6-[5-(4-Methoxyphenyl)-3-(6-methylpyridin-2-yl)triazol-4-yl]quinoxaline | 1422465-17-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-[5-(4-Methoxyphenyl)-3-(6-methylpyridin-2-yl)triazol-4-yl]quinoxaline
• 英文别名: 6-[5-(4-methoxyphenyl)-3-(6-methylpyridin-2-yl)triazol-4-yl]quinoxaline
• CAS: 1422465-17-5
• 化学式: C₂₃H₁₈N₆O
• 分子量: 394.436
• InChiKey: JPNYZZXKJCEFSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  78.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-溴-6-甲基吡啶 在 sodium azide 、 sodium L-ascorbate 、 四丁基醋酸铵 、 palladium diacetate 、 碳酸氢钠 、 copper(II) sulfate 作用下， 以 N-甲基吡咯烷酮 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 61.0h， 生成 6-[5-(4-Methoxyphenyl)-3-(6-methylpyridin-2-yl)triazol-4-yl]quinoxaline
  参考文献：
  名称：

  Synthesis and biological evaluation of 1-(6-methylpyridin-2-yl)-5-(quinoxalin-6-yl)-1,2,3-triazoles as transforming growth factor-β type 1 receptor kinase inhibitors

  摘要：

  A series of 1-(6-methylpyridin-2-yl)-5-(quinoxalin-6-yl)-1,2,3-triazoles has been synthesized and evaluated for their ALK5 inhibitory activity. The 1-(6-methylpyridin-2-yl)-1,2,3-triazoles were assembled by Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition. Following this, quinoxaline was introduced through Pd-catalyzed direct arylation. The synthesized 1-(6-methylpyridin-2-yl)-5-(quinoxalin-6-yl)-1,2,3-triazoles revealed significant selectivity differences with respect to p38 alpha MAP kinase. In particular, 12k showed 80.8% ALK5 inhibitory activity at a concentration of 10 mu M and IC50 value of 4.69 mu M, but did not show p38 alpha MAP kinase inhibitory activity (-1.94% inhibition at a concentration of 10 mu M). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.12.008

文献信息

• Synthesis and biological evaluation of 1-(6-methylpyridin-2-yl)-5-(quinoxalin-6-yl)-1,2,3-triazoles as transforming growth factor-β type 1 receptor kinase inhibitors
  作者：Fei Li、Yunjeong Park、Jung-Mi Hah、Jae-Sang Ryu

  DOI：10.1016/j.bmcl.2012.12.008

  日期：2013.2

  A series of 1-(6-methylpyridin-2-yl)-5-(quinoxalin-6-yl)-1,2,3-triazoles has been synthesized and evaluated for their ALK5 inhibitory activity. The 1-(6-methylpyridin-2-yl)-1,2,3-triazoles were assembled by Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition. Following this, quinoxaline was introduced through Pd-catalyzed direct arylation. The synthesized 1-(6-methylpyridin-2-yl)-5-(quinoxalin-6-yl)-1,2,3-triazoles revealed significant selectivity differences with respect to p38 alpha MAP kinase. In particular, 12k showed 80.8% ALK5 inhibitory activity at a concentration of 10 mu M and IC50 value of 4.69 mu M, but did not show p38 alpha MAP kinase inhibitory activity (-1.94% inhibition at a concentration of 10 mu M). (C) 2012 Elsevier Ltd. All rights reserved.