2-(benzoimidazol-5-yl)-5-(4-fluorophenyl)-1,3,4-oxadiazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-(benzoimidazol-5-yl)-5-(4-fluorophenyl)-1,3,4-oxadiazole
• 英文别名: 2-(3H-benzimidazol-5-yl)-5-(4-fluorophenyl)-1,3,4-oxadiazole
• 化学式: C₁₅H₉FN₄O
• 分子量: 280.261
• InChiKey: HYZPDSLXWFUBSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.42
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.6
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  1H-苯并咪唑-6-羧酸乙酯 在 一水合肼 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 48.5h， 生成 2-(benzoimidazol-5-yl)-5-(4-fluorophenyl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Design and evaluation of Nrf2 activators with 1,3,4-oxa/thiadiazole core as neuro-protective agents against oxidative stress in PC-12 cells

  摘要：

  Oxidative stress plays vital roles in virous neurodegenerative diseases including Alzheimer's disease. Activation of the transcription factor Nrf2 (nuclear factor erythroid 2-related factor 2), the key regulator of oxidative stress, may provide a new therapeutic strategy for these diseases. Herein we synthesized and evaluated a series of 1,3,4-oxa/thiadiazole core Nrf2 activators as neuroprotective agents. The representative compound 8 exhibited cytoprotective and Nrf2 activation effects in a neuron-like PC-12 cells. Additionally, compound 8 showed good membrane permeability, indicating this compound could penetrate blood-brain barrier (BBB) to reach central nervous system (CNS) as a neuro-protective agent. These results indicated that these Nrf2 activators with 1,3,4-oxa/thiadiazole core could serve as a new chemotype against oxidative stress in neurodegenerative diseases.

  DOI：

  10.1016/j.bmcl.2019.126853