2-(4-(3,5-dimethoxyphenyl)-1H-1,2,3-triazol-1-yl)-6-methylpyridine | 1422465-04-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(4-(3,5-dimethoxyphenyl)-1H-1,2,3-triazol-1-yl)-6-methylpyridine
• 英文别名: 2-[4-(3,5-Dimethoxyphenyl)triazol-1-yl]-6-methylpyridine；2-[4-(3,5-dimethoxyphenyl)triazol-1-yl]-6-methylpyridine
• CAS: 1422465-04-0
• 化学式: C₁₆H₁₆N₄O₂
• 分子量: 296.329
• InChiKey: YINLJZXHPXHVGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  62.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-溴喹喔啉 、 2-(4-(3,5-dimethoxyphenyl)-1H-1,2,3-triazol-1-yl)-6-methylpyridine 在 四丁基醋酸铵 、 palladium diacetate 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 9.0h， 以12%的产率得到6-[5-(3,5-Dimethoxyphenyl)-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
• 作为产物：
  描述：

  2-溴-6-甲基吡啶 在 copper(l) iodide 、 sodium azide 、 N,N-二异丙基乙胺 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.0h， 生成 2-(4-(3,5-dimethoxyphenyl)-1H-1,2,3-triazol-1-yl)-6-methylpyridine
  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