2-[(8-hydroxyquinolinyl)methylene]hydrazinecarboxamide | 536718-27-1

• 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: 2-[(8-hydroxyquinolinyl)methylene]hydrazinecarboxamide
• 英文别名: [(8-hydroxyquinolin-2-yl)methylideneamino]urea
• CAS: 536718-27-1
• 化学式: C₁₁H₁₀N₄O₂
• 分子量: 230.226
• InChiKey: BEDKTPFEKJJFEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  101
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  copper(II) acetate monohydrate 、 2-[(8-hydroxyquinolinyl)methylene]hydrazinecarboxamide 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以99%的产率得到bis(2-[(8-hydroxyquinolinyl)methylene]hydrazinecarboxamide-H)copper(II)
  参考文献：
  名称：

  8-Hydroxyquinoline Schiff-base compounds as antioxidants and modulators of copper-mediated Aβ peptide aggregation

  摘要：

  One of the hallmarks of Alzheimer's disease (AD) in the brain are amyloid-β (Aβ) plaques, and metal ions such as copper(II) and zinc(II) have been shown to play a role in the aggregation and toxicity of the Aβ peptide, the major constituent of these extracellular aggregates. Metal binding agents can promote the disaggregation of Aβ plaques, and have shown promise as AD therapeutics. Herein, we describe the syntheses and characterization of an acetohydrazone (8-H2QH), a thiosemicarbazone (8-H2QT), and a semicarbazone (8-H2QS) derived from 8-hydroxyquinoline. The three compounds are shown to be neutral at pH7.4, and are potent antioxidants as measured by a Trolox Equivalent Antioxidant Capacity (TEAC) assay. The ligands form complexes with Cu(II), 8-H2QT in a 1:1 metal:ligand ratio, and 8-H2QH and 8-H2QS in a 1:2 metal:ligand ratio. A preliminary aggregation inhibition assay using the Aβ1-40 peptide showed that 8-H2QS and 8-H2QH inhibit peptide aggregation in the presence of Cu(II). Native gel electrophoresis/Western blot and TEM images were obtained to give a more detailed picture of the extent and pathways of Aβ aggregation using the more neurotoxic Aβ1-42 in the presence and absence of Cu(II), 8-H2QH, 8-H2QS and the drug candidate PBT2. An increase in the formation of oligomeric species is evident in the presence of Cu(II). However, in the presence of ligands and Cu(II), the results match those for the peptide alone, suggesting that the ligands function by sequestering Cu(II) and limiting oligomer formation in this assay.

  DOI：

  10.1016/j.jinorgbio.2014.04.011
• 作为产物：
  描述：

  8-羟基喹啉-2-甲醛 、 盐酸氨基脲 在 sodium acetate 作用下， 以 水 、 乙醇 为溶剂， 反应 4.0h， 以95%的产率得到2-[(8-hydroxyquinolinyl)methylene]hydrazinecarboxamide
  参考文献：
  名称：

  8-Hydroxyquinoline Schiff-base compounds as antioxidants and modulators of copper-mediated Aβ peptide aggregation

  摘要：

  One of the hallmarks of Alzheimer's disease (AD) in the brain are amyloid-β (Aβ) plaques, and metal ions such as copper(II) and zinc(II) have been shown to play a role in the aggregation and toxicity of the Aβ peptide, the major constituent of these extracellular aggregates. Metal binding agents can promote the disaggregation of Aβ plaques, and have shown promise as AD therapeutics. Herein, we describe the syntheses and characterization of an acetohydrazone (8-H2QH), a thiosemicarbazone (8-H2QT), and a semicarbazone (8-H2QS) derived from 8-hydroxyquinoline. The three compounds are shown to be neutral at pH7.4, and are potent antioxidants as measured by a Trolox Equivalent Antioxidant Capacity (TEAC) assay. The ligands form complexes with Cu(II), 8-H2QT in a 1:1 metal:ligand ratio, and 8-H2QH and 8-H2QS in a 1:2 metal:ligand ratio. A preliminary aggregation inhibition assay using the Aβ1-40 peptide showed that 8-H2QS and 8-H2QH inhibit peptide aggregation in the presence of Cu(II). Native gel electrophoresis/Western blot and TEM images were obtained to give a more detailed picture of the extent and pathways of Aβ aggregation using the more neurotoxic Aβ1-42 in the presence and absence of Cu(II), 8-H2QH, 8-H2QS and the drug candidate PBT2. An increase in the formation of oligomeric species is evident in the presence of Cu(II). However, in the presence of ligands and Cu(II), the results match those for the peptide alone, suggesting that the ligands function by sequestering Cu(II) and limiting oligomer formation in this assay.

  DOI：

  10.1016/j.jinorgbio.2014.04.011

文献信息

• 2-[(8-Hydroxyquinolinyl)methylene]hydrazinecarboxamide: expanding the coordination sphere of 8-hydroxyquinoline for coordination of rare-earth metal(iii) ions
  作者：Markus Albrecht、Olga Osetska、Roland Fröhlich

  DOI：10.1039/b507621h

  日期：——

  The semicarbazone of 8-hydroxyquinoline-2-carbaldehyde can be easily synthesized and is an effective tetradentate ligand for the coordination of rare-earth(III) ions. Investigations with yttrium(III) and lanthanum(III) in solution and in the solid state show, that the small yttrium ion can form 2 : 2 (1 : 1 stoichiometry) and 2 : 1 ligand to metal complexes (X-ray structures: [LY(NO3)(DMF)2]2Cl2·2DMF and [LL′Y]·3MeOH·Et2O). With the larger lanthanum(III) ion only a well defined 1 : 1 complex (X-ray structure: [LLa(NO3)(MeOH)2]2(NO3)2) can be observed but probably 2 : 1 complexes are also formed. The X-ray structure analyses of [(L-H)MCl3]·MeOH (M = Er, Ho) and Na[(μ-NO3)LEu(NO3)2}2]·2DMF show different coordination modes of the ligand. It can coordinate in its deprotonated but also in the protonated form.

  8- 羟基喹啉-2-甲醛的半咔唑酮很容易合成，是配位稀土（III）离子的有效四价配体。对溶液和固态钇（III）和镧（III）的研究表明，小钇离子可以与金属配合物形成 2 : 2（1 : 1 配比）和 2 : 1 配体（X 射线结构：[LY(NO3)( )( )]）：[LY( )(DMF)2]2Cl2-2DMF 和 [LL′Y]-3MeOH-Et2O）。对于较大的镧(III)离子，只有一个明确的 1 : 1 复合物（X 射线结构：[LLa( )(DMF)2]2Cl2-2DMF 和 [LL′Y]-3MeOH-Et2O可以观察到[LLa( )(MeOH)2]2( )2），但也可能形成 2:1 的络合物。对[(L-H)MCl3]-MeOH（M = Er、Ho）和 Na[(μ- )LEu( )2}2]-2DMF 的 X 射线结构分析表明，配体具有不同的配位模式。它可以以去质子化形式配位，也可以以质子化形式配位。