6-[2-benzyl-5-(6-methylpyridin-2-yl)-1H-imidazol-4-yl]quinoxaline | 1145871-52-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 6-[2-benzyl-5-(6-methylpyridin-2-yl)-1H-imidazol-4-yl]quinoxaline
• CAS: 1145871-52-8
• 化学式: C₂₄H₁₉N₅
• 分子量: 377.448
• InChiKey: IVLXFWQMPDDVHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  67.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-[2-benzyl-5-(6-methylpyridin-2-yl)-1H-imidazol-4-yl]quinoxaline 在 氯磺酸 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and biological evaluation of benzenesulfonamide-substituted 4-(6-alkylpyridin-2-yl)-5-(quinoxalin-6-yl)imidazoles as transforming growth factor-β type 1 receptor kinase inhibitors

  摘要：

  A series of benzenesulfonamide-substituted 4-(6-alkylpyridin-2-yl)-5-(quinoxalin-6-yl)imidazoles (15a-1) have been synthesized and evaluated for their ALK5 inhibitory activity in cell-based luciferase reporter assays. Among them, 4-[5-(6-methylpyridin-2-yl)-4-(quinoxalin-6-yl)-1H-imidazol-2-ylmethyl]benzenesulfonamide (15b) and 4-[5-(6-ethylpyridin-2-yl)-4-(quinoxalin-6-yl)-1H-imidazol-2-ylmethyl]benzene-sulfonamide (15c) showed more than 90% inhibition at 0.5 mu M in a luciferase reporter assay using HaCaT cells transiently transfected with p3TP-luc reporter construct, but inhibited p38 alpha MAP kinase activity only 11 and 8% at a concentration of 10 mu M, respectively. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.03.024
• 作为产物：
  描述：

  1-(6-methylpyridin-2-yl)-2-(quinoxalin-6-yl)ethane-1,2-dione 、 苯乙醛 在 ammonium acetate 作用下， 以 甲醇 、 甲基叔丁基醚 为溶剂， 反应 2.0h， 以25%的产率得到6-[2-benzyl-5-(6-methylpyridin-2-yl)-1H-imidazol-4-yl]quinoxaline
  参考文献：
  名称：

  Synthesis and biological evaluation of benzenesulfonamide-substituted 4-(6-alkylpyridin-2-yl)-5-(quinoxalin-6-yl)imidazoles as transforming growth factor-β type 1 receptor kinase inhibitors

  摘要：

  A series of benzenesulfonamide-substituted 4-(6-alkylpyridin-2-yl)-5-(quinoxalin-6-yl)imidazoles (15a-1) have been synthesized and evaluated for their ALK5 inhibitory activity in cell-based luciferase reporter assays. Among them, 4-[5-(6-methylpyridin-2-yl)-4-(quinoxalin-6-yl)-1H-imidazol-2-ylmethyl]benzenesulfonamide (15b) and 4-[5-(6-ethylpyridin-2-yl)-4-(quinoxalin-6-yl)-1H-imidazol-2-ylmethyl]benzene-sulfonamide (15c) showed more than 90% inhibition at 0.5 mu M in a luciferase reporter assay using HaCaT cells transiently transfected with p3TP-luc reporter construct, but inhibited p38 alpha MAP kinase activity only 11 and 8% at a concentration of 10 mu M, respectively. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.03.024

文献信息

• Synthesis and biological evaluation of benzenesulfonamide-substituted 4-(6-alkylpyridin-2-yl)-5-(quinoxalin-6-yl)imidazoles as transforming growth factor-β type 1 receptor kinase inhibitors
  作者：Dae-Kee Kim、Sun Hee Jung、Ho Soon Lee、Purushottam M. Dewang

  DOI：10.1016/j.ejmech.2008.03.024

  日期：2009.2

  A series of benzenesulfonamide-substituted 4-(6-alkylpyridin-2-yl)-5-(quinoxalin-6-yl)imidazoles (15a-1) have been synthesized and evaluated for their ALK5 inhibitory activity in cell-based luciferase reporter assays. Among them, 4-[5-(6-methylpyridin-2-yl)-4-(quinoxalin-6-yl)-1H-imidazol-2-ylmethyl]benzenesulfonamide (15b) and 4-[5-(6-ethylpyridin-2-yl)-4-(quinoxalin-6-yl)-1H-imidazol-2-ylmethyl]benzene-sulfonamide (15c) showed more than 90% inhibition at 0.5 mu M in a luciferase reporter assay using HaCaT cells transiently transfected with p3TP-luc reporter construct, but inhibited p38 alpha MAP kinase activity only 11 and 8% at a concentration of 10 mu M, respectively. (C) 2008 Elsevier Masson SAS. All rights reserved.