4-((2-amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-ylamino)methyl)benzoic acid | 1196994-20-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 4-((2-amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-ylamino)methyl)benzoic acid
• 英文别名: 4-[[[2-amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]amino]methyl]benzoic acid
• CAS: 1196994-20-3
• 化学式: C₁₇H₂₂N₆O₂
• 分子量: 342.401
• InChiKey: BISUKAQGRPXHOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  N-甲基哌嗪 、 4-[[(2-Amino-6-chloropyrimidin-4-yl)amino]methyl]benzoic acid 在 N,N-二异丙基乙胺 作用下， 以 异丙醇 为溶剂， 生成 4-((2-amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-ylamino)methyl)benzoic acid
  参考文献：
  名称：

  2,4-Diaminopyrimidines as histamine H4 receptor ligands—Scaffold optimization and pharmacological characterization

  摘要：

  The human histamine H-4 receptor (hH(4)R) is a promising new target in the therapy of inflammatory diseases and disorders of the immune system. For the development of new H4R antagonists a broad ligand-based virtual screening was performed resulting in two hits. The dissection of their common annelated aromatic core into its heteromonocyclic components showed that 2,4-diaminopyrimidine is a potent hH(4)R affinity scaffold, which was comprehensively investigated. Structure-activity relationship studies revealed that slight structural changes evoke extensive differences in functional activities and potencies: while o-and p-substituted benzyl amines mainly showed partial agonism, m-substituted and rigidified ones exhibited inverse agonist efficacy. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.08.059

文献信息

• 2,4-Diaminopyrimidines as histamine H4 receptor ligands—Scaffold optimization and pharmacological characterization
  作者：Kerstin Sander、Tim Kottke、Yusuf Tanrikulu、Ewgenij Proschak、Lilia Weizel、Erich H. Schneider、Roland Seifert、Gisbert Schneider、Holger Stark

  DOI：10.1016/j.bmc.2009.08.059

  日期：2009.10

  The human histamine H-4 receptor (hH(4)R) is a promising new target in the therapy of inflammatory diseases and disorders of the immune system. For the development of new H4R antagonists a broad ligand-based virtual screening was performed resulting in two hits. The dissection of their common annelated aromatic core into its heteromonocyclic components showed that 2,4-diaminopyrimidine is a potent hH(4)R affinity scaffold, which was comprehensively investigated. Structure-activity relationship studies revealed that slight structural changes evoke extensive differences in functional activities and potencies: while o-and p-substituted benzyl amines mainly showed partial agonism, m-substituted and rigidified ones exhibited inverse agonist efficacy. (C) 2009 Elsevier Ltd. All rights reserved.