3-Methyl-4-(1-methylimidazol-2-yl)sulfanylaniline | 609347-30-0

• 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-Methyl-4-(1-methylimidazol-2-yl)sulfanylaniline
• CAS: 609347-30-0
• 化学式: C₁₁H₁₃N₃S
• 分子量: 219.31
• InChiKey: LUTIKCCUMLOKQQ-UHFFFAOYSA-N

物化性质

• 沸点：
  427.0±55.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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-Methyl-4-(1-methylimidazol-2-yl)sulfanylaniline 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 6-Methoxy-4-[3-methyl-4-(1-methyl-1H-imidazol-2-ylsulfanyl)-phenylamino]-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：

  1-Methyl-2-(2-methyl-4-nitro-phenylsulfanyl)-1H-imidazole 在 铁粉 、 氯化铵 作用下， 以 甲醇 为溶剂， 生成 3-Methyl-4-(1-methylimidazol-2-yl)sulfanylaniline
  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

• Synthesis and evaluation of 4-Anilino-6,7-dialkoxy-3-quinolinecarbonitriles as inhibitors of kinases of the Ras-MAPK signaling cascade
  作者：Dan Berger、Minu Dutia、Dennis Powell、Biqi Wu、Allan Wissner、Diane H. Boschelli、M.Brawner Floyd、Nan Zhang、Nancy Torres、Jeremy Levin、Xuemei Du、Donald Wojciechowicz、Carolyn Discafani、Constance Kohler、Steven C. Kim、Larry R. Feldberg、Karen Collins、Robert Mallon

  DOI：10.1016/s0960-894x(03)00640-1

  日期：2003.9

  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.