2,6-diisopropyl-N-(quinolin-2-ylmethylene)aniline | 220001-08-1

• 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: 2,6-diisopropyl-N-(quinolin-2-ylmethylene)aniline
• 英文别名: (E)-N-[2,6-Di(propan-2-yl)phenyl]-1-(quinolin-2-yl)methanimine；N-[2,6-di(propan-2-yl)phenyl]-1-quinolin-2-ylmethanimine
• CAS: 220001-08-1
• 化学式: C₂₂H₂₄N₂
• 分子量: 316.446
• InChiKey: OLRCJCNSYVAKAU-UHFFFAOYSA-N

物化性质

• 沸点：
  489.4±40.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  25.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  potassium tetrachloroplatinate(II) 、 2,6-diisopropyl-N-(quinolin-2-ylmethylene)aniline 以 甲醇 、 水 为溶剂， 反应 15.0h， 以75%的产率得到dichloro-[2-(2,6-diisopropylphen yl)iminomethylquinoline]platinum(II)
  参考文献：
  名称：

  Imino-quinolyl palladium(II) and platinum(II) complexes: Synthesis, characterization, molecular structures and cytotoxic effect

  摘要：

  Imino-quinolyl ligands L1-L5 were synthesized by condensation reaction sand obtained in good yields. Reactions of the ligands with either PdCl2(cod) or K-2[PtCl4] gave the corresponding palladium(II) and platinum(II) complexes 1-10 also in good yields. All the compounds were characterized by elemental analysis, IR, H-1 and C-13 NMR spectroscopy. X-ray crystallography was used to confirm the structures of these compounds. Molecular structures of 3 and 5 showed that the ligands coordinate to the metal center through the two nitrogen atoms, generating a distorted square planar geometry around the palladium atom. The new complexes exhibited remarkable cytotoxic activities against MCF-7 and HT-29 cancer cell lines. (C) 2013 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2013.02.029
• 作为产物：
  描述：

  喹啉-2-甲醛 、 2,6-二异丙基苯胺 在 甲酸 作用下， 以 甲醇 为溶剂， 以95%的产率得到2,6-diisopropyl-N-(quinolin-2-ylmethylene)aniline
  参考文献：
  名称：

  包含对癌细胞具有选择性毒性的N ^ N螯合的氨基吡啶基配体的半三明治钌（II）配合物

  摘要：

  化学疗法由于对癌细胞的选择性比正常细胞差而受到限制。在这里，我们设计了半三明治钌亚氨基吡啶基复合物[（η6-bz）Ru（N ^ N）Cl] PF6，以实现对癌细胞的选择性细胞毒性。这种钌配合物具有独特的特性，值得在新的抗癌药物设计中进行进一步的探索。

  DOI：

  10.1039/c7cc08270c

文献信息

• Novel half-sandwich iridium(<scp>iii</scp>) imino-pyridyl complexes showing remarkable <i>in vitro</i> anticancer activity
  作者：JuanJuan Li、Lihua Guo、Zhenzhen Tian、Meng Tian、Shumiao Zhang、Ke Xu、Yuchuan Qian、Zhe Liu

  DOI：10.1039/c7dt03265j

  日期：——

  antiproliferative activity towards A549 and Hela cancer cells, except for Cp* complex 1A towards Hela cells. Cpxbiph complex 2B displayed the highest potency, about 19× and 6× times more active than the clinical used drug cisplatin toward A549 and Hela cells, respectively. These complexes undergo hydrolysis and the kinetics data were calculated. DNA binding has been studied by interaction with nucleobases 9-ethylguanine

  七个新颖的半三明治IrIII环戊二烯基络合物[（η5-Cpx）Ir（N ^ N）Cl] PF6，其中Cpx为Cp *，或联苯衍生物Cpxbiph（C5Me4C6H4C6H5），N ^ N螯合配体为亚氨基吡啶基已经制备并表征了希夫碱配体。已经确定了配合物2A，2B和3A的X射线晶体结构。令人兴奋的是，除了Cp *复合物1A对Hela细胞外，所有七个复合物1A-4B对A549和Hela癌细胞均显示出有效的抗增殖活性。Cpxbiph复合物2B对A549和Hela细胞的效力最高，分别是临床使用的顺铂药物的19倍和6倍。这些配合物进行水解，并计算动力学数据。已通过与9-乙基鸟嘌呤和9-甲基腺嘌呤核苷相互作用，质粒DNA裂解，以及与ctDNA的相互作用。与DNA的相互作用似乎不是主要的作用机理。蛋白结合（牛血清白蛋白，牛血清白蛋白）已通过紫外可见，荧光和同步光谱研究建立。评价了复合物2B在GSH存在下
• Zwitterionic and cationic half-sandwich iridium(<scp>iii</scp>) ruthenium(<scp>ii</scp>) complexes bearing sulfonate groups: synthesis, characterization and their different biological activities
  作者：Yanjing Yang、Xingxing Ge、Lihua Guo、Teng Zhu、Zhenzhen Tian、Hairong Zhang、Qing Du、Hongwei Peng、Wenli Ma、Zhe Liu

  DOI：10.1039/c9dt00259f

  日期：——

  iridium(III) and ruthenium(II) complexes showed that the charge and the substitution pattern of the bidentate ligands, as well as the nature of the accompanying counteranion have a significant effect on their biological activities. In this contribution, a series of zwitterionic and cationic half-sandwich iridium(III) and ruthenium(II) complexes containing sulfonate groups have been prepared and characterized

  先前对中性和阳离子半三明治铱（III）和钌（II）配合物的研究表明，双齿配体的电荷和取代方式以及随附的抗衡阴离子的性质对其生物活性具有重要影响。在此贡献中，一系列两性离子和阳离子半三明治铱（III）和钌（II）已制备并表征了具有磺酸根基团的配合物。这两种复合物之间抗衡阴离子的不同位置对癌细胞的细胞毒活性产生很大影响。通过流式细胞术确定复合物的各种可能的作用机理（MoAs）。这项工作首次显示了两性离子和阳离子半三明治复合物之间的不同生物活性。
• Half-sandwich ruthenium(<scp>ii</scp>) complexes containing N^N-chelated imino-pyridyl ligands that are selectively toxic to cancer cells
  作者：Meng Tian、Juanjuan Li、Shumiao Zhang、Lihua Guo、Xiangdong He、Deliang Kong、Hairong Zhang、Zhe Liu

  DOI：10.1039/c7cc08270c

  日期：——

  Chemotherapy is limited by the poor selectivity towards cancer cells over normal cells. Herein, we designed half-sandwich ruthenium imino-pyridyl complexes [(η6-bz)Ru(N^N)Cl]PF6 to achieve selective cytotoxicity to cancer cells. This kind of ruthenium complexes has unique characteristics and is worthy of further exploration in the design of new anticancer drugs.

  化学疗法由于对癌细胞的选择性比正常细胞差而受到限制。在这里，我们设计了半三明治钌亚氨基吡啶基复合物[（η6-bz）Ru（N ^ N）Cl] PF6，以实现对癌细胞的选择性细胞毒性。这种钌配合物具有独特的特性，值得在新的抗癌药物设计中进行进一步的探索。
• Lysosome-Targeted Chemotherapeutics: Half-Sandwich Ruthenium(II) Complexes That Are Selectively Toxic to Cancer Cells
  作者：Zhenzhen Tian、Juanjuan Li、Shumiao Zhang、Zhishan Xu、Yuliang Yang、Deliang Kong、Hairong Zhang、Xingxing Ge、Junming Zhang、Zhe Liu

  DOI：10.1021/acs.inorgchem.8b01944

  日期：2018.9.4

  Poor selectivity between cancer cells and normal cells is one of the major limitations of cancer chemotherapy. Lysosome-targeted ruthenium-based complexes target tumor cells selectively, only displaying rather weak cytotoxicity or inactivity toward normal cells. Confocal microscopy was employed for the first time to determine the cellular localization of the half-sandwich Ru complex.

  癌细胞与正常细胞之间的选择性差是癌症化学疗法的主要限制之一。溶酶体靶向的钌基复合物选择性地靶向肿瘤细胞，仅表现出对正常细胞相当弱的细胞毒性或无活性。首次使用共聚焦显微镜来确定半三明治Ru复合物的细胞定位。
• Copper-catalyzed benzylic oxidation of C(sp3)–H bonds
  作者：Bo Zhang、Shou-Fei Zhu、Qi-Lin Zhou

  DOI：10.1016/j.tet.2012.12.046

  日期：2013.2

  A selective oxidation of benzylic C(sp3)–H bonds to C(sp3)–O bonds catalyzed by copper complexes of quinoline–imine ligands was developed with peresters as oxidants under mild reaction conditions, which converted benzylic methylenes directly into benzylic alcohols and esters by means of direct C–H bond functionalization.

  在温和的反应条件下，用过酸酯作为氧化剂，开发了由喹啉-亚胺配体的铜配合物催化的苄基C（sp 3）-H键到C（sp 3）-O键的选择性氧化。和酯通过直接的C–H键官能化来实现。