8-bromo-3-methyl-2-(2-trifluoromethylphenyl)imidazo[1,2-a]pyridine | 1381869-22-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 8-bromo-3-methyl-2-(2-trifluoromethylphenyl)imidazo[1,2-a]pyridine
• 英文别名: 8-Bromo-3-methyl-2-[2-(trifluoromethyl)phenyl]imidazo[1,2-a]pyridine；8-bromo-3-methyl-2-[2-(trifluoromethyl)phenyl]imidazo[1,2-a]pyridine
• CAS: 1381869-22-2
• 化学式: C₁₅H₁₀BrF₃N₂
• 分子量: 355.157
• InChiKey: FDUHFVCJCSXUGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  17.3
• 氢给体数：
  0
• 氢受体数：
  4

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 、 8-bromo-3-methyl-2-(2-trifluoromethylphenyl)imidazo[1,2-a]pyridine 在 palladium diacetate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 以69%的产率得到[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]-[3-methyl-2-(2-trifluoromethylphenyl)imidazo[1,2-a]pyridin-8-yl]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-氨基-3-溴吡啶 、 2-溴-1-(2-三氟甲基苯基)-丙烷-1-酮 反应 0.75h， 以29%的产率得到8-bromo-3-methyl-2-(2-trifluoromethylphenyl)imidazo[1,2-a]pyridine
  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