2-[4-(2,3-dimethylquinoxalin-6-yl)-3-(6-methylpyridin-2-yl)-1H-pyrazol-1-yl]-N-phenylacetamide | 1334763-89-1

• 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: 2-[4-(2,3-dimethylquinoxalin-6-yl)-3-(6-methylpyridin-2-yl)-1H-pyrazol-1-yl]-N-phenylacetamide
• 英文别名: 2-[4-(2,3-dimethylquinoxalin-6-yl)-3-(6-methylpyridin-2-yl)pyrazol-1-yl]-N-phenylacetamide
• CAS: 1334763-89-1
• 化学式: C₂₇H₂₄N₆O
• 分子量: 448.527
• InChiKey: STWGGWFROPAXHA-UHFFFAOYSA-N

物化性质

• 熔点：
  227.9 °C
• 沸点：
  653.9±55.0 °C(predicted)
• 密度：
  1.26±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  85.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[4-(2,3-dimethylquinoxalin-6-yl)-3-(6-methylpyridin-2-yl)-1H-pyrazol-1-yl]-N-phenylacetamide 在 劳森试剂 作用下， 以 乙二醇二甲醚 为溶剂， 反应 12.0h， 以24%的产率得到2-[4-(2,3-dimethylquinoxalin-6-yl)-3-(6-methylpyridin-2-yl)-1H-pyrazol-1-yl]-N-phenylethanethioamide
  参考文献：
  名称：

  Synthesis and biological evaluation of 1-substituted-3(5)-(6-methylpyridin-2-yl)-4-(quinoxalin-6-yl)pyrazoles as transforming growth factor-β type 1 receptor kinase inhibitors

  摘要：

  A series of 1-substituted-3(5)-(6-methylpyridin-2-yl)-4-(quinoxalin-6-yl)pyrazoles 14a-d, 15a-d, 17a, 17b, 18a-d, 19a, and 19b has been synthesized and evaluated for their ALK5 inhibitory activity in an enzyme assay and in a cell-based luciferase reporter assay. The 2-[3-(6-methylpyridin-2-yl)-4-(quinoxalin-6-yl)-1H-pyrazol-1-yl]-N-phenylethanethioamide (18a) inhibited ALK5 phosphorylation with an IC50 value of 0.013 mu M and showed 80% inhibition at 0.1 mu M in a luciferase reporter assay using HaCaT cells permanently transfected with p3TP-luc reporter construct. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.063
• 作为产物：
  描述：

  2,3-dimethylquinoxaline-6-carbaldehyde 在 sodium hydride 、 caesium carbonate 、 溶剂黄146 、 sodium iodide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 25.0h， 生成 2-[4-(2,3-dimethylquinoxalin-6-yl)-5-(6-methylpyridin-2-yl)-1H-pyrazol-1-yl]-N-phenylacetamide 、 2-[4-(2,3-dimethylquinoxalin-6-yl)-3-(6-methylpyridin-2-yl)-1H-pyrazol-1-yl]-N-phenylacetamide
  参考文献：
  名称：

  Synthesis and biological evaluation of 1-substituted-3(5)-(6-methylpyridin-2-yl)-4-(quinoxalin-6-yl)pyrazoles as transforming growth factor-β type 1 receptor kinase inhibitors

  摘要：

  A series of 1-substituted-3(5)-(6-methylpyridin-2-yl)-4-(quinoxalin-6-yl)pyrazoles 14a-d, 15a-d, 17a, 17b, 18a-d, 19a, and 19b has been synthesized and evaluated for their ALK5 inhibitory activity in an enzyme assay and in a cell-based luciferase reporter assay. The 2-[3-(6-methylpyridin-2-yl)-4-(quinoxalin-6-yl)-1H-pyrazol-1-yl]-N-phenylethanethioamide (18a) inhibited ALK5 phosphorylation with an IC50 value of 0.013 mu M and showed 80% inhibition at 0.1 mu M in a luciferase reporter assay using HaCaT cells permanently transfected with p3TP-luc reporter construct. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.063

文献信息

• Synthesis and biological evaluation of 1-substituted-3(5)-(6-methylpyridin-2-yl)-4-(quinoxalin-6-yl)pyrazoles as transforming growth factor-β type 1 receptor kinase inhibitors
  作者：Cheng Hua Jin、Domalapally Sreenu、Maddeboina Krishnaiah、Vura Bala Subrahmanyam、Kota Sudhakar Rao、Annaji Venkata Nagendra Mohan、Chul-Yong Park、Jee-Yeon Son、Do-Hyun Son、Hyun-Ju Park、Yhun Yhong Sheen、Dae-Kee Kim

  DOI：10.1016/j.ejmech.2011.05.063

  日期：2011.9

  A series of 1-substituted-3(5)-(6-methylpyridin-2-yl)-4-(quinoxalin-6-yl)pyrazoles 14a-d, 15a-d, 17a, 17b, 18a-d, 19a, and 19b has been synthesized and evaluated for their ALK5 inhibitory activity in an enzyme assay and in a cell-based luciferase reporter assay. The 2-[3-(6-methylpyridin-2-yl)-4-(quinoxalin-6-yl)-1H-pyrazol-1-yl]-N-phenylethanethioamide (18a) inhibited ALK5 phosphorylation with an IC50 value of 0.013 mu M and showed 80% inhibition at 0.1 mu M in a luciferase reporter assay using HaCaT cells permanently transfected with p3TP-luc reporter construct. (C) 2011 Elsevier Masson SAS. All rights reserved.