Komalapura Ningegowda,
  • Mantelingu Kempegowda

摘要

We have developed a simple and environmentally benign multi step method for synthesising 3,5-disubstituted-1,2,4-oxadiazoles under basic conditions via the cyclodehydration of amidoxime with carbonyldiimidazole. This approach offers several advantages, including good yields, a straightforward procedure, low cost, short reaction times, and utility for library synthesis in industrial applications. All synthesised compounds in this new series of 1,2,4-oxadiazoles were characterized using instrumental techniques such as 1H and 13C NMR spectroscopy and mass spectrometry (LCMS). A series of novel 1,2,4-oxadiazole derivatives were synthesized and evaluated for their in vitro antibacterial and antioxidant activities. The antibacterial screening revealed that all tested compounds exhibited potent activity, comparable to the reference drug, with variations in efficacy depending on specific structural modifications. Among them, compound 10g demonstrated the highest antibacterial activity, with a minimum inhibitory concentration (MIC) of 5 μg/mL against Escherichia coli and Bacillus subtilis, while compound 10h exhibited an MIC of 10 μg/mL. Antioxidant assessments identified compound 10f, which features a 2-hydroxy-6-methylpyridine linker, as the most promising antioxidant, with IC50 values of 22 ± 2.8 μg/mL for DPPH radical scavenging and 25 ± 4.4 μg/mL for hydroxyl radical scavenging. Density functional theory (DFT) calculations using implicit solvation models revealed energy gaps of 4.3223 eV for 10f and 4.3378 eV for 10g, indicating favorable electronic properties. Molecular docking studies predicted that 10g interacts with B. subtilis TagU, while 10f exhibits strong binding affinity toward rhomboid protease and NAD(P)H oxidase, findings further corroborated by molecular dynamics simulations. These insights highlight the therapeutic potential of these oxadiazole derivatives for antibacterial and antioxidant applications.