4-[(2-amino-6-methyl-4-pyrimidinyl)amino]-N-(4-aminophenyl)benzamide | 32567-74-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-[(2-amino-6-methyl-4-pyrimidinyl)amino]-N-(4-aminophenyl)benzamide
• 英文别名: 4-(2-amino-6-methyl-pyrimidin-4-ylamino)-N-(4-amino-phenyl)-benzamide；2-Amino-4--6-methyl-pyrimidin；4-[(2-amino-6-methylpyrimidin-4-yl)amino]-N-(4-aminophenyl)benzamide
• CAS: 32567-74-1
• 化学式: C₁₈H₁₈N₆O
• 分子量: 334.381
• InChiKey: YDAJZDXRALGOEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  119
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-氯-6-硝基喹啉 、 4-[(2-amino-6-methyl-4-pyrimidinyl)amino]-N-(4-aminophenyl)benzamide 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以87%的产率得到4-[(2-amino-6-methyl-4-pyrimidinyl)amino]-N-{4-[(6-nitro-4-quinolinyl)amino]phenyl}benzamide dihydrochloride
  参考文献：
  名称：

  WO2008/46085

  摘要：

  公开号：
• 作为产物：
  描述：

  2-氨基-4-氯-6-甲基嘧啶 在 盐酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 乙二醇乙醚 、 水 为溶剂， 反应 3.67h， 生成 4-[(2-amino-6-methyl-4-pyrimidinyl)amino]-N-(4-aminophenyl)benzamide
  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

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 SERVANT À MODULER LA MÉTHYLATION DE L'ADN
  申请人：SUPERGEN INC

  公开号：WO2009049132A1

  公开（公告）日：2009-04-16

  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.