5-(4-fluoro-2-nitrophenyl)-3-phenyl-1,2,4-oxadiazole | 1609643-63-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-fluoro-2-nitrophenyl)-3-phenyl-1,2,4-oxadiazole
• 英文别名: 5-(4-Fluoro-2-nitrophenyl)-3-phenyl-1,2,4-oxadiazole
• CAS: 1609643-63-1
• 化学式: C₁₄H₈FN₃O₃
• 分子量: 285.234
• InChiKey: XNRDYHRFVYFIHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  苯甲酰胺肟 、 4-氟-2-硝基苯甲酰氯 在 三氟化硼乙醚 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.5h， 生成 5-(4-fluoro-2-nitrophenyl)-3-phenyl-1,2,4-oxadiazole
  参考文献：
  名称：

  Bis-aryloxadiazoles as effective activators of the aryl hydrocarbon receptor

  摘要：

  Bis-aryloxadiazoles are common scaffolds in medicinal chemistry due to their wide range of biological activities. Previously, we identified a 1,2,4-bis-aryloxadiazole that blocks mammary branching morphogenesis through activation of the aryl hydrocarbon receptor (AHR). In addition to defects in mammary differentiation, AHR stimulation induces toxicity in many other tissues. We performed a structure activity relationship (SAR) study of 1,2,4-bis-aryloxadiazole to determine which moieties of the molecule are critical for AHR activation. We validated our results with a functional biological assay, using desmosome formation during mammary morphogenesis to indicate AHR activity. These findings will aid the design of oxadiazole derivative therapeutics with reduced off-target toxicity profiles. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.013