(E)-2-(4-nitrostyryl)quinolin-8-ol | 1204092-95-4

• 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: (E)-2-(4-nitrostyryl)quinolin-8-ol
• 英文别名: 2-[(E)-2-(4-nitrophenyl)vinyl]quinolin-8-ol；(E)-2-[2-(4-nitrophenyl)ethenyl]-8-hydroxyquinoline；2-[(E)-2-(4-nitrophenyl)ethenyl]quinolin-8-ol
• CAS: 1204092-95-4
• 化学式: C₁₇H₁₂N₂O₃
• 分子量: 292.294
• InChiKey: IYNSTUJMKUTNSD-XBXARRHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 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：
  78.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-2-(4-nitrostyryl)quinolin-8-ol 、 zinc diacetate 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以56%的产率得到
  参考文献：
  名称：

  Synthesis, structure, and photoluminescence properties of Zn(II) complexes with 2-styryl derivatives of 8-hydroxyquinoline

  摘要：

  Novel Zn(II) complexes with 2-styryl-8-hydroxyquinoline were synthesized and characterized by H-1, F-19, and C-13 NMR spectroscopy and X-ray diffraction analysis. Photoluminescence properties of the ligands and complexes in solutions were studied. The effect of substituents in the quinoline and phenylethenyl fragments on spectral characteristics was discussed.

  DOI：

  10.1134/s1070363214090229
• 作为产物：
  描述：

  (E)-2-(4-nitrostyryl)quinolin-8-yl acetate 在 盐酸 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以93%的产率得到(E)-2-(4-nitrostyryl)quinolin-8-ol
  参考文献：
  名称：

  New multi-target-directed small molecules against Alzheimer's disease: a combination of resveratrol and clioquinol

  摘要：

  阿尔茨海默病（AD）是目前治疗上最为困难和最具挑战性的疾病之一。结合白藜芦醇和氯碘羟喹的药效团，基于“多靶点导向的配体”（MTDLs）策略，我们设计并合成了一系列新的AD治疗药物。生物活性测试结果表明，这些化合物具有优异的MTDL特性：显著的自发β-淀粉样蛋白（Aβ）聚集抑制能力和铜（II）诱导的Aβ聚集抑制能力，潜在的抗氧化行为（ORAC-FL值为0.9–3.2 Trolox当量）和生物金属螯合作用。在这些化合物中，（E）-5-（4-羟基苯乙烯基）喹啉-8-醇（10c）表现出最强的自发性Aβ聚集抑制能力（IC50 = 8.50 μM）和铜（II）诱导的Aβ聚集抑制能力，以及分解自发和铜（II）诱导的Aβ聚集产生的结构良好的Aβ纤维的能力。需要注意的是，10c还能通过金属配位作用阻止铜的氧化还原循环，从而控制Cu（I/II）触发的羟基自由基（OH·）生成，这一点通过Cu–抗坏血酸盐氧化还原体系检测得到证实。重要的是，在小鼠中，10c在高达2000 mg kg^-1的剂量下未显示急性毒性，并且能够穿过血脑屏障（BBB），这一点通过平行人工膜渗透检测得到证实。这些结果表明，化合物10c是一种有前景的多功能化合物，可用于开发新型AD药物。

  DOI：

  10.1039/c4ob00998c

文献信息

• Photoluminescences and 3D supramolecular structure with unique dimeric Zn (II) units featuring 2-substituted 8-hydroxyquinoline
  作者：Guo-Zan Yuan、Yan-Ping Huo、Lu-Lu Rong、Xiao-Li Nie、Xiao-Ming Fang

  DOI：10.1016/j.inoche.2012.06.015

  日期：2012.9

  A 2-substituted-8-hydroxyquinoline ligand (E)-2-[2-(4-nitrophenyl)ethenyl]-8-hydroxyquinoline (HL) was synthesized and characterized by ESI-MS, NMR spectroscopy and elemental analysis. Using solvothermal method, a dimeric complex [Zn2Cl2L2]center dot 2DMF (1) was fabricated by self-assembly of Zn(II) ions with ligand HL, and characterized with single-crystal X-ray diffractions, powder X-ray diffractions (PXRD), thermal analyses (TGA) and elemental analyses (EA). Complex 1 features a lamellar solid constructed by aromatic stacking interactions and nonclassical C-H center dot center dot center dot O hydrogen bonds. To further investigate the property of the above complex, the photoluminescent properties of 1 are also discussed. (C) 2012 Elsevier B.V. All rights reserved.
• New multi-target-directed small molecules against Alzheimer's disease: a combination of resveratrol and clioquinol
  作者：Fei Mao、Jun Yan、Jianheng Li、Xian Jia、Hui Miao、Yang Sun、Ling Huang、Xingshu Li

  DOI：10.1039/c4ob00998c

  日期：——

  Alzheimer's disease (AD) is currently one of the most difficult and challenging diseases to treat. Based on the ‘multi-target-directed ligands’ (MTDLs) strategy, we designed and synthesised a series of new compounds against AD by combining the pharmacophores of resveratrol and clioquinol. The results of biological activity tests showed that the hybrids exhibited excellent MTDL properties: a significant ability to inhibit self-induced β-amyloid (Aβ) aggregation and copper(II)-induced Aβ aggregation, potential antioxidant behaviour (ORAC-FL value of 0.9–3.2 Trolox equivalents) and biometal chelation. Among these compounds, (E)-5-(4-hydroxystyryl)quinoline-8-ol (10c) showed the most potent ability to inhibit self-induced Aβ aggregation (IC50 = 8.50 μM) and copper(II)-induced Aβ aggregation and to disassemble the well-structured Aβ fibrils generated by self- and copper(II)-induced Aβ aggregation. Note that 10c could also control Cu(I/II)-triggered hydroxyl radical (OH˙) production by halting copper redox cycling via metal complexation, as confirmed by a Cu–ascorbate redox system assay. Importantly, 10c did not show acute toxicity in mice at doses of up to 2000 mg kg−1 and was able to cross the blood–brain barrier (BBB), according to a parallel artificial membrane permeation assay. These results indicate that compound 10c is a promising multifunctional compound for the development of novel drugs for AD.

  阿尔茨海默病（AD）是目前治疗上最为困难和最具挑战性的疾病之一。结合白藜芦醇和氯碘羟喹的药效团，基于“多靶点导向的配体”（MTDLs）策略，我们设计并合成了一系列新的AD治疗药物。生物活性测试结果表明，这些化合物具有优异的MTDL特性：显著的自发β-淀粉样蛋白（Aβ）聚集抑制能力和铜（II）诱导的Aβ聚集抑制能力，潜在的抗氧化行为（ORAC-FL值为0.9–3.2 Trolox当量）和生物金属螯合作用。在这些化合物中，（E）-5-（4-羟基苯乙烯基）喹啉-8-醇（10c）表现出最强的自发性Aβ聚集抑制能力（IC50 = 8.50 μM）和铜（II）诱导的Aβ聚集抑制能力，以及分解自发和铜（II）诱导的Aβ聚集产生的结构良好的Aβ纤维的能力。需要注意的是，10c还能通过金属配位作用阻止铜的氧化还原循环，从而控制Cu（I/II）触发的羟基自由基（OH·）生成，这一点通过Cu–抗坏血酸盐氧化还原体系检测得到证实。重要的是，在小鼠中，10c在高达2000 mg kg^-1的剂量下未显示急性毒性，并且能够穿过血脑屏障（BBB），这一点通过平行人工膜渗透检测得到证实。这些结果表明，化合物10c是一种有前景的多功能化合物，可用于开发新型AD药物。
• Synthesis, structure, and photoluminescence properties of Zn(II) complexes with 2-styryl derivatives of 8-hydroxyquinoline
  作者：E. V. Nosova、G. N. Lipunova、T. V. Stupina、P. A. Slepukhin、M. S. Valova、V. N. Charushin

  DOI：10.1134/s1070363214090229

  日期：2014.9

  Novel Zn(II) complexes with 2-styryl-8-hydroxyquinoline were synthesized and characterized by H-1, F-19, and C-13 NMR spectroscopy and X-ray diffraction analysis. Photoluminescence properties of the ligands and complexes in solutions were studied. The effect of substituents in the quinoline and phenylethenyl fragments on spectral characteristics was discussed.