2-[2-(2,6-dichlorophenyl)vinyl]quinolin-8-ol | 426243-89-2

• 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-(2,6-dichlorophenyl)vinyl]quinolin-8-ol
• 英文别名: 2-[2-(2,6-Dichlorophenyl)ethenyl]quinolin-8-ol
• CAS: 426243-89-2
• 化学式: C₁₇H₁₁Cl₂NO
• mdl: MFCD01836953
• 分子量: 316.186
• InChiKey: XXDAPKIGZDFBEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  21
• 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：

  copper(II) nitrate trihydrate 、 2-[2-(2,6-dichlorophenyl)vinyl]quinolin-8-ol 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以75%的产率得到
  参考文献：
  名称：

  Supramolecular assembly of two two-folded helical structures based on 2-substituted 8-hydroxyquinoline complexes

  摘要：

  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.

  DOI：

  10.1016/j.inoche.2013.03.036
• 作为产物：
  描述：

  2-[2-(2,6-dichlorophenyl)vinyl]quinolin-8-yl acetate 在 吡啶 作用下， 以 重水 为溶剂， 反应 3.0h， 以76%的产率得到2-[2-(2,6-dichlorophenyl)vinyl]quinolin-8-ol
  参考文献：
  名称：

  2-苯乙烯基喹啉衍生物的合成及其抗癌活性。p53独立的作用机制

  摘要：

  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。

  DOI：

  10.1016/j.ejmech.2019.05.061

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。
• 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.