2-[(4-Morpholin-4-ylphenyl)amino]-4-[(2-nitrobenzyl)amino]pyrimidine-5-carboxamide | 643083-10-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 2-[(4-Morpholin-4-ylphenyl)amino]-4-[(2-nitrobenzyl)amino]pyrimidine-5-carboxamide
• 英文别名: 2-(4-morpholin-4-ylanilino)-4-[(2-nitrophenyl)methylamino]pyrimidine-5-carboxamide
• CAS: 643083-10-7
• 化学式: C₂₂H₂₃N₇O₄
• 分子量: 449.469
• InChiKey: JCDSUHIIORPINC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  151
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-[(4-Morpholin-4-ylphenyl)amino]-4-[(2-nitrobenzyl)amino]pyrimidine-5-carboxamide 在 palladium on activated charcoal 氢气 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以63%的产率得到4-(2-aminobenzyl)amino-2-{[4-(morpholin-4-yl)phenyl]amino}pyrimidine-5-carboxamide
  参考文献：
  名称：

  Identification of 4-benzylamino-2-[(4-morpholin-4-ylphenyl)amino]pyrimidine-5-carboxamide derivatives as potent and orally bioavailable STAT6 inhibitors

  摘要：

  Signal transducers and activators of transcription 6 (STAT6) is a key regulator of the type 2 helper T (Th2) cell immune response and a potential therapeutic target for allergic diseases such as asthma and atopic diseases. To search for potent and orally bioavailable STAT6 inhibitors, we synthesized a series of 4-benzylaminopyrimidine-5- carboxamide derivatives and evaluated their STAT6 inhibitory activities. Among these compounds, 2-[(4-morpholin-4-ylphenyl)amino]-4-[(2,3,6- trifluorobenzyl)amino]pyrimidine-5-carboxamide (25y, YM-341619, AS1617612) showed potent STAT6 inhibition with an IC(50) of 0.70 nM, and also inhibited Th2 differentiation in mouse spleen T cells induced by interleukin (IL)-4 with an IC(50) of 0.28 nM without affecting type 1 helper T (Th1) cell differentiation induced by IL-12. In addition, compound 25y showed an oral bioavailability of 25% in mouse. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.05.031
• 作为产物：
  描述：

  4-(4-吗啉基)苯胺 、 2-chloro-4-[(2-nitrobenzyl)amino]pyrimidine-5-carboxamide 在 dioxanic HCl 作用下， 以 N-甲基吡咯烷酮 为溶剂， 生成 2-[(4-Morpholin-4-ylphenyl)amino]-4-[(2-nitrobenzyl)amino]pyrimidine-5-carboxamide
  参考文献：
  名称：

  Identification of 4-benzylamino-2-[(4-morpholin-4-ylphenyl)amino]pyrimidine-5-carboxamide derivatives as potent and orally bioavailable STAT6 inhibitors

  摘要：

  Signal transducers and activators of transcription 6 (STAT6) is a key regulator of the type 2 helper T (Th2) cell immune response and a potential therapeutic target for allergic diseases such as asthma and atopic diseases. To search for potent and orally bioavailable STAT6 inhibitors, we synthesized a series of 4-benzylaminopyrimidine-5- carboxamide derivatives and evaluated their STAT6 inhibitory activities. Among these compounds, 2-[(4-morpholin-4-ylphenyl)amino]-4-[(2,3,6- trifluorobenzyl)amino]pyrimidine-5-carboxamide (25y, YM-341619, AS1617612) showed potent STAT6 inhibition with an IC(50) of 0.70 nM, and also inhibited Th2 differentiation in mouse spleen T cells induced by interleukin (IL)-4 with an IC(50) of 0.28 nM without affecting type 1 helper T (Th1) cell differentiation induced by IL-12. In addition, compound 25y showed an oral bioavailability of 25% in mouse. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.05.031