1-(6-methylpyridin-2-yl)-2-(quinolin-6-yl)ethanone | 476472-48-7

• 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: 1-(6-methylpyridin-2-yl)-2-(quinolin-6-yl)ethanone
• 英文别名: 1-(6-Methyl-pyridin-2-yl)-2-quinolin-6-yl-ethanone；1-(6-methylpyridin-2-yl)-2-quinolin-6-ylethanone
• CAS: 476472-48-7
• 化学式: C₁₇H₁₄N₂O
• 分子量: 262.311
• InChiKey: UFHMNJKABGHUOC-UHFFFAOYSA-N

物化性质

• 沸点：
  445.9±35.0 °C(Predicted)
• 密度：
  1.200±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  42.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(6-methylpyridin-2-yl)-2-(quinolin-6-yl)ethanone 在 劳森试剂 、 caesium carbonate 作用下， 以 乙二醇二甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 3-(3-(6-methylpyridin-2-yl)-4-(quinolin-6-yl)-1H-pyrazol-1-yl)-N-phenylpropanethioamide
  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：

  2-乙酰基-6-甲基吡啶 、 6-氯喹啉 在 palladium diacetate 、 2-二环己膦基-2'-(N,N-二甲胺)-联苯 potassium tert-butylate 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以78%的产率得到1-(6-methylpyridin-2-yl)-2-(quinolin-6-yl)ethanone
  参考文献：
  名称：

  [EN] NOVEL TRIAZOLE AND OXAZOLE COMPOUNDS AS TRANSFORMING GROWTH FACTOR (TGF) INHIBITOR
  [FR] NOUVEAUX COMPOSES DE TRIAZOLE ET D'OXAZOLE, INHIBITEURS DU FACTEUR DE CROISSANCE TRANSFORMANT

  摘要：

  描述了公式I a - c的新噻唑衍生物，其制备的中间体，含有它们的药物组合物以及它们的药用。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相关的疾病状态中非常有用，例如癌症和纤维化疾病。

  公开号：

  WO2004026863A1

文献信息

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

  公开号：US20040176390A1

  公开（公告）日：2004-09-09

  Novel fused heteroaromatic 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.

  描述了新型融合杂芳化合物，包括其衍生物，以及用于其制备的中间体，含有它们的药物组合物以及它们的药用。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相关的疾病状态中非常有用，包括癌症和纤维化疾病。
• Synthesis and biological evaluation of 4(5)-(6-methylpyridin-2-yl)imidazoles and -pyrazoles as transforming growth factor-β type 1 receptor kinase inhibitors
  作者：Dae-Kee Kim、Yeon-Im Lee、Yeon Woo Lee、Purushottam M. Dewang、Yhun Yhong Sheen、Yeo Woon Kim、Hyun-Ju Park、Jakyung Yoo、Ho Soon Lee、Yong-Kook Kim

  DOI：10.1016/j.bmc.2010.04.071

  日期：2010.6.15

  A series of 4(5)-(6-methylpyridin-2-yl)imidazoles 16–19 and -pyrazoles 22–29, 33, and 34 have been synthesized and evaluated for their ALK5 inhibitory activity in an enzyme assay and in cell-based luciferase reporter assays. The 6-quinolinyl imidazole analogs 16 and 18 inhibited ALK5 phosphorylation with IC50 values of 0.026 and 0.034 μM, respectively. In a luciferase reporter assay using HaCaT cells

  一系列的4（5） - （6-甲基吡啶-2-基）咪唑类16-19和-pyrazoles 22-29，33和34都在酶测定法和细胞中被合成并评价了它们的ALK5抑制活性基于荧光素酶报告基因的检测。6-喹啉基咪唑类似物16和18抑制ALK5磷酸化，IC 50值分别为0.026和0.034μM。在使用p3TP-luc报告基因构建体瞬时转染的HaCaT细胞进行的荧光素酶报告基因分析中，18个在0.05μM时显示66％的抑制，而竞争化合物2和3在显示44％时被抑制。的绑定方式18通过柔性对接研究与ALK5生成：18复杂的显示，它通过形成广泛的和紧密的相互作用很符合ALK5的活性位点空腔。
• Novel oxazole and thiazole compounds as transforming growth factor (TGF) inhibitors
  申请人：Pfizer Inc

  公开号：US20040110797A1

  公开（公告）日：2004-06-10

  Novel oxazole and thiazole 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.

  本发明涉及新型噁唑和噻唑化合物，包括其衍生物，以及制备它们的中间体，含有它们的制药组合物以及它们的药用用途。本发明所述化合物是转化生长因子（“TGF”）-β信号通路的有效抑制剂。它们可用于治疗各种与TGF相关的疾病状态，包括例如癌症和纤维化疾病。
• Oxazole and thiazole compounds as transforming growth factor (TGF) inhibitors
  申请人：Pfizer Inc.

  公开号：US07273936B2

  公开（公告）日：2007-09-25

  Novel oxazole and thiazole 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”)-β signaling pathway. They are useful in the treatment of various TGF-related disease states including, for example, cancer and fibrotic diseases.

  本发明涉及新型噁唑和噻唑化合物，包括其衍生物，以及它们的制备中间体，含有它们的制药组合物和它们的药用用途。本发明的化合物是强效的转化生长因子（“TGF”）-β信号通路抑制剂。它们可用于治疗各种与TGF相关的疾病状态，包括癌症和纤维化疾病。
• NOVEL FUSED HETEROAROMATIC COMPOUNDS AS TRANSFORMING GROWTH FACTOR (TGF) INHIBITORS
  申请人：Blumberg Laura C.

  公开号：US20080275235A1

  公开（公告）日：2008-11-06

  Novel fused heteroaromatic 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.

  本发明涉及融合的杂环化合物，包括其衍生物，以及制备它们的中间体，含有它们的制药组合物以及它们的药用用途。本发明的化合物是转化生长因子（“TGF”）信号通路的有效抑制剂。它们在治疗各种与TGF相关的疾病状态方面非常有用，包括癌症和纤维化疾病等。