6-bromo-N4-(4-fluorophenyl)quinoline-3,4-diamine | 853910-68-6

• 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: 6-bromo-N4-(4-fluorophenyl)quinoline-3,4-diamine
• 英文别名: 6-bromo-4-N-(4-fluorophenyl)quinoline-3,4-diamine
• CAS: 853910-68-6
• 化学式: C₁₅H₁₁BrFN₃
• 分子量: 332.175
• InChiKey: XRXMKJVZLCSALQ-UHFFFAOYSA-N

物化性质

• 沸点：
  443.0±45.0 °C(Predicted)
• 密度：
  1.616±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-bromo-N4-(4-fluorophenyl)quinoline-3,4-diamine 在 溶剂黄146 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 0.5h， 生成 8-bromo-1-(4-fluorophenyl)-1H-[1,2,3]triazolo[4,5-c]quinoline
  参考文献：
  名称：

  Discovery of 1,8-disubstituted-[1,2,3]triazolo[4,5-c]quinoline derivatives as a new class of Hippo signaling pathway inhibitors

  摘要：

  Inhibitors of the Hippo signaling pathway have been demonstrated to have a potential clinical application in cases such as tissue repair and organ regeneration. However, there is a lack of potent Hippo pathway inhibitors at present. Herein we report the discovery of a series of 1,8-disubstituted-[1,2,3]triazolo[4,5-c]quinoline derivatives as a new class of Hippo pathway inhibitors by utilizing a cell line-based screening model (A549-CTGF). Structure-activity relationship (SAR) of these compounds was also discussed. The most potent compound in the A549-CTGF cell assay, 11g, was then evaluated by real-time PCR and immunofluorescence assays. Overall, this study provides a starting point for later drug discovery targeting the Hippo signaling pathway.

  DOI：

  10.1016/j.bmcl.2019.08.001
• 作为产物：
  描述：

  2-氨基-5-溴苯甲酸 在 potassium acetate 、 乙酸酐 、 铁粉 、 溶剂黄146 、 三乙胺 、 sodium hydroxide 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 30.0h， 生成 6-bromo-N4-(4-fluorophenyl)quinoline-3,4-diamine
  参考文献：
  名称：

  Discovery of 1,8-disubstituted-[1,2,3]triazolo[4,5-c]quinoline derivatives as a new class of Hippo signaling pathway inhibitors

  摘要：

  Inhibitors of the Hippo signaling pathway have been demonstrated to have a potential clinical application in cases such as tissue repair and organ regeneration. However, there is a lack of potent Hippo pathway inhibitors at present. Herein we report the discovery of a series of 1,8-disubstituted-[1,2,3]triazolo[4,5-c]quinoline derivatives as a new class of Hippo pathway inhibitors by utilizing a cell line-based screening model (A549-CTGF). Structure-activity relationship (SAR) of these compounds was also discussed. The most potent compound in the A549-CTGF cell assay, 11g, was then evaluated by real-time PCR and immunofluorescence assays. Overall, this study provides a starting point for later drug discovery targeting the Hippo signaling pathway.

  DOI：

  10.1016/j.bmcl.2019.08.001

文献信息

• [EN] 1H-IMIDAZO[4,5-C]QUINOLINE DERIVATIVES IN THE TREATMENT OF PROTEIN KINASE DEPENDENT DISEASES<br/>[FR] DERIVES D'1H-IMIDAZO[4,5-C]QUINOLINE DANS LE TRAITEMENT DE MALADIES DEPENDANT DE LA PROTEINE KINASE
  申请人：NOVARTIS AG

  公开号：WO2005054238A1

  公开（公告）日：2005-06-16

  The invention relates to the use of imidazoquinolines and salts thereof in the treatment of protein kinase diseases and for the manufacture of pharmaceutical preparations for the treatment of said diseases, imidazoquinolines for use in the treatment of protein kinase dependent diseases, a method of treatment against said diseases, comprising administering the imidazoquinolines to a warm-blooded animal, especially a human, pharmaceutical preparations comprising an imidazoquinoline, especially for the treatment of a protein kinase dependent disease, novel imidazoquinolines, and a process for the preparation of the novel imidazoquinolines.

  该发明涉及咪唑喹啉及其盐在治疗蛋白激酶疾病以及用于制备治疗该疾病的药物制剂中的应用，咪唑喹啉用于治疗蛋白激酶依赖性疾病，一种治疗上述疾病的方法，包括向温血动物，特别是人类，给予咪唑喹啉，包含咪唑喹啉的药物制剂，特别用于治疗蛋白激酶依赖性疾病，新型咪唑喹啉，以及制备新型咪唑喹啉的方法。
• 1H-Imidazo[4,5-C]Quinoline Derivatives in the Treatment of Protein Kinase Dependent Diseases
  申请人：Capraro Hans-Georg

  公开号：US20070213355A1

  公开（公告）日：2007-09-13

  The invention relates to the use of imidazoquinolines and salts thereof in the treatment of protein kinase dependent diseases and for the manufacture of pharmaceutical preparations for the treatment of said diseases, imidazoquinolines for use in the treatment of protein kinase dependent diseases, a method of treatment against said diseases, comprising administering the imidazoquinolines to a warm-blooded animal, especially a human, pharmaceutical preparations comprising an imidazoquinoline, especially for the treatment of a protein kinase dependent disease, novel imidazoquinolines, and a process for the preparation of the novel imidazoquinolines.

  本发明涉及在蛋白激酶依赖性疾病治疗中使用咪唑喹啉及其盐，并用于制造用于治疗该类疾病的药物制剂，咪唑喹啉用于治疗蛋白激酶依赖性疾病，一种治疗该类疾病的方法，包括向温血动物尤其是人类施用咪唑喹啉，包括咪唑喹啉的药物制剂，特别是用于治疗蛋白激酶依赖性疾病的药物制剂，新型咪唑喹啉以及制备新型咪唑喹啉的方法。
• Discovery of 2-Methyl-2-(4-(2-methyl-8-(1<i>H</i>-pyrrolo[2,3-<i>b</i>]pyridin-6-yl)-1<i>H</i>-naphtho[1,2-<i>d</i>]imidazol-1-yl)phenyl)propanenitrile as a Novel PI3K/mTOR Inhibitor with Enhanced Antitumor Efficacy <i>In Vitro</i> and <i>In Vivo</i>
  作者：Jie Yang、Yuanyuan Liu、Suke Lan、Su Yu、Xinyu Ma、Dan Luo、Huifang Shan、Xinxin Zhong、Guoyi Yan、Rui Li

  DOI：10.1021/acs.jmedchem.2c00572

  日期：2022.10.13

  PI3K/Akt/mTOR signaling pathway is a validated drug target for cancer treatment that plays a critical role in controlling tumor growth, proliferation, and apoptosis. However, no FDA-approved PI3K/mTOR dual inhibitor exists. Thus, a candidate with a better curative effect and lower toxicity is still urgently needed. Herein, we design, synthesize, and evaluate compounds belonging to a novel series of

  PI3K/Akt/mTOR 信号通路是一种经过验证的癌症治疗药物靶点，在控制肿瘤生长、增殖和凋亡方面发挥着关键作用。然而，不存在 FDA 批准的 PI3K/mTOR 双抑制剂。因此，仍迫切需要一种疗效更好、毒性更低的候选药物。在此，我们设计、合成和评估属于新型 2-甲基-1 H-咪唑并[4,5 - c ]喹啉支架衍生物系列的化合物，作为 PI3K/mTOR 双重抑制剂。其中，化合物8o被鉴定为具有优异激酶选择性的新型候选物。它对SW620和HeLa细胞表现出显着的抗增殖活性。Western blot和免疫组化分析结果证明8o可以通过抑制 AKT 和 S6 蛋白的磷酸化来调节 PI3K/AKT/mTOR 信号通路。此外，8o具有良好的药代动力学特性（口服生物利用度为 76.8%）和显着的体内抗肿瘤功效，且无明显毒性。总的来说，这些结果表明8o是一种很有前景的癌症治疗药物，值得进一步开发。
• PI3K/m-TOR抑制剂及其应用
  申请人：四川大学

  公开号：CN117800964A

  公开（公告）日：2024-04-02

  本发明涉及PI3K/m‑TOR抑制剂及其应用，属于靶向抗肿瘤药物技术领域。本发明解决的技术问题是提供一种PI3K/m‑TOR双重选择性抑制剂。本发明化合物，其结构式为式Ⅰ所示。本发明设计并合成了94个全新的以PI3K/m‑TOR为靶点的化合物分子，这些化合物具有优越的抗肿瘤活性和生物安全性，是一种较理想的PI3K/m‑TOR双重选择性抑制剂，在治疗结直肠癌、肺癌或宫颈癌方面有良好的前景。#imgabs0#
• Discovery of 1,8-disubstituted-[1,2,3]triazolo[4,5-c]quinoline derivatives as a new class of Hippo signaling pathway inhibitors
  作者：Jingxin Qiao、Guifeng Lin、Anjie Xia、Zhiyu Xiang、Pei Chen、Guo Zhang、Linli Li、Shengyong Yang

  DOI：10.1016/j.bmcl.2019.08.001

  日期：2019.9

  Inhibitors of the Hippo signaling pathway have been demonstrated to have a potential clinical application in cases such as tissue repair and organ regeneration. However, there is a lack of potent Hippo pathway inhibitors at present. Herein we report the discovery of a series of 1,8-disubstituted-[1,2,3]triazolo[4,5-c]quinoline derivatives as a new class of Hippo pathway inhibitors by utilizing a cell line-based screening model (A549-CTGF). Structure-activity relationship (SAR) of these compounds was also discussed. The most potent compound in the A549-CTGF cell assay, 11g, was then evaluated by real-time PCR and immunofluorescence assays. Overall, this study provides a starting point for later drug discovery targeting the Hippo signaling pathway.