3-phenylquinolin-8-amine | 190137-71-4

• 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: 3-phenylquinolin-8-amine
• 英文别名: 3-phenyl-[8]quinolylamine；3-Phenyl-[8]chinolylamin
• CAS: 190137-71-4
• 化学式: C₁₅H₁₂N₂
• 分子量: 220.274
• InChiKey: HGXHJJCCMSMDHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-phenylquinolin-8-amine 在 磷酸 、 砷酸、原砷酸 、 丙烯醛 作用下， 生成 3-phenyl-1,10-phenanthroline
  参考文献：
  名称：

  SUBSTITUTED 1,10-PHENANTHROLINES. VIII. 2- AND 3-PHENYL DERIVATIVES¹

  摘要：

  DOI：

  10.1021/jo01127a006
• 作为产物：
  描述：

  1,3-dichloro-2-phenylpropan-2-ol 在 乙醇 、 sodium acetate 、 铁粉 、 溶剂黄146 作用下， 生成 3-phenylquinolin-8-amine
  参考文献：
  名称：

  SUBSTITUTED 1,10-PHENANTHROLINES. VIII. 2- AND 3-PHENYL DERIVATIVES¹

  摘要：

  DOI：

  10.1021/jo01127a006

文献信息

• Design, Synthesis, and Evaluation in Vitro of Quinoline-8-carboxamides, a New Class of Poly(adenosine-diphosphate-ribose)polymerase-1 (PARP-1) Inhibitor
  作者：Anna-Marie Lord、Mary F. Mahon、Matthew D. Lloyd、Michael D. Threadgill

  DOI：10.1021/jm8013629

  日期：2009.2.12

  prepared by selective Pd-catalyzed couplings at the 2-position of 2,8-dibromoquinoline, followed by lithium−bromine exchange of the intermediate 2-(alkyl/aryl)-8-bromoquinolines and reaction with trimethylsilyl isocyanate. The intramolecular hydrogen bond was confirmed by X-ray and by NMR. The SAR of the 3-substituted compounds for inhibition of human recombinant PARP-1 activity showed a requirement

  聚（ADP-核糖）聚合酶-1是药物设计中的重要目标酶。抑制剂具有多种治疗活性。设计了一系列喹啉-8-羧酰胺以通过分子内氢键维持所需的药效团构象。通过Pd催化的偶联（Suzuki，Sonogashira，Stille）与3-碘喹啉-8-羧酰胺合成3-取代的喹啉-8-羧酰胺，这是在最后一步引入多样性的有效方法。通过在2,8-二溴喹啉的2-位进行选择性Pd催化偶联反应，然后通过中间体2-（烷基/芳基）-8-溴喹啉的锂溴交换和反应制备2-取代的喹啉-8-甲酰胺。与异氰酸三甲基甲硅烷基酯。分子内氢键通过X射线和NMR确认。用于抑制人重组PARP-1活性的3-取代化合物的SAR显示需要一个小的狭窄基团。2位取代基增加了效能，最活跃的2-甲基喹啉-8-羧酰胺具有IC50 = 500 nM（5-氨基异喹啉-1-酮（5-AIQ，标准水溶性抑制剂）的IC 50 = 1.8μM）。
• Copper(<scp>ii</scp>)-catalyzed C5 and C7 halogenation of quinolines using sodium halides under mild conditions
  作者：Jun Xu、Xiaolei Zhu、Guobin Zhou、Beibei Ying、Pingping Ye、Lingying Su、Chao Shen、Pengfei Zhang

  DOI：10.1039/c6ob00169f

  日期：——

  A simple and mild protocol for copper catalyzed halogenation of quinoline at C5 and C7 positions was developed, affording the desired remote C–H activation products in moderate to good yields. This reaction proceeds with low-cost sodium halides (NaX, X = Cl, Br, I) and features excellent substrate tolerance. A series of control experiments were carried out to illustrate a single-electron-transfer process

  开发了一种简单温和的方案，用于铜在C5和C7位置上催化喹啉卤化，从而以中等到良好的产率提供了所需的远程C–H活化产物。该反应以低成本的卤化钠（NaX，X = Cl，Br，I）进行，并具有出色的底物耐受性。进行了一系列对照实验，以说明在卤化中起至关重要作用的单电子转移过程。
• Site-selective C5–H and <i>N</i>–H alkylation of unprotected 8-aminoquinolines
  作者：Ozge Turbedaroglu、Ferruh Lafzi、Haydar Kilic

  DOI：10.1039/d2cc00780k

  日期：——

  We report a highly site-selective direct C5–H and N–H alkylation of free amine group-bearing 8-aminoquinolines in high to excellent yields.

  我们报道了一种高度位点选择性的直接C5-H和N-H烷基化自由胺基8-氨基喹啉的方法，产率高至极好。
• Ruthenium-Catalyzed Difluoroalkylation of 8-Aminoquinoline Amides at the C5-Position
  作者：Changpeng Chen、Runsheng Zeng、Jingyu Zhang、Yingsheng Zhao

  DOI：10.1002/ejoc.201701150

  日期：2017.12.15

  A ruthenium‐catalyzed highly selective difluoromethylation of 8‐aminoquinoline amides at the C5 position has been developed. It tolerates a broad range of functional groups, providing the corresponding difluoromethylated products in moderate to good yields. Preliminary experimental results indicate that the tricoordinate ruthenium intermediate is the key factor in achieving the C5‐position selectivity.
• Effect of 3-subsitution of quinolinehydroxamic acids on selectivity of histone deacetylase isoforms
  作者：Samir Mehndiratta、Mei-Chuan Chen、Yuh-Hsuan Chao、Cheng-Hsin Lee、Jing-Ping Liou、Mei-Jung Lai、Hsueh-Yun Lee

  DOI：10.1080/14756366.2020.1839446

  日期：2021.1.1

  A series of 3-subsituted quinolinehydroxamic acids has been synthesised and evaluated for their effect on human lung cancer cell line (A549), human colorectal cancer cell line (HCT116) and HDAC isoforms 1, 2, 6, and 8. The results indicated that substitution at C3 of quinoline is favoured for HDAC6 selectivity. Two compounds (25 and 26) were also found to be potent anti-proliferative compounds with IC50 values ranging from 1.29 to 2.13 mu M against A549 and HCT116 cells. These compounds displayed remarkable selectivity for HDAC6 over other HDAC isoforms with nanomolar IC50 values. Western blot analysis revealed that compounds of this series activate apoptotic caspase pathway as indicated by cleavage of caspase 3, 8, and 9 and also increase phosphorylated H2AX thus inducing DNA double strand fragmentation in a concentration dependent manner. Flow cytometric analysis also displayed a dose dependent increase of cell population in sub G1 phase.