2-methyl-6-(4-phenyl-1H-1,2,3-triazol-1-yl)pyridine | 1224886-20-7

• 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-methyl-6-(4-phenyl-1H-1,2,3-triazol-1-yl)pyridine
• 英文别名: 2-Methyl-6-(4-phenyltriazol-1-yl)pyridine；2-methyl-6-(4-phenyltriazol-1-yl)pyridine
• CAS: 1224886-20-7
• 化学式: C₁₄H₁₂N₄
• 分子量: 236.276
• InChiKey: OPPFLIRUHQNIJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-溴喹喔啉 、 2-methyl-6-(4-phenyl-1H-1,2,3-triazol-1-yl)pyridine 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 23.0h， 以14%的产率得到6-[3-(6-Methylpyridin-2-yl)-5-phenyltriazol-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 sodium azide 、 sodium L-ascorbate 、 碳酸氢钠 、 copper(II) sulfate 作用下， 以 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 73.0h， 生成 2-methyl-6-(4-phenyl-1H-1,2,3-triazol-1-yl)pyridine
  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

• Fused Tetrazoles as Azide Surrogates in Click Reaction: Efficient Synthesis of N-Heterocycle-Substituted 1,2,3-Triazoles
  作者：Buddhadeb Chattopadhyay、Claudia I. Rivera Vera、Stepan Chuprakov、Vladimir Gevorgyan

  DOI：10.1021/ol100745d

  日期：2010.5.7

  It has been shown that various pyrido-, quinolino-, pyrazino-, and quinoxalinotetrazoles can be used efficiently as azide components in Cu-catalyzed click reaction with alkynes. This method allows for efficient synthesis of a wide variety of N-heterocyclic derivatives of 1,2,3-triazoles.

  研究表明，各种吡啶并、喹啉、吡嗪和喹喔啉四唑可以有效地用作铜催化与炔烃的点击反应中的叠氮化物组分。该方法可以有效合成多种 1,2,3-三唑 N-杂环衍生物。