4-methoxy-6-(3-(6-methylpyridin-2-yl)-1H-pyrazol-4-yl)quinoline

• 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: 4-methoxy-6-(3-(6-methylpyridin-2-yl)-1H-pyrazol-4-yl)quinoline
• 英文别名: 4-methoxy-6-[3-(6-methyl-pyridin-2-yl)-1H-pyrazol-4-yl]-quinoline；4-methoxy-6-[5-(6-methylpyridin-2-yl)-1H-pyrazol-4-yl]quinoline
• 化学式: C₁₉H₁₆N₄O
• 分子量: 316.362
• InChiKey: GJQBLGGPWGIDHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  63.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methoxy-6-(3-(6-methylpyridin-2-yl)-1H-pyrazol-4-yl)quinoline 、 3-bromo-N-(3-cyanophenyl)propanamide 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以39%的产率得到N-(3-cyanophenyl)-3-(4-(4-methoxyquinolin-6-yl)-3-(6-methylpyridin-2-yl)-1H-pyrazol-1-yl)propanamide
  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
• 作为产物：
  描述：

  4-甲氧基-6-氯喹啉 在 potassium tert-butylate 、 palladium diacetate 、 2-二环己膦基-2'-(N,N-二甲胺)-联苯 作用下， 以 四氢呋喃 为溶剂， 反应 22.0h， 生成 4-methoxy-6-(3-(6-methylpyridin-2-yl)-1H-pyrazol-4-yl)quinoline
  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

• Novel pyrazole compounds as transforming growth factor (TGF) inhibitors
  申请人：Pfizer Inc

  公开号：US20040116474A1

  公开（公告）日：2004-06-17

  Novel pyrazole compounds, including derivatives thereof, to intermediates for their preparation, to pharmaceutical compositions containing them and to their medicinal use are described. The compounds of the present invention are potent inhibitors of transforming growth factor (“TGF”)-&bgr; signaling pathway. They are useful in the treatment of various TGF-related disease states including, for example, cancer, and fibrotic diseases.

  本发明涉及新型吡唑化合物，包括其衍生物，以及其制备的中间体，含有它们的制药组合物和它们的药用用途。本发明的化合物是转化生长因子（“TGF”）-β信号通路的有效抑制剂。它们在治疗各种与TGF相关的疾病状态中有用，包括癌症和纤维化疾病。
• NOVEL PYRAZOLE COMPOUNDS AS TRANSFORMING GROWTH FACTOR (TGF) INHIBITORS
  申请人：Munchhof J. Michael

  公开号：US20070117850A1

  公开（公告）日：2007-05-24

  Novel pyrazole compounds, including derivatives thereof, to intermediates for their preparation, to pharmaceutical compositions containing them and to their medicinal use are described. The compounds of the present invention are potent inhibitors of transforming growth factor (“TGF”)- signaling pathway. They are useful in the treatment of various TGF-related disease states including, for example, cancer, and fibrotic diseases.

  本发明涉及新型吡唑化合物，包括其衍生物，以及其制备的中间体，含有它们的制药组合物和它们的药用用途。本发明化合物是转化生长因子（“TGF”）信号通路的有效抑制剂。它们在治疗各种TGF相关疾病状态方面非常有用，包括癌症和纤维化疾病。
• NEW PYRAZOLE DERIVATIVES AS TRANSFORMING GROWTH FACTOR (TGF) INHIBITORS
  申请人：Pfizer Products Inc.

  公开号：EP2165708A2

  公开（公告）日：2010-03-24

  Novel pyrazole compounds, including derivatives thereof, to intermediates for their preparation, to pharmaceutical compositions containing them and their medicinal use are described. The compounds of the present invention are potent inhibitors of transforming growth factor ('TGF')-β signaling pathway. They are useful in the treatment of various TGF-related disease states including, for example, cancer, and fibrotic diseases.

  本发明描述了新型吡唑化合物（包括其衍生物）、制备它们的中间体、含有它们的药物组合物及其药用用途。本发明的化合物是转化生长因子（'TGF'）-β 信号通路的强效抑制剂。它们可用于治疗各种与 TGF 相关的疾病，例如癌症和纤维化疾病。
• [EN] PYRAZOLE DERIVATIVES AS TRANSFORMING GROWTH FACTOR (TGF) INHIBITORS<br/>[FR] NOUVEAUX COMPOSES DE PYRAZOLE UTILISES COMME INHIBITEURS DU FACTEUR DE CROISSANCE TRANSFORMANT (TGF)
  申请人：PFIZER PROD INC

  公开号：WO2004026306A3

  公开（公告）日：2004-07-01
• METHOD FOR PRODUCING RETINAL PIGMENT EPITHELIAL CELLS
  申请人：Pfizer Limited

  公开号：EP3080248A1

  公开（公告）日：2016-10-19