5-bromo-2-(4-methylimidazol-1-yl)pyridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-bromo-2-(4-methylimidazol-1-yl)pyridine
• 英文别名: Pyridine, 5-bromo-2-(4-methyl-1H-imidazol-1-yl)-
• 化学式: C₉H₈BrN₃
• 分子量: 238.087
• InChiKey: ZZJHQPQEIHWUBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-bromo-2-(4-methylimidazol-1-yl)pyridine 在 copper(I) oxide 、 氨 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以12%的产率得到6-(4-methyl-1H-imidazol-1-yl)pyridin-3-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：

  2,5-二溴吡啶 、 4-甲基咪唑 在 potassium carbonate 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 16.0h， 以62%的产率得到5-bromo-2-(4-methylimidazol-1-yl)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

文献信息

• Synthesis and antibacterial activity of oxazolidinones containing pyridine substituted with heteroaromatic ring
  作者：Yeong Woo Jo、Weon Bin Im、Jae Keol Rhee、Mi Ja Shim、Won Bae Kim、Eung Chil Choi

  DOI：10.1016/j.bmc.2004.08.025

  日期：2004.11

  group of linezolid was replaced with heteroaromatic ring substituted pyridine moiety, were newly synthesized, and their substituted effects on in vitro and in vivo antibacterial activities were evaluated against four problematic gram-positive strains including drug resistant strains and two gram-negative strains. Most compounds exhibited the enhanced in vitro activities with 4-16-fold and three compounds

  新合成了一系列恶唑烷酮衍生物，其中的利奈唑胺的吗啉代基团被杂芳环取代的吡啶部分取代，并评估了它们对四种有问题的革兰氏阳性菌株的体外和体内抗菌活性的取代作用，包括耐药菌株和两个革兰氏阴性菌株。大多数化合物具有4-16倍的增强的体外活性，三种化合物的体内功效比利奈唑胺高2倍以上。
• 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.