8-bromo-2-(3-methoxyphenyl)imidazo[1,2-a]pyridine | 1381869-20-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 8-bromo-2-(3-methoxyphenyl)imidazo[1,2-a]pyridine
• 英文别名: 8-Bromo-2-(3-methoxyphenyl)imidazo[1,2-a]pyridine
• CAS: 1381869-20-0
• 化学式: C₁₄H₁₁BrN₂O
• mdl: MFCD25691252
• 分子量: 303.158
• InChiKey: FDDLCUVDTUVUBG-UHFFFAOYSA-N

物化性质

• 密度：
  1.47±0.1 g/cm3(Predicted)

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：
  0.071
• 拓扑面积：
  26.5
• 氢给体数：
  0
• 氢受体数：
  2

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-2-(3-methoxyphenyl)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50%的产率得到[2-(3-methoxyphenyl)imidazo[1,2-a]pyridin-8-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：

  2-氨基-3-溴吡啶 、 2-溴-3‘-甲氧基苯乙酮 生成 8-bromo-2-(3-methoxyphenyl)imidazo[1,2-a]pyridine
  参考文献：
  名称：

  Identification of novel SIRT1 activators endowed with cardioprotective profile

  摘要：

  DOI：

  10.1016/j.ejps.2021.105930

文献信息

• Progress in the Field of Aldehyde Dehydrogenase Inhibitors: Novel Imidazo[1,2-<i>a</i>]pyridines against the 1A Family
  作者：Luca Quattrini、Edoardo Luigi Maria Gelardi、Giovanni Petrarolo、Giorgia Colombo、Davide Maria Ferraris、Francesca Picarazzi、Menico Rizzi、Silvia Garavaglia、Concettina La Motta

  DOI：10.1021/acsmedchemlett.9b00686

  日期：2020.5.14

  the aldehyde dehydrogenase 1A family are commonly acknowledged as hallmarks of cancer stem cells, and their overexpression is significantly associated with poor prognosis in different types of malignancies. Accordingly, treatments targeting these enzymes may represent a successful strategy to fight cancer. In this work we describe a novel series of imidazo[1,2-a]pyridines, designed as aldehyde dehydrogenase

  醛脱氢酶1A家族成员通常被认为是癌症干细胞的标志，它们的过表达与不同类型恶性肿瘤的不良预后显着相关。因此，靶向这些酶的治疗可能代表抗击癌症的成功策略。在这项工作中，我们描述了一系列新的咪唑并[1,2-a]吡啶，它们是通过先前开发的铅的基于结构的优化设计为醛脱氢酶抑制剂的。在体外评估了新化合物对ALDH1A家族的三种同工型的活性和选择性，并通过结晶和模型研究研究了它们与1A3同工型催化位点相互作用的能力。
• 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.
• Identification of novel SIRT1 activators endowed with cardioprotective profile
  作者：Lorenzo Flori、Giovanni Petrarolo、Simone Brogi、Concettina La Motta、Lara Testai、Vincenzo Calderone

  DOI：10.1016/j.ejps.2021.105930

  日期：2021.10