2-[2-(4-nitrophenyl)ethenyl]quinolin-8-ol | 442555-76-2

• 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-[2-(4-nitrophenyl)ethenyl]quinolin-8-ol
• 英文别名: 2-[2-(4-nitrophenyl)vinyl]quinolin-8-ol
• CAS: 442555-76-2
• 化学式: C₁₇H₁₂N₂O₃
• mdl: MFCD04952162
• 分子量: 292.294
• InChiKey: IYNSTUJMKUTNSD-UHFFFAOYSA-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：

  2-[2-(4-nitrophenyl)ethenyl]quinolin-8-ol 、 丹酰氯 在 三乙胺 作用下， 以 氯仿 为溶剂， 生成 DansSQ
  参考文献：
  名称：

  Dansyl-styrylquinoline conjugate as divalent iron sensor

  摘要：

  Synthesis and photophysical studies of a simple and efficient dansyl-styrylquinoline conjugate (DansSQ) which shows excellent selectivity towards Fe2+ over other transition metal ions including Fe3+ is described. The fluorescent emission of DansSQ at 450 nm was enhanced upon addition of Fe2+ in the presence of common interfering metal ions in background. The studies suggest that DansSQ could be used as fluorescent sensor for Fe2+. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.10.043
• 作为产物：
  描述：

  对硝基苯甲醛 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 生成 2-[2-(4-nitrophenyl)ethenyl]quinolin-8-ol
  参考文献：
  名称：

  Design, synthesis, and photochemistry of styrylquinoline -containing polymers

  摘要：

  Novel polymers with styrylquinoline moiety and different substituents units are presented. Styrylquinoline polymers were obtained by a three-step synthetic approach. This includes the condensation, preparation of a methacrylic monomers and their polymerization. Their photophysical and photochemical properties have been investigated. Polymers were characterized by (HNMR)-H-1, UV spectroscopy and GPC, DSC techniques. The synthesized polymers exhibited glass transition temperatures in the range of 153-184 degrees C.

  DOI：

  10.1080/15421406.2016.1255516

文献信息

• Synthesis of six 8-quinolinate-based ruthenium complexes with high catalytic activity for nitroarene reduction
  作者：Wei-Guo Jia、Ming-Xia Cheng、Qiu-Tong Xu、Li-Li Gao、Guozan Yuan

  DOI：10.1016/j.poly.2018.06.054

  日期：2018.10

  interactions, such as π⋯π stacking, hydrogen-bonding and C H⋯ halogen interactions. The catalytic activities of the six half-sandwich ruthenium complexes towards the hydrogenation of nitroarenes were explored under mild conditions. The ruthenium complexes displayed high catalytic activities in the synthesis of aromatic anilines from nitroarenes in the presence of NaBH4.

  摘要用[Ru（对异丙基）（μ-Cl）Cl] 2处理不同的2-取代的8-羟基喹啉酸酯配体，合成了六种钌配合物。它们的结构已通过多种技术进行了充分表征，包括1H和13C NMR光谱，元素分析和红外光谱。此外，单晶X射线衍射显示这些钌配合物具有相似的半三明治结构。单核钌构建单元通过非共价相互作用（例如π⋯π堆积，氢键和CH 3卤素相互作用）进一步连接到1D或2D超分子结构中。在温和条件下研究了六种半三明治钌络合物对硝基芳烃氢化的催化活性。
• Synthesis and antiproliferative evaluations of certain 2-phenylvinylquinoline (2-styrylquinoline) and 2-furanylvinylquinoline derivatives
  作者：Feng-Shuo Chang、Weichung Chen、Chihuei Wang、Cherng-Chyi Tzeng、Yeh-Long Chen

  DOI：10.1016/j.bmc.2009.11.012

  日期：2010.1

  describes the synthesis of 2-phenylvinylquinoline (styrylquinoline) and 2-furanylvinylquinoline derivatives and evaluation for their antiproliferative activities. (E)-2-Styrylquinolin-8-ol (14a) was inactive against a 3-cell line panel consisting of MCF-7 (Breast), NCI-H460 (Lung), and SF-268 (CNS). Replacement of the phenyl ring with 5-nitrofuran-2-yl group significantly enhanced antiproliferative activity

  本研究描述了2-苯基乙烯基喹啉（苯乙烯基喹啉）和2-呋喃基乙烯基喹啉衍生物的合成及其抗增殖活性的评价。（E）-2-苯乙烯基喹啉-8-ol（14a）对由MCF-7（乳腺癌），NCI-H460（肺）和SF-268（CNS）组成的3细胞系细胞系无活性。用（5-硝基呋喃-2-基）取代苯环可显着增强抗增殖活性，其中（E）-2-（2-（5-（硝基呋喃-2-基）乙烯基）喹啉-8-醇（14i）及其4-取代的衍生物15 - 19起所有三种癌症细胞的生长表现出强烈的抑制作用。进一步评估了这些化合物的IC 50反对MCF-7，LNCaP和PC3的增长。结果表明，提供氢键的肟衍生物19a比接受甲基肟的衍生物氢19b更具活性。对于LNCaP的抑制，效力以14i  >  19a  >  19b  >  15  >  18  >  16的顺序降低。化合物14i对LNCaP和PC3癌细胞的生长最为活跃，其IC 50值分别为0
• UV irradiation induce NLO modulation in photochromic styrylquinoline-based polymers: Computational and experimental studies
  作者：Dominique Guichaoua、Bohdan Kulyk、Vitaliy Smokal、Anna Migalska-Zalas、Oksana Kharchenko、Oksana Krupka、Oleksiy Kolendo、Bouchta Sahraoui

  DOI：10.1016/j.orgel.2018.12.022

  日期：2019.3

  containing methacrylic polymers studied by using Maker fringes technique employing 30 ps laser pulses at fundamental wavelength of 1064 nm are presented. Photochromic styrylquinoline units were oriented in the thin films by corona poling technique promoting second order NLO activity. Strong dependence of the NLO response upon the structure of the polymers has been found, which is related to the different charge

  在过去的几十年中，功能化的光致变色材料吸引了越来越多的兴趣，因为它们是有望用于光电子学和光子学的材料。本文通过使用Maker条纹技术，在基本波长为1064的条件下使用30 ps激光脉冲研究了旋涂沉积的含甲基丙烯酸苯乙烯基喹啉的高质量薄膜的非线性光学（NLO）研究的结果（二次谐波和三次谐波的产生）提出了nm。通过电晕极化技术促进薄膜的二阶NLO活性，使光致变色的苯乙烯基喹啉单元在薄膜中取向。已经发现NLO响应对聚合物结构的强烈依赖性，这与苯乙烯基喹啉片段内的不同电荷转移有关。这些研究是通过使用HOMO-LUMO能级理论以及一阶和二阶超极化率值进行的理论研究完成的。理论和实验结果之间已经取得了良好的兼容性。研究过的基于苯乙烯基喹啉的聚合物在NLO反应后表现出对比反式顺式光异构化使它们在光子器件中的使用变得有趣。
• Antitumor activity of iridium/ruthenium complexes containing Nitro -substituted quinoline ligands in vivo and in vitro
  作者：Xiangdong He、Jun Chen、Lai Wei、Martha Kandawa-Shultz、Guoqiang Shao、Yihong Wang

  DOI：10.1016/j.dyepig.2023.111146

  日期：2023.5

  Four iridium/ruthenium half-sandwich metal complexes containing 8-hydroxyquinoline ligands were synthesized as anticancer agents. In vitro toxicity results showed that all complexes had outstanding antitumor activity against a variety of tumor cells, especially the MDA-MB-231 cell. The complex could initiate downstream apoptotic signals through the lysosomal damage pathway and the reactive oxygen species

  合成了四种含有 8-羟基喹啉配体的铱/钌半夹心金属配合物作为抗癌剂。体外毒性结果表明，所有配合物均对多种肿瘤细胞，尤其是MDA-MB-231细胞具有突出的抗肿瘤活性。该复合物可通过溶酶体损伤途径启动下游细胞凋亡信号，同时产生的活性氧（ROS）可进一步加重溶酶体损伤。此外，该复合物在体内显着抑制乳腺癌小鼠异种移植模型中的肿瘤生长。
• Supramolecular assembly of two two-folded helical structures based on 2-substituted 8-hydroxyquinoline complexes
  作者：Guozan Yuan、Lulu Rong、Caibo Yue、Xianwen Wei

  DOI：10.1016/j.inoche.2013.03.036

  日期：2013.7

  Based on two 2-substituted 8-hydroxyquinoline ligands containing -NO2 and -Cl, two complexes [Co(L-2)(2)(pyridine)(2)] (1) and [Cu(L-3)(2)] (2) were synthesized and characterized with single-crystal X-ray diffractions, powder X-ray diffractions (PXRD), thermal analyses (TGA) and elemental analyses (EA). In the solid state, the supramolecular structures of 1 and 2 feature two different two-folded helical chains, which were constructed by non-covalent interactions, such as pi-pi stacking, C-H...pi and C-H center dot center dot center dot O, C-Cl...pi and Cl center dot center dot center dot Cl interactions. The present research holds great promise in the development of novel functional helical structure, and may contribute to the understanding of helical organized systems in biology. (c) 2013 Elsevier B.V. All rights reserved.