[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]-[2-(3-methoxyphenyl)-1-methyl-1H-benzoimidazol-4-yl]amine | 1240608-00-7

• 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: [3-methoxy-4-(4-methylimidazol-1-yl)phenyl]-[2-(3-methoxyphenyl)-1-methyl-1H-benzoimidazol-4-yl]amine
• 英文别名: N-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-2-(3-methoxyphenyl)-1-methyl-1H-benzimidazol-4-amine；N-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]-2-(3-methoxyphenyl)-1-methylbenzimidazol-4-amine
• CAS: 1240608-00-7
• 化学式: C₂₆H₂₅N₅O₂
• 分子量: 439.517
• InChiKey: FYBNSZAREGIYIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  66.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-溴-6-氟硝基苯 在 sodium dithionite 、 palladium diacetate 、 铁粉 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 作用下， 以 乙醇 、 溶剂黄146 、 甲苯 为溶剂， 反应 15.0h， 生成 [3-methoxy-4-(4-methylimidazol-1-yl)phenyl]-[2-(3-methoxyphenyl)-1-methyl-1H-benzoimidazol-4-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

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.