2-chloro-7-(dimethylamino)quinoline | 114058-67-2

• 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: 2-chloro-7-(dimethylamino)quinoline
• 英文别名: 7-Quinolinamine, 2-chloro-N,N-dimethyl-；2-chloro-N,N-dimethylquinolin-7-amine
• CAS: 114058-67-2
• 化学式: C₁₁H₁₁ClN₂
• 分子量: 206.675
• InChiKey: UJGAEGLRTGDXQZ-UHFFFAOYSA-N

物化性质

• 熔点：
  105-107 °C(Solv: hexane (110-54-3))
• 沸点：
  342.5±27.0 °C(Predicted)
• 密度：
  1.239±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 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：
  16.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  7-(Dimethylamino)carbostyril 在 镍 盐酸 、 氢氧化钾 、 氢气 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 2-chloro-7-(dimethylamino)quinoline
  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

• 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：——
• QUINOLINE DERIVATIVES FOR MODULATING DNA METHYLATION
  申请人：SuperGen, Inc.

  公开号：EP2078008A2

  公开（公告）日：2009-07-15
• [EN] QUINOLINE DERIVATIVES FOR MODULATING DNA METHYLATION<br/>[FR] DÉRIVÉS DE QUINOLINE POUR LA MODULATION DE LA MÉTHYLATION DE L'ADN
  申请人：SUPERGEN INC

  公开号：WO2008046085A2

  公开（公告）日：2008-04-17

  [EN] Quinoline derivatives, particularly 4-anilinoquinoline derivatives, are provided. Such quinoline derivatives can be used for modulation of DNA methylation, such as effective inhibition of methylation of cytosine at the C-5 position, for example via selective inhibition of DNA methyltransferase DNMT1. Methods for synthesizing numerous 4-anilinoquinoline derivatives and for modulating DNA methylation are provided. Also provided are methods for formulating and administering these compounds or compositions to treat conditions such as cancer and hematological disorders.
  [FR] L'invention concerne des dérivés de quinoline, notamment des dérivés de 4-anilinoquinoline. De tels dérivés de quinoline peuvent être utilisés pour la modulation de la méthylation de l'ADN, telle que l'inhibition effective de la méthylation de la cytosine à la position C-5, par exemple par inhibition sélective de la méthyltransférase de l'ADN DNMT1. L'invention concerne également des procédés de synthèses de nombreux dérivés de 4-anilinoquinoline et de modulation de la méthylation de l'ADN. L'invention concerne également des procédés de formulation et d'administration de ces composés ou compositions pour traiter des maladies telles que le cancer et les troubles hématologiques.
• 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.