7-chloro-N-(1-naphthalenyl)quinolin-4-amine

• 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: 7-chloro-N-(1-naphthalenyl)quinolin-4-amine
• 英文别名: 7-chloro-N-naphthalen-1-ylquinolin-4-amine
• 化学式: C₁₉H₁₃ClN₂
• 分子量: 304.779
• InChiKey: SQDUSAGFODETGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-chloro-N-(1-naphthalenyl)quinolin-4-amine 在 四丁基溴化铵 、 palladium diacetate 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以86%的产率得到3-chloro-13H-benzo[g]indolo[3,2-c]quinoline
  参考文献：
  名称：

  Palladium-catalyzed regioselective aerobic oxidative cyclization via C–H activation in chloroquine analogues: synthesis and cytotoxic study

  摘要：

  The intramolecular regioselective aerobic oxidative cyclization via two types of discrete C-H activation in 7-chloroquinoline analogues is described. All the synthesized compounds are screened against three human cancer cell lines (CCRF-CEM, HT29, and MCF7) for their anticancer activities. Among them, chloroquine analogues with naphthalene ring either substituted/fused form enhance remarkable cytotoxic activity against human breast adenocarcinoma cancer cell line (MCF-7) which outranged positive control doxorubicin. Similarly, 3-chloro-7H,12H-pyrazolo[5,4-b]quinolino[3,2-c]indole has possessed significant activity against all the tested cell lines and outranged activity against CCRF-CEM cell line.

  DOI：

  10.1007/s00706-015-1474-z
• 作为产物：
  描述：

  4,7-二氯喹啉 、 1-萘胺 以 neat (no solvent) 为溶剂， 120.0 ℃ 、200.0 kPa 条件下， 反应 0.17h， 以97%的产率得到7-chloro-N-(1-naphthalenyl)quinolin-4-amine
  参考文献：
  名称：

  Palladium-catalyzed regioselective aerobic oxidative cyclization via C–H activation in chloroquine analogues: synthesis and cytotoxic study

  摘要：

  The intramolecular regioselective aerobic oxidative cyclization via two types of discrete C-H activation in 7-chloroquinoline analogues is described. All the synthesized compounds are screened against three human cancer cell lines (CCRF-CEM, HT29, and MCF7) for their anticancer activities. Among them, chloroquine analogues with naphthalene ring either substituted/fused form enhance remarkable cytotoxic activity against human breast adenocarcinoma cancer cell line (MCF-7) which outranged positive control doxorubicin. Similarly, 3-chloro-7H,12H-pyrazolo[5,4-b]quinolino[3,2-c]indole has possessed significant activity against all the tested cell lines and outranged activity against CCRF-CEM cell line.

  DOI：

  10.1007/s00706-015-1474-z

文献信息

• N‐Heterocyclic Carbene/Cobalt Cooperative Catalysis for the Chemo‐ and Regioselective C−N Bond Formation between Aldehyde and Amines/Amides
  作者：Asher M. Siddiqui、Anam Khalid、Arif Khan、Chandra S. Azad、Mohd. Samim、Imran A. Khan

  DOI：10.1002/cctc.202000156

  日期：2020.9.4

  examples), tertiary amides (31 examples), and imides (16 examples) by a Cobalt(II) catalyzed oxidative amide coupling in aqueous media. The Co(III)‐TMC was reacted with N‐Heteroatom Carbene to form active catalyst Co(II)NHC‐TMC in situ which involves in the coordination with Breslow's intermediate and SET for the activation of aldehyde and amides. The mechanism for activation of amide and amine differs

  通过钴（II）在水性介质中催化氧化酰胺偶联反应构建各种仲（4个实例），叔酰胺（31个实例）和酰亚胺（16个实例）的新颖方法。Co（III）-TMC与N-Heteroatom Carbene反应形成原位活性催化剂Co（II）NHC-TMC ，该催化剂涉及与Breslow中间体和SET的配位，以活化醛和酰胺。酰胺和胺的活化机理分别基于基于SET的亲核加成和配体交换而不同。使用Fe（III）（EDTA）-H 2 O 2作为氧化剂可实现催化剂的再生。Co（II）TMC‐O 2的使用在该过程中也发现同样有效。发现该方法在存在同样敏感的邻-C-H键活化的情况下对NH活化具有区域选择性。发现胺比相应的酰胺更易受反应影响。
• Palladium-catalyzed regioselective aerobic oxidative cyclization via C–H activation in chloroquine analogues: synthesis and cytotoxic study
  作者：Gopal Senthil Kumar、Mohamed Ashraf Ali、Tan Soo Choon、Karnam Jayarampillai Rajendra Prasad

  DOI：10.1007/s00706-015-1474-z

  日期：2015.12

  The intramolecular regioselective aerobic oxidative cyclization via two types of discrete C-H activation in 7-chloroquinoline analogues is described. All the synthesized compounds are screened against three human cancer cell lines (CCRF-CEM, HT29, and MCF7) for their anticancer activities. Among them, chloroquine analogues with naphthalene ring either substituted/fused form enhance remarkable cytotoxic activity against human breast adenocarcinoma cancer cell line (MCF-7) which outranged positive control doxorubicin. Similarly, 3-chloro-7H,12H-pyrazolo[5,4-b]quinolino[3,2-c]indole has possessed significant activity against all the tested cell lines and outranged activity against CCRF-CEM cell line.