N7,N7-dimethylquinoline-2,7-diamine | 114058-68-3

• 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: N7,N7-dimethylquinoline-2,7-diamine
• 英文别名: 2,7-Quinolinediamine, N7,N7-dimethyl-；7-N,7-N-dimethylquinoline-2,7-diamine
• CAS: 114058-68-3
• 化学式: C₁₁H₁₃N₃
• 分子量: 187.244
• InChiKey: MBFDRIJGUMKXRG-UHFFFAOYSA-N

物化性质

• 熔点：
  140-142 °C(Solv: hexane (110-54-3))
• 沸点：
  374.2±27.0 °C(Predicted)
• 密度：
  1.192±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-chloro-7-(dimethylamino)quinoline 在 氨 、 苯酚 作用下， 反应 6.0h， 以30%的产率得到N7,N7-dimethylquinoline-2,7-diamine
  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

• One-pot synthesis of 2-aminoquinoline-based alkaloids from acetonitrile
  作者：Takashi Tomioka、Yusuke Takahashi、Toshihide Maejima

  DOI：10.1039/c2ob25709b

  日期：——

  α-Diaminoboryl carbanions, readily prepared from acetonitrile, stereoselectively convert 2-nitrobenzaldehydes into nitrophenyl (Z)-acrylonitriles. Subsequent reductive cyclization leads to a series of 2-aminoquinoline derivatives. The entire procedure is practically operated in a single flask.

  α-二氨基硼基碳负离子可以通过简便的方法从乙腈中制备，具有立体选择性地将2-硝基苯甲醛转化为硝基苯（Z）-丙烯腈。随后进行还原环化反应，得到一系列2-氨基喹啉衍生物。整个过程几乎可以在一个烧瓶中完成。
• 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：——
• 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.