7-chloro-N-(1H-indazol-6-yl)quinolin-4-amine | 50592-88-6

• 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-(1H-indazol-6-yl)quinolin-4-amine
• 英文别名: (7-chloro-quinolin-4-yl)-(1(2)H-indazol-6-yl)-amine；7-Chlor-4-(6-indazolamino)-chinolin；7-Chloro-N-1H-indazol-6-yl-4-quinolinamine
• CAS: 50592-88-6
• 化学式: C₁₆H₁₁ClN₄
• 分子量: 294.743
• InChiKey: JTJIUQOKVNYXAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 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：
  53.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-chloro-N-(1H-indazol-6-yl)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84%的产率得到3-chloro-7H,12H-pyrazolo[5,4-b]quinolino[3,2-c]indole
  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 、 6-氨基吲唑 以 neat (no solvent) 为溶剂， 120.0 ℃ 、200.0 kPa 条件下， 反应 0.17h， 以94%的产率得到7-chloro-N-(1H-indazol-6-yl)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

• US3755332A
  申请人：——

  公开号：US3755332A

  公开（公告）日：1973-08-28
• 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.