N-(3-cyanophenyl)-2-(4-(4-methoxyquinolin-6-yl)-3-(6-methylpyridin-2-yl)-1H-pyrazol-1-yl)acetamide | 1308760-93-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-(3-cyanophenyl)-2-(4-(4-methoxyquinolin-6-yl)-3-(6-methylpyridin-2-yl)-1H-pyrazol-1-yl)acetamide
• 英文别名: N-(3-cyanophenyl)-2-[4-(4-methoxyquinolin-6-yl)-3-(6-methylpyridin-2-yl)pyrazol-1-yl]acetamide
• CAS: 1308760-93-1
• 化学式: C₂₈H₂₂N₆O₂
• 分子量: 474.522
• InChiKey: AFVKISLMRSPHQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-甲氧基-6-氯喹啉 在 potassium tert-butylate 、 palladium diacetate 、 sodium hydride 、 sodium iodide 、 2-二环己膦基-2'-(N,N-二甲胺)-联苯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.5h， 生成 N-(3-cyanophenyl)-2-(4-(4-methoxyquinolin-6-yl)-5-(6-methylpyridin-2-yl)-1H-pyrazol-1-yl)acetamide 、 N-(3-cyanophenyl)-2-(4-(4-methoxyquinolin-6-yl)-3-(6-methylpyridin-2-yl)-1H-pyrazol-1-yl)acetamide
  参考文献：
  名称：

  Synthesis and biological evaluation of 1-substituted-3(5)-(6-methylpyridin-2-yl)-4-(quinolin-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-(quinolin-6-yl)pyrazoles 14a-e, 15a-e, 17a-c, and 18a-d have been synthesized and evaluated for their ALK5 inhibitory activity in an enzyme assay and in a cell-based luciferase reporter assay. The 6-quinolinyl pyrazole analogue 14b inhibited ALK5 phosphorylation with IC50 value of 0.022 mu M and showed 84% inhibition at 0.1 mu M in a luciferase reporter assay using HaCaT cells permanently transfected with p3TP-luc reporter construct. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.03.008

文献信息

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

  DOI：10.1016/j.bmc.2011.03.008

  日期：2011.4

  A series of 1-substituted-3(5)-(6-methylpyridin-2-yl)-4-(quinolin-6-yl)pyrazoles 14a-e, 15a-e, 17a-c, and 18a-d have been synthesized and evaluated for their ALK5 inhibitory activity in an enzyme assay and in a cell-based luciferase reporter assay. The 6-quinolinyl pyrazole analogue 14b inhibited ALK5 phosphorylation with IC50 value of 0.022 mu M and showed 84% inhibition at 0.1 mu M in a luciferase reporter assay using HaCaT cells permanently transfected with p3TP-luc reporter construct. (C) 2011 Elsevier Ltd. All rights reserved.