8-hydroxy-2-methylquinoline-5-carbaldehyde | 5541-73-1

• 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: 8-hydroxy-2-methylquinoline-5-carbaldehyde
• 英文别名: 8-hydroxyquinaldine-5-carbaldehyde；8-hydroxy-2-methyl-quinoline-5-carbaldehyde；8-Hydroxy-2-methyl-chinolin-5-carbaldehyd；5-carbaldehyde-8-hydroxy-2-methylquinoline；2-Methyl-8-hydroxy-chinolin-5-carbaldehyd；2-Methyl-8-hydroxy-chinolin-aldehyd-(5)；8-Hydroxy-2-methylquinoline-5-carbaldehyde
• CAS: 5541-73-1
• 化学式: C₁₁H₉NO₂
• 分子量: 187.198
• InChiKey: VFBGIQGRELQEBD-UHFFFAOYSA-N

物化性质

• 熔点：
  144-144.5 °C(Solv: ethanol (64-17-5))
• 沸点：
  373.1±37.0 °C(Predicted)
• 密度：
  1.307±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-hydroxy-2-methylquinoline-5-carbaldehyde 在 sodium chloride 、 sodium hydroxide 、 magnesium chloride 、 4-羟乙基哌嗪乙磺酸 作用下， 以 水 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of Red-Shifted 8-Hydroxyquinoline Derivatives Using Click Chemistry and Their Incorporation into Phosphorylation Chemosensors

  摘要：

  Protein phosphorylation is a ubiquitous post-translational modification, and protein kinases, the enzymes that catalyze the phosphoryl transfer, are involved in nearly every aspect of normal, as well as aberrant, cell function. Here we describe the synthesis of novel. red-shifted 8-hydroxyquinoline-based fluorophores and their incorporation into peptidyl kinase activity reporters. Replacement of the sulfonamide group of the sulfonamido-oxine (1, Sox) chromophore, which has been previously used In kinase sensing, by a 1,4-substituted triazole moiety prepared via click chemistry resulted in a significant bathochromic shift in the fluorescence excitation (15 nm) and emission (40 rim) maxima for the Mg2+ chelate. Furthermore, when a click derivative was incorporated into a chemosensor for MK2, the kinase accepted the new substrate as efficiently as the previously reported Sox-based sensor. Taken together, these results extend the utility range of kinase sensors that are based on chelation-enhanced fluorescence (CHEF).

  DOI：

  10.1021/jo901369k
• 作为产物：
  描述：

  8-羟基喹哪啶 、 氯仿 在 sodium hydroxide 、 乙醇 、 水 作用下， 生成 8-hydroxy-2-methylquinoline-5-carbaldehyde
  参考文献：
  名称：

  Phillips et al., Transactions of the Kentucky Academy of Science, 1956, vol. 17, p. 135,137

  摘要：

  DOI：

文献信息

• Synthesis, characterization and fluorescent properties of 5-(aryliminomethyl)quinaldine-8-ol derivatives and their trinuclear zinc complexes
  作者：Qing Yan、Longlong Li、Wen Li、Lin Wang、Wen-Hua Sun

  DOI：10.1016/j.saa.2014.03.013

  日期：2014.7

  A series of 5[1-(arylimino)methyl]quinaldine-8-ol derivatives L1-L5 and their trinuclear zinc(II) complexes (C1-C5) were synthesized. The compounds L1-L5 were fully characterized by the FT-IR spectra, NMR measurement and elemental analysis, meanwhile the zinc complexes C1-05 were characterized by the FT-IR spectra and elemental analysis as well as the single crystal X-ray diffraction of a representative complex C3, which revealed a trinuclear zinc complex bearing six organic ligands. The fluorescent properties of both organic compounds and the zinc complexes have been carefully investigated by the UV-Vis absorption in various solvents, indicating the significant influences of the solvents and also double exponential decays. (C) 2014 Elsevier B.V. All rights reserved.
• <i>In Vitro</i>Studies on the Antioxidant and Protective Effect of 2-Substituted -8-Hydroxyquinoline Derivatives Against H₂O₂-Induced Oxidative Stress in BMSCs
  作者：Ting-Ting Wang、Gong-Chang Zeng、Xi-Can Li、He-Ping Zeng

  DOI：10.1111/j.1747-0285.2009.00925.x

  日期：2010.2

  Novel 2‐vinyl‐8‐hydroxyquinoline derivatives as potential antioxidants and regulators of H2O2‐induced oxidative stress in rat bone marrow mesenchymal stem cells (MSCs) are first reported. The antiradical properties and the reducing power of these compounds were assessed using 2, 2‐diphenyl‐1‐picrylhydrazyl (DPPH) and auto‐oxidation of pyrogallol method, respectively. The activity against lipid peroxidation was determined using ammonium thiocyanate method. The results revealed that introduction of electron‐donating groups at 2nd position decreased the antioxidant activities of 8‐hydroxyquinoline derivatives. In addition, compound 4, the structure of which is similar to melatonin, exhibited superior antioxidant activities in scavenging DPPH free radical, ˙O2 free radical, and anti‐LPO activities. Except for compounds 7, 12, and 15, the other compounds exhibited a stimulatory effect on MSCs growth. Using hydrogen peroxide (H2O2), we also investigated the protective efficacy of 2‐vinyl‐8‐hydroxyquinoline derivatives against oxidative stress‐induced cell death of MSCs. Cell viability assayed by MTT method indicated that exposure of MSCs cultures to hydrogen peroxide resulted in a concentration‐dependent decrease in cell viability, and compounds 4 and 5 at given concentration (2.62 × 10−3 m) could protect MSCs against H2O2‐induced oxidative stress in bone mesenchymal stem cell (BMSCs).
• Synthesis of Red-Shifted 8-Hydroxyquinoline Derivatives Using Click Chemistry and Their Incorporation into Phosphorylation Chemosensors
  作者：Juan A. González-Vera、Elvedin Luković、Barbara Imperiali

  DOI：10.1021/jo901369k

  日期：2009.10.2

  Protein phosphorylation is a ubiquitous post-translational modification, and protein kinases, the enzymes that catalyze the phosphoryl transfer, are involved in nearly every aspect of normal, as well as aberrant, cell function. Here we describe the synthesis of novel. red-shifted 8-hydroxyquinoline-based fluorophores and their incorporation into peptidyl kinase activity reporters. Replacement of the sulfonamide group of the sulfonamido-oxine (1, Sox) chromophore, which has been previously used In kinase sensing, by a 1,4-substituted triazole moiety prepared via click chemistry resulted in a significant bathochromic shift in the fluorescence excitation (15 nm) and emission (40 rim) maxima for the Mg2+ chelate. Furthermore, when a click derivative was incorporated into a chemosensor for MK2, the kinase accepted the new substrate as efficiently as the previously reported Sox-based sensor. Taken together, these results extend the utility range of kinase sensors that are based on chelation-enhanced fluorescence (CHEF).
• Phillips et al., Transactions of the Kentucky Academy of Science, 1956, vol. 17, p. 135,137
  作者：Phillips et al.

  DOI：——

  日期：——