2-[4-[2-[4-aminophenyl]ethylamino]-6-([3-tert-butoxycarbonylaminophenyl]amino)[1,3,5]triazine-2-ylamino]ethanol | 1192801-07-2

• 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: 2-[4-[2-[4-aminophenyl]ethylamino]-6-([3-tert-butoxycarbonylaminophenyl]amino)[1,3,5]triazine-2-ylamino]ethanol
• 英文别名: 2-(4-(4-aminophenethylamino)-6-(3-(tert-butoxycarbonylamino)phenylamino)-1,3,5-triazin-2-ylamino)ethanol；tert-butyl N-[3-[[4-[2-(4-aminophenyl)ethylamino]-6-(2-hydroxyethylamino)-1,3,5-triazin-2-yl]amino]phenyl]carbamate
• CAS: 1192801-07-2
• 化学式: C₂₄H₃₂N₈O₃
• 分子量: 480.57
• InChiKey: MEAMAQSVZQQADB-UHFFFAOYSA-N

物化性质

• 熔点：
  154-155 °C
• 密度：
  1.347±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  159
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,4-dichloro-6-(3-fluorophenylamino)-1,3,5-triazine 、 2-[4-[2-[4-aminophenyl]ethylamino]-6-([3-tert-butoxycarbonylaminophenyl]amino)[1,3,5]triazine-2-ylamino]ethanol 在 碳酸氢钠 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 生成
  参考文献：
  名称：

  2,4,6-Trisubstituted Triazines as Protein A Mimetics for the Treatment of Autoimmune Diseases

  摘要：

  A first-in-class series of low molecular weight trisubstituted triazines were synthesized and evaluated for their ability to mimic protein A binding to human IgG antibody. The structure-activity relationship (SAR) demonstrates that the 1,3-phenylenediamine component was essential for robust activity. Twenty-two compounds, represented by lead molecule 34, displayed significant activity compared to protein A. These compounds may prove useful for the treatment of autoimmune disease.

  DOI：

  10.1021/jm901403r
• 作为产物：
  描述：

  2-(4-氨基苯)乙胺 、 2-(4-(3-(tert-butoxycarbonylamino)phenylamino)-6-chloro-1,3,5-triazin-2-ylamino)ethanol 以 四氢呋喃 为溶剂， 以81%的产率得到2-[4-[2-[4-aminophenyl]ethylamino]-6-([3-tert-butoxycarbonylaminophenyl]amino)[1,3,5]triazine-2-ylamino]ethanol
  参考文献：
  名称：

  2,4,6-Trisubstituted Triazines as Protein A Mimetics for the Treatment of Autoimmune Diseases

  摘要：

  A first-in-class series of low molecular weight trisubstituted triazines were synthesized and evaluated for their ability to mimic protein A binding to human IgG antibody. The structure-activity relationship (SAR) demonstrates that the 1,3-phenylenediamine component was essential for robust activity. Twenty-two compounds, represented by lead molecule 34, displayed significant activity compared to protein A. These compounds may prove useful for the treatment of autoimmune disease.

  DOI：

  10.1021/jm901403r

文献信息

• An Efficient Kilogram-Scale Synthesis of <i>N</i>,<i>N</i>′-Bis(4,6-disubstituted 1,3,5-triazin-2-yl)-4-aminophenetylamine
  作者：Jean-Simon Duceppe、Valérie Perron、Josée Cloutier、Christopher Penney、Boulos Zacharie

  DOI：10.1021/op900202b

  日期：2009.11.20

  A practical large-scale synthesis was developed for the preparation of N,N′-bis(4,6-disubstituted 1,3,5-triazin-2-yl)-4-aminophenethylamine derivatives exemplified by compound 2. This route is a six-step procedure starting from commercially available cyanuric chloride and 3-(tert-butoxycarbonylamino) aniline based on the reactivity differences of the three chlorine atoms on the triazine ring. The optimized

  开发了一种实用的大规模合成方法，用于制备以化合物2为例的N，N′-双（4,6-二取代的1,3,5-三嗪-2-基）-4-氨基苯乙胺衍生物。基于三嗪环上三个氯原子的反应性差异，该途径是六步过程，从市售的氰尿酰氯和3-（叔丁氧基羰基氨基）苯胺开始。按比例扩大优化程序，以最终产品2的总收率达到61％和99.9％的纯度。这些低分子量化合物模拟蛋白质A与IgG抗体结合的能力。