4-(4-aminoanilino)-6-(dimethylamino)quinolinium chloride | 1020087-16-4

• 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-(4-aminoanilino)-6-(dimethylamino)quinolinium chloride
• 英文别名: 4-N-(4-aminophenyl)-6-N,6-N-dimethylquinolin-1-ium-4,6-diamine;chloride
• CAS: 1020087-16-4
• 化学式: C₁₇H₁₈N₄*ClH
• 分子量: 314.818
• InChiKey: RWHYGYAFFWXQSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.05
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-aminoanilino)-6-(dimethylamino)quinolinium chloride 、 3-乙酰基苯甲酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以42%的产率得到4-{4-[(3-acetylbenzoyl)amino]anilino}-6-(dimethylamino)quinolinium chloride
  参考文献：
  名称：

  Structure–activity relationships for 4-anilinoquinoline derivatives as inhibitors of the DNA methyltransferase enzyme DNMT1

  摘要：

  A series of 4-anilinoquinoline derivatives related to the known inhibitor SGI-1027, containing side chains of varying pK(a), were prepared by acid-catalysed coupling of the pre-formed side chains with 4-chloroquinolines. The compounds were evaluated for their ability to reduce the level of DNMT1 protein in HCT116 human colon carcinoma cells by Western blotting. With a very strongly basic N-methylpyridinium side chain, only NHCO-linked compounds were effective, whereas less strongly basic ((diaminomethylene) hydrazono)ethyl or 3-methylpyrimidine-2,4-diamine side chains allowed both NHCO- and CONH-linked compounds to show activity. In contrast, the pK(a) of the quinoline unit had little apparent influence on activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.03.033
• 作为产物：
  描述：

  N-(4-{[6-(dimethylamino)-4-quinolinyl]amino}phenyl)acetamide 在 盐酸 、 水 作用下， 以 1,4-二氧六环 为溶剂， 以100%的产率得到4-(4-aminoanilino)-6-(dimethylamino)quinolinium chloride
  参考文献：
  名称：

  WO2008/46085

  摘要：

  公开号：

文献信息

• QUINOLINE DERIVATIVES FOR MODULATING DNA METHYLATION
  申请人：Phiasivongsa Pasit

  公开号：US20090285772A1

  公开（公告）日：2009-11-19

  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.

  提供了喹啉衍生物，特别是4-苯胺基喹啉衍生物。这样的喹啉衍生物可用于调节DNA甲基化，例如通过选择性抑制DNA甲基转移酶DNMT1，有效抑制C-5位置的胞嘧啶甲基化。提供了合成多种4-苯胺基喹啉衍生物和调节DNA甲基化的方法。还提供了制剂和给药这些化合物或组合物以治疗癌症和血液疾病的方法。
• Quinoline derivatives for modulating DNA methylation
  申请人：SuperGen, Inc.

  公开号：US07790746B2

  公开（公告）日：2010-09-07

  Quinoline derivatives, particularly 4-anilinoquinoline derivatives of formula (I), 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 DNMT 1. 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.

  提供了喹啉衍生物，特别是公式（I）的4-苯胺基喹啉衍生物：这样的喹啉衍生物可用于调节DNA甲基化，例如通过选择性抑制DNA甲基转移酶DNMT1，有效抑制C-5位点的胞嘧啶甲基化。提供了合成多种4-苯胺基喹啉衍生物和调节DNA甲基化的方法。还提供了制剂和给药这些化合物或组合物以治疗癌症和血液系统疾病的方法。
• US7790746B2
  申请人：——

  公开号：US7790746B2

  公开（公告）日：2010-09-07
• US7939546B2
  申请人：——

  公开号：US7939546B2

  公开（公告）日：2011-05-10
• [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.