5,7-dichloro-2-[2-(2-chlorophenyl)vinyl]quinolin-8-ol | 796860-41-8

• 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: 5,7-dichloro-2-[2-(2-chlorophenyl)vinyl]quinolin-8-ol
• 英文别名: 5,7-Dichloro-2-[2-(2-chlorophenyl)ethenyl]quinolin-8-ol
• CAS: 796860-41-8
• 化学式: C₁₇H₁₀Cl₃NO
• 分子量: 350.632
• InChiKey: PTQSJEUQNINTFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 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：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-[ReOCl3(PPh3)2] 、 5,7-dichloro-2-[2-(2-chlorophenyl)vinyl]quinolin-8-ol 以 乙腈 为溶剂， 反应 6.0h， 以70%的产率得到
  参考文献：
  名称：

  8-羟基喹啉衍生物的新型氧化or（V）配合物–合成，光谱表征，X射线晶体结构和DFT计算

  摘要：

  8-羟基喹啉骨架的两个修饰，即5,7-二氯-2- [2-（2-（2-氯苯基）乙烯基]喹啉-8-ol（HL 1）和2- [2-（3,4-二氯苯基）乙烯基合成了] quinoline-8-ol（HL 2），并研究了它们与[ReOX 3（PPh 3）2 ]（X = Cl，Br）的相互作用。HL 1和HL 2与[ReOX 3（PPh 3）2 ]反应，得到[ReOCl 2（L 1）（PPh 3）] 2 ·MeCN（1），[ReOBr 2（L 1）（PPh 3）]（2），[ReOCl 2（L 2）（PPh 3）]（3）和[ReOBr 2（L 2）（PPh 3）]（4）。配合物已在光谱和结构上进行了表征。DFT计算伴随着对1和3的实验研究，并且通过NBO分析获得了有关atom原子与氧代配体之间结合的更多信息。X射线研究和NBO分析证实了and与末端氧代配体之间的三键。L 1和L 2配体通过N-和O-供体

  DOI：

  10.1016/j.poly.2012.12.028
• 作为产物：
  描述：

  5,7-dichloro-2-[2-(2-chlorophenyl)vinyl]quinolin-8-yl acetate 在 吡啶 、 水 作用下， 反应 3.0h， 生成 5,7-dichloro-2-[2-(2-chlorophenyl)vinyl]quinolin-8-ol
  参考文献：
  名称：

  Design, Synthesis and In Vitro Activity of Anticancer Styrylquinolines. The p53 Independent Mechanism of Action

  摘要：

  一组苯乙烯基喹啉被合成并测试其抗增殖活性。抗增殖活性对人类结肠癌细胞系进行评估，这些细胞系正常表达p53蛋白（HCT116 p53+/+）以及带有失活TP53基因的突变体（HCT116 p53-/-），同时还对GM 07492正常人类成纤维细胞系进行评估。一项SAR研究揭示了氯和羟基作为苯乙烯部分取代基的重要性。测试中的几个化合物被发现具有显著的抗增殖活性，其活性与或优于多柔比星，并且在p53缺失细胞中活性更强于野生型细胞。细胞定位测试和半胱天冬酶活性测定表明其作用机制通过线粒体途径以非p53依赖的方式诱导细胞凋亡。苯乙烯基喹啉化合物的活性可能与其DNA插层能力有关。

  DOI：

  10.1371/journal.pone.0142678

文献信息

• The synthesis and anticancer activity of 2-styrylquinoline derivatives. A p53 independent mechanism of action
  作者：Anna Mrozek-Wilczkiewicz、Michał Kuczak、Katarzyna Malarz、Wioleta Cieślik、Ewelina Spaczyńska、Robert Musiol

  DOI：10.1016/j.ejmech.2019.05.061

  日期：2019.9

  A series of styrylquinolines was designed and synthesized based on the four main quinoline scaffolds including oxine, chloroxine and quinolines substituted with a hydroxyl group or chlorine atom at the C4 position. All of the compounds were tested for their anticancer activity on wild-type colon cancer cells (HCT 116) and those with a p53 deletion. Analysis of SAR revealed the importance of electron-withdrawing

  基于四个主要的喹啉骨架设计并合成了一系列的苯乙烯基喹啉，这些骨架包括在C4位置被羟基或氯原子取代的牛，氯辛和喹啉。测试了所有化合物对野生型结肠癌细胞（HCT 116）和具有p53缺失的癌细胞的抗癌活性。SAR分析表明，在苯乙烯基部分有吸电子取代基，在喹啉环上具有螯合性能。还在TP53突变的4种癌细胞系中测试了活性更高的化合物肿瘤抑制基因。结果表明，苯乙烯基喹啉可诱导细胞周期停滞并激活p53非依赖性细胞凋亡。研究了最有前途的化合物的表观作用机理，这些化合物产生了活性氧，并改变了细胞的氧化还原平衡。
• Contribution to investigation of antimicrobial activity of styrylquinolines
  作者：Wioleta Cieslik、Robert Musiol、Jacek E. Nycz、Josef Jampilek、Marcela Vejsova、Mariusz Wolff、Barbara Machura、Jaroslaw Polanski

  DOI：10.1016/j.bmc.2012.10.027

  日期：2012.12

  Series of new ring-substituted styrylquinolines and two oxorhenium complexes were prepared and characterized. The compounds were analyzed using RP-HPLC to determine lipophilicity. Primary in vitro screening of the synthesized compounds was performed against fungal and bacterial strains. Some compounds were active against bacteria at micromolar level and against fungi at submicromolar level. Compounds 5,7-dichloro-2-[2-(2-ethoxyphenyl)vinyl]quinolin-8-ol expressed excellent antifungal activity comparable with or higher than the standard fluconazole as well as antibacterial activity against Staphylococcus strains comparable with or higher than the standards bacitracin, penicillin and ciprofloxacin. The structure-activity relationships are discussed. (C) 2012 Elsevier Ltd. All rights reserved.
• Design, Synthesis and In Vitro Activity of Anticancer Styrylquinolines. The p53 Independent Mechanism of Action
  作者：Anna Mrozek-Wilczkiewicz、Ewelina Spaczynska、Katarzyna Malarz、Wioleta Cieslik、Marzena Rams-Baron、Vladimír Kryštof、Robert Musiol

  DOI：10.1371/journal.pone.0142678

  日期：——

  A group of styrylquinolines were synthesized and tested for their anti-proliferative activity. Anti-proliferative activity was evaluated against the human colon carcinoma cell lines that had a normal expression of the p53 protein (HCT116 p53+/+) and mutants with a disabled TP53 gene (HCT116 p53-/-) and against the GM 07492 normal human fibroblast cell line. A SAR study revealed the importance of Cl and OH as substituents in the styryl moiety. Several of the compounds that were tested were found to have a marked anti-proliferative activity that was similar to or better than doxorubicin and were more active against the p53 null than the wild type cells. The cellular localization tests and caspase activity assays suggest a mechanism of action through the mitochondrial pathway of apoptosis in a p53-independent manner. The activity of the styrylquinoline compounds may be associated with their DNA intercalating ability.

  一组苯乙烯基喹啉被合成并测试其抗增殖活性。抗增殖活性对人类结肠癌细胞系进行评估，这些细胞系正常表达p53蛋白（HCT116 p53+/+）以及带有失活TP53基因的突变体（HCT116 p53-/-），同时还对GM 07492正常人类成纤维细胞系进行评估。一项SAR研究揭示了氯和羟基作为苯乙烯部分取代基的重要性。测试中的几个化合物被发现具有显著的抗增殖活性，其活性与或优于多柔比星，并且在p53缺失细胞中活性更强于野生型细胞。细胞定位测试和半胱天冬酶活性测定表明其作用机制通过线粒体途径以非p53依赖的方式诱导细胞凋亡。苯乙烯基喹啉化合物的活性可能与其DNA插层能力有关。
• Novel oxorhenium(V) complexes of 8-hydroxyquinoline derivatives – Synthesis, spectroscopic characterization, X-ray crystal structures and DFT calculations
  作者：B. Machura、M. Wolff、W. Cieślik、R. Musioł

  DOI：10.1016/j.poly.2012.12.028

  日期：2013.3

  [ReOBr2(L1)(PPh3)] (2), [ReOCl2(L2)(PPh3)] (3) and [ReOBr2(L2)(PPh3)] (4). The complexes have been characterized spectroscopically and structurally. The experimental studies on 1 and 3 have been accompanied by DFT calculations, and additional information about binding between the rhenium atom and oxo ligand has been obtained by NBO analysis. The X-ray studies and NBO analysis confirm a triple bond between the rhenium

  8-羟基喹啉骨架的两个修饰，即5,7-二氯-2- [2-（2-（2-氯苯基）乙烯基]喹啉-8-ol（HL 1）和2- [2-（3,4-二氯苯基）乙烯基合成了] quinoline-8-ol（HL 2），并研究了它们与[ReOX 3（PPh 3）2 ]（X = Cl，Br）的相互作用。HL 1和HL 2与[ReOX 3（PPh 3）2 ]反应，得到[ReOCl 2（L 1）（PPh 3）] 2 ·MeCN（1），[ReOBr 2（L 1）（PPh 3）]（2），[ReOCl 2（L 2）（PPh 3）]（3）和[ReOBr 2（L 2）（PPh 3）]（4）。配合物已在光谱和结构上进行了表征。DFT计算伴随着对1和3的实验研究，并且通过NBO分析获得了有关atom原子与氧代配体之间结合的更多信息。X射线研究和NBO分析证实了and与末端氧代配体之间的三键。L 1和L 2配体通过N-和O-供体