7-chloro-2-(2,4-difluorophenyl)-3-methyl-2H-indazole | 1381869-37-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 7-chloro-2-(2,4-difluorophenyl)-3-methyl-2H-indazole
• 英文别名: 7-Chloro-2-(2,4-difluorophenyl)-3-methylindazole；7-chloro-2-(2,4-difluorophenyl)-3-methylindazole
• CAS: 1381869-37-9
• 化学式: C₁₄H₉ClF₂N₂
• 分子量: 278.689
• InChiKey: KMYOLAYIZXHKAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  17.8
• 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 、 7-chloro-2-(2,4-difluorophenyl)-3-methyl-2H-indazole 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62%的产率得到[2-(2,4-difluorophenyl)-3-methyl-2H-indazol-7-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：

  3-氯-2-硝基苯甲醛 在 tin(II) chloride dihdyrate 、 三乙酰氧基硼氢化钠 、 溶剂黄146 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 19.08h， 生成 7-chloro-2-(2,4-difluorophenyl)-3-methyl-2H-indazole
  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