4-methoxy-2-(4-hydroxyphenyl)quinoline | 1155883-51-4

• 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-2-(4-hydroxyphenyl)quinoline
• 英文别名: 4-(4-Methoxyquinolin-2-yl)phenol；4-(4-methoxyquinolin-2-yl)phenol
• CAS: 1155883-51-4
• 化学式: C₁₆H₁₃NO₂
• 分子量: 251.285
• InChiKey: JGLRWLSSISVYMY-UHFFFAOYSA-N

物化性质

• 沸点：
  403.7±35.0 °C(predicted)
• 密度：
  1.228±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  42.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-(4-methoxyquinolin-2-yl)phenyl acetate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 以78%的产率得到4-methoxy-2-(4-hydroxyphenyl)quinoline
  参考文献：
  名称：

  路易斯酸促进炔烃的氧离子驱动的碳氨化反应，以合成4-烷氧基喹啉

  摘要：

  路易斯酸介导的多段偶联级联反应是设计用于通过含氧离子触发的炔烃碳氨化序列（涉及C–C和C–N键的形成）来合成密集取代的4-烷氧基喹啉。还可以使用这种快速，操作简单，高收率，化学选择性和功能基团耐受的方法获得环醚稠合喹啉。该方法的多功能性和实用性通过所获得产品的后功能化及其在有效药物分子合成中的应用来证明。

  DOI：

  10.1021/acs.joc.6b02896

文献信息

• [EN] POLYPHENOL ANALOGS TO TREAT ISCHEMIA<br/>[FR] ANALOGUES DE POLYPHÉNOL POUR TRAITER UNE ISCHÉMIE
  申请人：LAPCHAK PAUL A

  公开号：WO2013025484A1

  公开（公告）日：2013-02-21

  The present invention provides methods of use of polyphenol compounds for treating, preventing, mitigating and delaying ischemia or a condition where ischemia occurs. In one embodiment, the method comprises providing a polyphenol analog; and administering the polyphenol analog to a subject to treat ischemia or a condition where ischemia occurs. Various embodiments of the present invention are useful for the treatment of patients having, or at risk for, any of (1) ischemic stroke, (2) hemorrhagic stroke, (3) cardiovascular disease, (4) ischemia related spinal cord injury, (5) ischemia in diabetic patients, or (6) embolic stroke.. For example, use of the polyphenol compounds can maintain glutathione levels in the patient.

  本发明提供了使用多酚化合物治疗、预防、缓解和延迟缺血或发生缺血状况的方法。在一个实施方式中，该方法包括提供一种多酚类似物；并将该多酚类似物给予受试者以治疗缺血或发生缺血状况。本发明的各种实施方式适用于治疗患有或有风险患有以下任何一种疾病的患者：（1）缺血性中风，（2）出血性中风，（3）心血管疾病，（4）与缺血有关的脊髓损伤，（5）糖尿病患者的缺血，或（6）栓塞性中风。例如，使用多酚化合物可以维持患者的谷胱甘肽水平。
• [EN] NEUROPROTECTIVE POLYPHENOL ANALOGS<br/>[FR] ANALOGUES DU POLYPHÉNOL NEUROPROTECTEURS
  申请人：SCHUBERT DAVID R

  公开号：WO2013025498A1

  公开（公告）日：2013-02-21

  The present invention provides neuroprotective polyphenol compounds, which can be synthetic analogs of fisetin, baicalein or chlorogenic acid, that maintain neuroprotective, anti-inflammatory, glutathione promoting, and/or antioxidant properties. The neuroprotective polyphenol compounds are useful for promoting, enhancing and/or increasing neuron protection, growth and/or regeneration. The polyphenol compounds further find use for increasing and or maintaining intracellular glutathione (GSH) levels. The polyphenol compounds are also useful for treating, preventing, mitigating and/or delaying neurodegenerative conditions, including diabetes, Parkinson's disease, Huntington's disease, Alzheimer's disease, non-Alzherimer's dementias, multiple sclerosis, traumatic brain injury, spinal cord injury or ALS.

  本发明提供了神经保护多酚化合物，可以是嘌呤、黄芩素或绿原酸的合成类似物，这些化合物具有保持神经保护、抗炎、促进谷胱甘肽以及抗氧化性能。这些神经保护多酚化合物可用于促进、增强和/或增加神经元的保护、生长和/或再生。多酚化合物还可用于增加和/或维持细胞内谷胱甘肽（GSH）水平。多酚化合物还可用于治疗、预防、缓解和/或延缓神经退行性疾病，包括糖尿病、帕金森病、亨廷顿病、阿尔茨海默病、非阿尔茨海默病性痴呆、多发性硬化症、创伤性脑损伤、脊髓损伤或肌萎缩侧索硬化症（ALS）。
• Sulfuric acid promoted condensation cyclization of 2-(2-(trimethylsilyl) ethynyl)anilines with arylaldehydes in alcoholic solvents: an efficient one-pot synthesis of 4-alkoxy-2-arylquinolines
  作者：Yong Wang、Changlan Peng、Lanying Liu、Jiaji Zhao、Li Su、Qiang Zhu

  DOI：10.1016/j.tetlet.2009.02.206

  日期：2009.5

  An efficient method for the synthesis of 4-alkoxy-2-arylquinolines has been developed. The reaction proceeds smoothly by heating a mixture of easily accessible 2-(2-(trimethylsilyl) ethynyl)anilines and arylaldehydes in alcoholic solvents in the presence of sulfuric acid. (C) 2009 Elsevier Ltd. All rights reserved.
• Chemical Modification of the Multitarget Neuroprotective Compound Fisetin
  作者：Chandramouli Chiruta、David Schubert、Richard Dargusch、Pamela Maher

  DOI：10.1021/jm2012563

  日期：2012.1.12

  Many factors are implicated in age-related central nervous system (CNS) disorders, making it unlikely that modulating only a single factor will provide effective treatment. Perhaps a better approach is to identify small molecules that have multiple biological activities relevant to the maintenance of brain function. Recently, we identified an orally active, neuroprotective, and cognition-enhancing molecule, the flavonoid fisetin, that is effective in several animal models of CNS disorders. Fisetin has direct antioxidant activity and can also increase the intracellular levels of glutathione (GSH), the major endogenous antioxidant. In addition, fisetin has both neurotrophic and anti-inflammatory activity. However, its relatively high EC50 in cell based assays, low lipophilicity, high topological polar surface area (tPSA), and poor bioavailability suggest that there is room for medicinal chemical improvement. Here we describe a multitiered approach to screening that has allowed us to identify fisetin derivatives with significantly enhanced activity in an in vitro neuroprotection model while at the same time maintaining other key activities.
• NEUROPROTECTIVE POLYPHENOL ANALOGS
  申请人：Salk Institute for Biological Studies

  公开号：EP2741609A1

  公开（公告）日：2014-06-18