6,7-dimethoxy-4-hydroxy-2-methoxycarbonylquinoline | 950277-12-0

• 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: 6,7-dimethoxy-4-hydroxy-2-methoxycarbonylquinoline
• 英文别名: methyl 6,7-dimethoxy-4-oxo-1H-quinoline-2-carboxylate
• CAS: 950277-12-0
• 化学式: C₁₃H₁₃NO₅
• 分子量: 263.25
• InChiKey: XEBZYBSCAVSDHZ-UHFFFAOYSA-N

物化性质

• 沸点：
  414.6±45.0 °C(Predicted)
• 密度：
  1.279±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6,7-dimethoxy-4-hydroxy-2-methoxycarbonylquinoline 在 sodium hydride 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 生成 4-[Cyano-(3,4-dimethoxy-phenyl)-methyl]-6,7-dimethoxy-quinoline-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Quinoline-Carboxylic acids are potent inhibitors that inhibit the binding of insulin-Like growth factor (IGF) to IGF-Binding proteins

  摘要：

  4-Benzylquinolines 5, based on a series of isoquinolines 1, were prepared and tested as inhibitors of the IGF/IGFBP-3 complex based on their ability to displace IGF-I from its binding to IGF-binding protein-3. SAR studies on the 6,7-dihydroxy moiety of the quinoline 5a showed that the catecol moiety could be replaced with other functional groups. Computational modeling of the 5a/mini-IGFBP-5 complex revealed the possible binding site of 5a on IGFBP-5. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00322-6
• 作为产物：
  描述：

  methyl 3-carbomethoxy-3-(3',4'-dimethoxyphenyl)amino-2-propenoate 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 以68%的产率得到6,7-dimethoxy-4-hydroxy-2-methoxycarbonylquinoline
  参考文献：
  名称：

  Neurogenic and neuroprotective donepezil-flavonoid hybrids with sigma-1 affinity and inhibition of key enzymes in Alzheimer's disease

  摘要：

  In this work we describe neurogenic and neuroprotective donepezil-flavonoid hybrids (DFHs), exhibiting nanomolar affinities for the sigma-1 receptor (sigma R-1) and inhibition of key enzymes in Alzheimer's disease (AD), such as acetylcholinesterase (AChE), 5-lipoxygenase (5-LOX), and monoamine oxidases (MAOs). In general, new compounds scavenge free radical species, are predicted to be brain-permeable, and protect neuronal cells against mitochondrial oxidative stress. N-(2-(1-Benzylpiperidin-4-yl)ethyl)-6,7-dimethoxy-4-oxo-4H-chromene-2-carboxamide (18) is highlighted due to its interesting biological profile in sigma R-1, AChE, 5-LOX, MAO-A and MAO-B. In phenotypic assays, it protects a neuronal cell line against mitochondrial oxidative stress and promotes maturation of neural stem cells into a neuronal phenotype, which could contribute to the reparation of neuronal tissues. Molecular modelling studies of 18 in AChE, 5-LOX and sigma R-1 revealed the main interactions with these proteins, which will be further exploited in the optimization of new, more efficient DFHs. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.07.026

文献信息

• Platelet adenosine diphosphate receptor antagonists
  申请人：Schering Aktiengesellschaft

  公开号：US20030060474A1

  公开（公告）日：2003-03-27

  Compounds of the following formula (I): 1 where a, b, R 1 , R 2 , R 4 and R 6 are described herein, are useful as inhibitors of platelet adenosine diphosphate. Pharmaceutical compositions containing these compounds, methods of using these compounds as antithrombotic agents and processes for synthesizing these compounds are also described herein.

  以下公式（I）的化合物：其中a、b、R1、R2、R4和R6如下所述，可用作抑制血小板腺苷二磷酸的药物。本文还描述了含有这些化合物的药物组合物，使用这些化合物作为抗血栓药物的方法以及合成这些化合物的过程。
• New flavonoid – <i>N</i>,<i>N</i>-dibenzyl(<i>N</i>-methyl)amine hybrids: Multi-target-directed agents for Alzheimer´s disease endowed with neurogenic properties
  作者：Martín Estrada-Valencia、Clara Herrera-Arozamena、Concepción Pérez、Dolores Viña、José A. Morales-García、Ana Pérez-Castillo、Eva Ramos、Alejandro Romero、Erik Laurini、Sabrina Pricl、María Isabel Rodríguez-Franco

  DOI：10.1080/14756366.2019.1581184

  日期：2019.1.1

  pathologies. MTDLs that combine neuro-repair properties and block the first steps of neurotoxic cascades could be the so long wanted remedies to treat neurodegenerative diseases (NDs). By linking two privileged scaffolds with well-known activities in ND-targets, the flavonoid and the N,N-dibenzyl(N-methyl)amine (DBMA) fragments, new CNS-permeable flavonoid - DBMA hybrids (1-13) were obtained. They were

  多靶标定向配体（MTDLs）的设计是获得有效的复杂病理学药物的有效方法。结合神经修复特性并阻断神经毒性级联反应第一步的MTDL可能是治疗神经退行性疾病（ND）的长期以来一直希望的补救措施。通过将两个具有众所周知的ND目标活性的特权支架，类黄酮和N，N-二苄基（N-甲基）胺（DBMA）片段连接起来，获得了新的CNS渗透性类黄酮-DBMA杂种（1-13）。 。他们在一系列涉及阿尔茨海默氏病（AD）和其他ND的靶标中进行了生物学评估，这些靶标分别是人胆碱酯酶（hAChE / hBuChE），β-分泌酶（hBACE-1），单胺氧化酶（hMAO-A / B），脂氧合酶5（hLOX-5）和sigMA受体（σ1R/σ2R）。经过漏斗式筛选后，6 7-二甲氧基色酮-DBMA（6）因其具有神经源性和在hAChE，hLOX-5，hBACE-1和σ1R中具有有趣的MTD谱而突出显示。分子动力学模拟显示杂种6最相
• PIPERAZINE OXYQUINOLINE (NAPHTHALINE) PLATELET ADENOSINE DIPHOSPHATE RECEPTOR ANTAGONISTS
  申请人：Schering Aktiengesellschaft

  公开号：EP1412349A2

  公开（公告）日：2004-04-28
• 2-AMINOCARBONYL-QUINOLINE COMPOUNDS AS PLATELET ADENOSINE DIPHOSPHATE RECEPTOR ANTAGONISTS
  申请人：Bayer Schering Pharma Aktiengesellschaft

  公开号：EP1578423B1

  公开（公告）日：2010-08-18
• US6861424B2
  申请人：——

  公开号：US6861424B2

  公开（公告）日：2005-03-01