[2-(4-fluorophenyl)-1H-benzoimidazol-4-yl]-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]amine | 1240608-19-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: [2-(4-fluorophenyl)-1H-benzoimidazol-4-yl]-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]amine
• 英文别名: 2-(4-fluorophenyl)-N-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-1H-benzimidazol-4-amine；2-(4-fluorophenyl)-N-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]-1H-benzimidazol-4-amine
• CAS: 1240608-19-8
• 化学式: C₂₄H₂₀FN₅O
• 分子量: 413.454
• InChiKey: PCAZIKURHILOSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-甲氧基-4-(4-甲基-1H-咪唑-1-基)苯胺 在 硫酸 、 10% Pd/C 、 氢气 、 palladium diacetate 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium nitrite 作用下， 以 甲醇 、 溶剂黄146 、 甲苯 为溶剂， 反应 1.5h， 生成 [2-(4-fluorophenyl)-1H-benzoimidazol-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

文献信息

• NOVEL SUBSTITUTED BENZOXAZOLE, BENZIMIDAZOLE, OXAZOLOPYRIDINE AND IMIDAZOPYRIDINE DERIVATIVES AS GAMMA SECRETASE MODULATORS
  申请人：Janssen Pharmaceuticals, Inc.

  公开号：EP2398793B1

  公开（公告）日：2013-12-18
• US8772504B2
  申请人：——

  公开号：US8772504B2

  公开（公告）日：2014-07-08
• Design and Synthesis of a Novel Series of Bicyclic Heterocycles As Potent γ-Secretase Modulators
  作者：Francois Bischoff、Didier Berthelot、Michel De Cleyn、Gregor Macdonald、Garrett Minne、Daniel Oehlrich、Serge Pieters、Michel Surkyn、Andrés A. Trabanco、Gary Tresadern、Sven Van Brandt、Ingrid Velter、Mirko Zaja、Herman Borghys、Chantal Masungi、Marc Mercken、Harrie J. M. Gijsen

  DOI：10.1021/jm201710f

  日期：2012.11.8

  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.