4-chloro-N,N,2-trimethylquinolin-7-amine | 114058-83-2

• 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: 4-chloro-N,N,2-trimethylquinolin-7-amine
• 英文别名: 7-Quinolinamine, 4-chloro-N,N,2-trimethyl-
• CAS: 114058-83-2
• 化学式: C₁₂H₁₃ClN₂
• 分子量: 220.702
• InChiKey: DWXPSBGKEMNITB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  16.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-chloro-N,N,2-trimethylquinolin-7-amine 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 以84%的产率得到7-(N,N-dimethylamino)quinaldine
  参考文献：
  名称：

  7-Aminoquinolines. A novel class of agents active against herpes viruses

  摘要：

  A series of 7-aminoquinoline derivatives was synthesized and evaluated for their capacity to produce cytotoxicity in KB cells and to inhibit the replication of herpes simplex virus (HSV) type 1. All compounds tested inhibited the replication of HSV-1 with 50% inhibitory concentrations in the range of 2-50 micrograms/mL. The antiviral activity of many compounds, however, was separated from cytotoxicity to replicating uninfected cells by only two- to fivefold higher than those required for antiviral activity. Nonetheless, six compounds (10, 28, 29, 32, 34, and 36) were identified in which the separation was greater than fivefold. All compounds examined were more potent inhibitors of viral DNA synthesis than the cellular DNA synthesis.

  DOI：

  10.1021/jm00402a016
• 作为产物：
  描述：

  7-(dimethylamino)-2-methyl-4(1H)-quinolone 在 三氯氧磷 作用下， 反应 1.0h， 以76%的产率得到4-chloro-N,N,2-trimethylquinolin-7-amine
  参考文献：
  名称：

  7-Aminoquinolines. A novel class of agents active against herpes viruses

  摘要：

  A series of 7-aminoquinoline derivatives was synthesized and evaluated for their capacity to produce cytotoxicity in KB cells and to inhibit the replication of herpes simplex virus (HSV) type 1. All compounds tested inhibited the replication of HSV-1 with 50% inhibitory concentrations in the range of 2-50 micrograms/mL. The antiviral activity of many compounds, however, was separated from cytotoxicity to replicating uninfected cells by only two- to fivefold higher than those required for antiviral activity. Nonetheless, six compounds (10, 28, 29, 32, 34, and 36) were identified in which the separation was greater than fivefold. All compounds examined were more potent inhibitors of viral DNA synthesis than the cellular DNA synthesis.

  DOI：

  10.1021/jm00402a016

文献信息

• Substituent Effects on the Sensitivity of a Quinoline Photoremovable Protecting Group to One- and Two-Photon Excitation
  作者：M. Jarrett Davis、Christopher H. Kragor、Khalilah G. Reddie、Hunter C. Wilson、Yue Zhu、Timothy M. Dore

  DOI：10.1021/jo802658a

  日期：2009.2.20

  Photoremovable protecting groups that can reveal biologically important functional groups through one- and two-photon excitation (1PE and 2PE, respectively) have promise in regulating physiological function in a temporally and spatially restricted manner. Only a few chromophores have sufficient sensitivity to 2PE suitable for use as “caging groups” in physiology experiments. It would be useful to develop

  可以通过单光子和双光子激发（分别为1PE和2PE）激发出生物学上重要的官能团的可光去除保护基团，有望在时间和空间上限制其生理功能。只有少数生色团对2PE具有足够的敏感性，适合用作生理学实验中的“笼型基团”。建立发色团的结构-性质关系，使具有高双光子解开作用截面（δu的发色团）的发色团将是有用的。）可以设计。8-溴-7-羟基喹啉基生色团（BHQ）通过1PE和2PE释放各种官能团。将溴取代基交换为硝基（NHQ），氰基（CyHQ）或氯（CHQ）或将羟基交换为二甲氨基（DMAQ和DMAQ-Cl）或巯基（TQ）会显着改变喹啉发色团的光化学和光物理性质。CyHQ-OAc对乙酸盐释放的敏感性提高了3倍，而NHQ-OAc对光化学不敏感。量子效率（Q û）的氨基和巯基衍生物比BHQ-OAc低约一个数量级。与BHQ-OAc相比，所有生色团均显示出对2PE的敏感性降低，但CyHQ，DMAQ和DMAQ-Cl生色团
• BHQ-CAGED NUCLEOTIDE PROBES PHOTOLYSABLE BY TWO-PHOTON EXCITATION
  申请人：Dore Timothy M.

  公开号：US20100048502A1

  公开（公告）日：2010-02-25

  The disclosure encompasses caged compounds such as caged nucleoside phosphoesters (caged nucleotides). In an embodiment, the caged nucleotides include compounds corresponding to those described by formula (I) that may be activated by two-photon excitation, and methods of synthesis of such compounds. 8-Bromo-7-hydroxyquinoline-caged ATP was synthesized and examined for its photochemistry as a biologically useful, temporally and spatially controlled ATP-releasing reagent. The combination of two-photon excitation hydrolysis and activation of caged ATP enables methods for finely focusing ATP activation at the sub-cellular level or to a greater depth of activation, thereby providing improved resolution of ATP-dependent processes at the cellular level.

  该披露涵盖了笼状化合物，例如笼状核苷酸磷酸酯（笼状核苷酸）。在一种实施方案中，笼状核苷酸包括与公式（I）描述的化合物相对应的化合物，可以通过双光子激发激活，并提供了这种化合物的合成方法。合成了8-溴-7-羟基喹啉笼状ATP，并对其光化学性质进行了检查，作为一种生物学上有用的、时间和空间可控的ATP释放试剂。双光子激发水解和笼状ATP的激活相结合，可以在亚细胞水平或更深的激活深度上精细地聚焦ATP的激活，从而提供了更好的细胞水平上ATP依赖过程的分辨率。
• NASR, M.;DRACH, J. C.;SMITH, S. H.;SHIPMAN, CH. , (JR);BURCKHALTER, J. H., J. MED. CHEM., 31,(1988) N 7, C. 1347-1351
  作者：NASR, M.、DRACH, J. C.、SMITH, S. H.、SHIPMAN, CH. , (JR)、BURCKHALTER, J. H.

  DOI：——

  日期：——
• US8173620B2
  申请人：——

  公开号：US8173620B2

  公开（公告）日：2012-05-08
• 7-Aminoquinolines. A novel class of agents active against herpes viruses
  作者：Mohamed Nasr、John C. Drach、Sandra H. Smith、Charles Shipman、J. H. Burckhalter

  DOI：10.1021/jm00402a016

  日期：1988.7

  A series of 7-aminoquinoline derivatives was synthesized and evaluated for their capacity to produce cytotoxicity in KB cells and to inhibit the replication of herpes simplex virus (HSV) type 1. All compounds tested inhibited the replication of HSV-1 with 50% inhibitory concentrations in the range of 2-50 micrograms/mL. The antiviral activity of many compounds, however, was separated from cytotoxicity to replicating uninfected cells by only two- to fivefold higher than those required for antiviral activity. Nonetheless, six compounds (10, 28, 29, 32, 34, and 36) were identified in which the separation was greater than fivefold. All compounds examined were more potent inhibitors of viral DNA synthesis than the cellular DNA synthesis.