5-bromo-2-(4-methoxyphenyl)benzo[d]oxazole | 1107023-88-0

• 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-bromo-2-(4-methoxyphenyl)benzo[d]oxazole
• 英文别名: 5-Bromo-2-(4-methoxyphenyl)-1,3-benzoxazole
• CAS: 1107023-88-0
• 化学式: C₁₄H₁₀BrNO₂
• 分子量: 304.143
• InChiKey: NVPNBTYGIGRZES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-bromo-2-(4-methoxyphenyl)benzo[d]oxazole 在 氯化亚砜 、 palladium diacetate 、 N,N-二甲基甲酰胺 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 乙二醇二甲醚 、 甲苯 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Decreasing HepG2 Cytotoxicity by Lowering the Lipophilicity of Benzo[d]oxazolephosphinate Ester Utrophin Modulators

  摘要：

  Utrophin modulation is a disease-modifying therapeutic strategy for Duchenne muscular dystrophy that would be applicable to all patient populations. To improve the suboptimal profile of ezutromid, the first-in-class clinical candidate, a second generation of utrophin modulators bearing a phosphinate ester moiety was developed. This modification significantly improved the physicochemical and ADME properties, but one of the main lead molecules was found to have dose-limiting hepatotoxicity. In this work we describe how less lipophilic analogues retained utrophin modulatory activity in a reporter gene assay, upregulated utrophin protein in dystrophic mouse muscle cells, but also had improved physicochemical and ADME properties. Notably, ClogP was found to directly correlate with pIC50 in HepG2 cells, hence leading to a potentially safer toxicological profiles in this series. Compound 21 showed a balanced profile (H2K EC50: 4.17 μM, solubility: 477 μM, mouse hepatocyte T 1/2 > 240 min) and increased utrophin protein 1.6-fold in a Western blot assay.

  DOI：

  10.1021/acsmedchemlett.0c00405
• 作为产物：
  描述：

  N-(4-bromo)-phenoxyphtalimide 在 氧气 、 copper(II) bis(trifluoromethanesulfonate) 、 溶剂黄146 、 肼 作用下， 以 甲醇 、 氯仿 、 水 、 甲苯 为溶剂， 反应 14.0h， 生成 5-bromo-2-(4-methoxyphenyl)benzo[d]oxazole
  参考文献：
  名称：

  Copper-Mediated Synthesis of Substituted 2-Aryl-N-benzylbenzimidazoles and 2-Arylbenzoxazoles via C–H Functionalization/C–N/C–O Bond Formation

  摘要：

  An efficient method for the transformation of N-benzyl bisarylhydrazones and bisaryloxime ethers to functionalized 2-aryl-N-benzylbenzimidazoles and 2-arylbenzoxazoles is described. The protocol involves a copper(II)-mediated cascade C-H functionalization/C-N/C-O bond formation under neutral conditions. Substrates having either electron-donating or -withdrawing substituents undergo the cyclization to afford the target heterocycles at moderate temperature.

  DOI：

  10.1021/jo2005632