4-bromo-2-(4-fluorophenyl)benzoxazole | 1381869-39-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-bromo-2-(4-fluorophenyl)benzoxazole
• 英文别名: 4-bromo-2-(4-fluorophenyl)benzo[d]oxazole；4-Bromo-2-(4-fluorophenyl)-1,3-benzoxazole；4-bromo-2-(4-fluorophenyl)-1,3-benzoxazole
• CAS: 1381869-39-1
• 化学式: C₁₃H₇BrFNO
• 分子量: 292.107
• InChiKey: MBHDOZQODZREKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-甲氧基-4-(4-甲基-1H-咪唑-1-基)苯胺 、 4-bromo-2-(4-fluorophenyl)benzoxazole 在 tris-(dibenzylideneacetone)dipalladium(0) 、 caesium carbonate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 叔丁醇 为溶剂， 反应 20.0h， 以40%的产率得到[2-(4-fluorophenyl)benzoxazol-4-yl]-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]amine
  参考文献：
  名称：

  Design and Synthesis of a Novel Series of Bicyclic Heterocycles As Potent γ-Secretase Modulators

  摘要：

  The design and the synthesis of several chemical subclasses of imidazole containing gamma-secretase modulators (GSMs) is described. Conformational restriction of pyridone 4 into bicyclic pyridone isosteres has led to compounds with high in vitro and in vivo potency. This has resulted, in the identification of benzimidazole 44a as a GSM with low nanomolar potency in vitro. In mouse, rat, and dog, this compound displayed the typical gamma-secretase modulatory profile by lowering A beta 42 and A beta 40 levels combined with an especially pronounced increase in A beta 38 and A beta 37 levels while leaving the total levels of amyloid peptides unchanged.

  DOI：

  10.1021/jm201710f
• 作为产物：
  描述：

  2,6-二溴苯胺 在 copper(l) iodide 、 1,10-菲罗啉 、 caesium carbonate 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 生成 4-bromo-2-(4-fluorophenyl)benzoxazole
  参考文献：
  名称：

  Design and Synthesis of a Novel Series of Bicyclic Heterocycles As Potent γ-Secretase Modulators

  摘要：

  The design and the synthesis of several chemical subclasses of imidazole containing gamma-secretase modulators (GSMs) is described. Conformational restriction of pyridone 4 into bicyclic pyridone isosteres has led to compounds with high in vitro and in vivo potency. This has resulted, in the identification of benzimidazole 44a as a GSM with low nanomolar potency in vitro. In mouse, rat, and dog, this compound displayed the typical gamma-secretase modulatory profile by lowering A beta 42 and A beta 40 levels combined with an especially pronounced increase in A beta 38 and A beta 37 levels while leaving the total levels of amyloid peptides unchanged.

  DOI：

  10.1021/jm201710f

文献信息

• Discovery of novel trimethoxyphenylbenzo[d]oxazoles as dual tubulin/PDE4 inhibitors capable of inducing apoptosis at G2/M phase arrest in glioma and lung cancer cells
  作者：Jie liu、Wan Ye、Jiang-Ping Xu、Hai-Tao Wang、Xiao-Fang Li、Wen-Ya Wang、Zhong-Zhen Zhou

  DOI：10.1016/j.ejmech.2021.113700

  日期：2021.11