3-chloro-4-(1,4,5-trimethyl-1H-imidazol-2-ylsulfanyl)-phenylamine | 609347-33-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-chloro-4-(1,4,5-trimethyl-1H-imidazol-2-ylsulfanyl)-phenylamine
• 英文别名: 3-chloro-4-(1,4,5-trimethyl-1H-imidazol-2-ylsulfanyl)phenylamine；3-chloro-4-(1,4,5-trimethylimidazol-2-yl)sulfanylaniline
• CAS: 609347-33-3
• 化学式: C₁₂H₁₄ClN₃S
• 分子量: 267.782
• InChiKey: LAHBUOKVTHFLCX-UHFFFAOYSA-N

物化性质

• 沸点：
  478.8±55.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  69.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-chloro-4-(1,4,5-trimethyl-1H-imidazol-2-ylsulfanyl)-phenylamine 在 吡啶盐酸盐 、 potassium iodide 作用下， 以 乙二醇乙醚 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-[3-Chloro-4-(1,4,5-trimethyl-1H-imidazol-2-ylsulfanyl)-phenylamino]-6-methoxy-7-(3-morpholin-4-yl-propoxy)-quinoline-3-carbonitrile
  参考文献：
  名称：

  Synthesis and evaluation of 4-Anilino-6,7-dialkoxy-3-quinolinecarbonitriles as inhibitors of kinases of the Ras-MAPK signaling cascade

  摘要：

  4-[3-Chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)]anilino-6,7-diethoxy-3- quinolinecarbonitrile (3) was identified as a MEK1 kinase inhibitor with exceptional activity against LoVo cells. The structure-activity relationships of the C-4 aniline substituents were explored, and water-solubilizing groups were added at the C-7 position to improve physical properties. Secondary cellular assays revealed that a compound possessing the appropriate aniline substituents inhibited MEK1 as well as MAPK phosphorylation, thereby acting as a dual inhibitor of the Ras-MAPK signaling cascade. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00640-1
• 作为产物：
  描述：

  2-(2-Chloro-4-nitro-phenylsulfanyl)-1,4,5-trimethyl-1H-imidazole 在 铁粉 、 氯化铵 作用下， 以 甲醇 为溶剂， 生成 3-chloro-4-(1,4,5-trimethyl-1H-imidazol-2-ylsulfanyl)-phenylamine
  参考文献：
  名称：

  Synthesis and evaluation of 4-Anilino-6,7-dialkoxy-3-quinolinecarbonitriles as inhibitors of kinases of the Ras-MAPK signaling cascade

  摘要：

  4-[3-Chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)]anilino-6,7-diethoxy-3- quinolinecarbonitrile (3) was identified as a MEK1 kinase inhibitor with exceptional activity against LoVo cells. The structure-activity relationships of the C-4 aniline substituents were explored, and water-solubilizing groups were added at the C-7 position to improve physical properties. Secondary cellular assays revealed that a compound possessing the appropriate aniline substituents inhibited MEK1 as well as MAPK phosphorylation, thereby acting as a dual inhibitor of the Ras-MAPK signaling cascade. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00640-1

文献信息

• 3-Cyanoquinolines, Methods for Preparation and Use as Insulin-like Growth Factor Inhibitors
  申请人：Mayer Scott Christian

  公开号：US20090264427A1

  公开（公告）日：2009-10-22

  Imidazole-substituted 4-anilino-3-cyanoquinolines are described, which selectively inhibit IFGR kinase activity and are useful for treating disorders associated with IGFR kinases.

  描述了咪唑取代的4-苯胺基-3-氰基喹啉类化合物，其选择性抑制IGFR激酶活性，并可用于治疗与IGFR激酶相关的疾病。