2-{3-[4-(benzyloxy)phenyl]propyl}-4-[(3-methylphenyl)amino]pyrimidine-5-carboxylic acid | 919486-32-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-{3-[4-(benzyloxy)phenyl]propyl}-4-[(3-methylphenyl)amino]pyrimidine-5-carboxylic acid
• CAS: 919486-32-1
• 化学式: C₂₈H₂₇N₃O₃
• 分子量: 453.541
• InChiKey: GAGNKURPMYCYGH-UHFFFAOYSA-N

物化性质

• 沸点：
  648.5±55.0 °C(Predicted)
• 密度：
  1.240±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.98
• 重原子数：
  34.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  84.34
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-{3-[4-(benzyloxy)phenyl]propyl}-4-[(3-methylphenyl)amino]pyrimidine-5-carboxylic acid 在 palladium on activated charcoal ammonium hydroxide 、 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 2-[3-(4-Hydroxyphenyl)propyl]-4-(3-methylanilino)pyrimidine-5-carboxamide
  参考文献：
  名称：

  Synthesis and evaluation of 2-{[2-(4-hydroxyphenyl)-ethyl]amino}pyrimidine-5-carboxamide derivatives as novel STAT6 inhibitors

  摘要：

  The STAT6 (signal transducers and activators of transcription 6) protein is activated by interleukin (IL)-4 and IL-13, and plays an important role in T-helper cell 2 (Th2) differentiation. STAT6 might therefore be an excellent therapeutic target for various allergic conditions, including asthma and atopic diseases. We synthesized a series of 2-{[2-(4-hydroxyphenyl)ethyl]amino}pyrimidine-5-carboxamide derivatives and evaluated their STAT6 inhibitory activities. Among these compounds, 4-(benzylamino)-2-{[2-(3-chloro-4-hydroxyphenyl)ethyl]amino}pyrimidine-5-carboxamide (2t, AS1517499) showed potent STAT6 inhibition with an IC50 value of 21 nM, and also inhibited IL-4-induced Th2 differentiation of mouse spleen T cells with an IC50 value of 2.3 nM and without influencing T-helper cell 1 (Th1) differentiation induced by IL-12. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.10.015
• 作为产物：
  描述：

  ethyl 2-{3-[4-(benzyloxy)phenyl]propyl}-4-chloropyrimidine-5-carboxylate 在 sodium hydroxide 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醇 、 乙腈 为溶剂， 反应 18.0h， 生成 2-{3-[4-(benzyloxy)phenyl]propyl}-4-[(3-methylphenyl)amino]pyrimidine-5-carboxylic acid
  参考文献：
  名称：

  Synthesis and evaluation of 2-{[2-(4-hydroxyphenyl)-ethyl]amino}pyrimidine-5-carboxamide derivatives as novel STAT6 inhibitors

  摘要：

  The STAT6 (signal transducers and activators of transcription 6) protein is activated by interleukin (IL)-4 and IL-13, and plays an important role in T-helper cell 2 (Th2) differentiation. STAT6 might therefore be an excellent therapeutic target for various allergic conditions, including asthma and atopic diseases. We synthesized a series of 2-{[2-(4-hydroxyphenyl)ethyl]amino}pyrimidine-5-carboxamide derivatives and evaluated their STAT6 inhibitory activities. Among these compounds, 4-(benzylamino)-2-{[2-(3-chloro-4-hydroxyphenyl)ethyl]amino}pyrimidine-5-carboxamide (2t, AS1517499) showed potent STAT6 inhibition with an IC50 value of 21 nM, and also inhibited IL-4-induced Th2 differentiation of mouse spleen T cells with an IC50 value of 2.3 nM and without influencing T-helper cell 1 (Th1) differentiation induced by IL-12. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.10.015