3-phenyl-4-prop-2-ynyl-4H-[1,2,4]oxadiazol-5-one | 14372-36-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-phenyl-4-prop-2-ynyl-4H-[1,2,4]oxadiazol-5-one
• CAS: 14372-36-2
• 化学式: C₁₁H₈N₂O₂
• 分子量: 200.197
• InChiKey: YHHFDXRETZWZMY-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  3-phenyl-4-prop-2-ynyl-4H-[1,2,4]oxadiazol-5-one 在 copper(l) iodide 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-(1H-indol-3-yl)-2-(4-{4-[(5-oxo-3-phenyl-1,-2,4-oxadiazol-4(5H)-yl)methyl]-1H-1,2,3-triazol-1-yl}benzamido)methyl propanoate
  参考文献：
  名称：

  New oxadiazol‐5‐ones derivatives and their performance as angiotensin‐converting enzyme (ACE) inhibitors

  摘要：

  Angiotensin‐converting enzyme inhibitors are widely used in treating arterial hypertension, acting on the renin‐angiotensin‐aldosterone system and controlling blood pressure. We present a novel, greener, and faster methodology to assess the 1,2,4‐oxadiazol‐5‐one ring and perform molecular modifications to obtain angiotensin‐converting enzyme (ACE) inhibitors using this heterocyclic core. Molecular docking simulations indicate that the tested compounds exhibited an affinity for the ACE binding site, with scores comparable to the commercial inhibitor lisinopril. However, in vitro assays revealed that the compounds were ineffective in inhibiting ACE activity. The lack of inhibition may be related to the compounds' more apolar nature. These results emphasize the importance of integrating computational and experimental approaches in developing new drugs, providing valuable insights for planning future studies to optimize the activity of synthesized compounds.

  DOI：

  10.1002/jhet.4835
• 作为产物：
  描述：

  O-(ethoxycarbonyl)benzohydroxamamide 在 水 、 potassium carbonate 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 3-phenyl-4-prop-2-ynyl-4H-[1,2,4]oxadiazol-5-one
  参考文献：
  名称：

  Discovery of novel heterocyclic derivatives containing oxadiazolone or pyrimidinone cores as DPP‐4 inhibitors

  摘要：

  Type 2 diabetes is a chronic disease characterized by insulin resistance and alterations in incretin secretion, such as the glucagon‐like peptide‐1 (GLP‐1) hormone. GLP‐1 plays a crucial role in signaling insulin production in the pancreas, with its activity regulated by the dipeptidyl peptidase 4 (DPP‐4) enzyme. DPP‐4 presents an intriguing strategy for controlling type 2 diabetes. This study focuses on synthesizing 22 novel oxadiazolone and pyrimidinone derivatives, in vitro DPP‐4 inhibition, and elucidating binding modes through molecular docking simulations. Nine compounds showed promising inhibitory activity, with IC50 values ranging from 0.3 to 1.86 mM. Molecular docking simulations revealed interactions between these compounds and critical residues in the enzyme's active site, such as Arg125, Glu206, Ser630, and His740. This investigation introduces a new class of DPP‐4 inhibitors, providing insights into the design of more potent molecules as potential candidates for combating type 2 diabetes. The findings contribute to developing innovative therapeutics for managing this prevalent metabolic disorder.

  DOI：

  10.1002/jhet.4811