5-(N-benzylmethylamino)-7-(3,5-dimethoxyphenylamino)imidazo[1,2-c]pyrimidine-8-carboxamide | 725235-54-1

• 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: 5-(N-benzylmethylamino)-7-(3,5-dimethoxyphenylamino)imidazo[1,2-c]pyrimidine-8-carboxamide
• 英文别名: Imidazo[1,2-c]pyrimidine-8-carboxamide, 10e；5-[benzyl(methyl)amino]-7-(3,5-dimethoxyanilino)imidazo[1,2-c]pyrimidine-8-carboxamide
• CAS: 725235-54-1
• 化学式: C₂₃H₂₄N₆O₃
• 分子量: 432.482
• InChiKey: WRTLOLDYSMFKTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  7-(3,5-dimethoxy-phenylamino)-5-methylsulfanyl-imidazo[1,2-c]pyrimidine-8-carboxylic acid amide 、 N-甲基苄胺 以 N-甲基吡咯烷酮 为溶剂， 反应 3.0h， 以38%的产率得到5-(N-benzylmethylamino)-7-(3,5-dimethoxyphenylamino)imidazo[1,2-c]pyrimidine-8-carboxamide
  参考文献：
  名称：

  Structure–activity relationship studies of 5-benzylaminoimidazo[1,2-c]pyrimidine-8-carboxamide derivatives as potent, highly selective ZAP-70 kinase inhibitors

  摘要：

  Zeta-associated protein, 70 kDa (ZAP-70), a spleen tyrosine kinase (Syk) family kinase, is normally expressed on T cells and natural killer cells and plays a crucial role in activation of the T cell immunoresponse. Thus, selective ZAP-70 inhibitors might be useful not only for treating autoimmune diseases, but also for suppressing organ transplant rejection. In our recent study on the synthesis of Syk family kinase inhibitors, we discovered that novelimidazo[1,2-c]pyrimidine-8-carboxamide derivatives possessed potent ZAP-70 inhibitory activity with good selectivity for ZAP-70 over other kinases. In particular, compound 26 showed excellent ZAP-70 kinase inhibition and high selectivity for ZAP-70 over structurally related Syk. The discovery of a potent, highly selective ZAP-70 inhibitor would contribute a new therapeutic tool for autoimmune diseases and organ transplant medication. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.070

文献信息

• Structure–activity relationship studies of 5-benzylaminoimidazo[1,2-c]pyrimidine-8-carboxamide derivatives as potent, highly selective ZAP-70 kinase inhibitors
  作者：Akihito Hirabayashi、Harunobu Mukaiyama、Hiroaki Kobayashi、Hiroaki Shiohara、Satoko Nakayama、Motoyasu Ozawa、Keiji Miyazawa、Keiko Misawa、Hideki Ohnota、Masayuki Isaji

  DOI：10.1016/j.bmc.2008.10.070

  日期：2009.1

  Zeta-associated protein, 70 kDa (ZAP-70), a spleen tyrosine kinase (Syk) family kinase, is normally expressed on T cells and natural killer cells and plays a crucial role in activation of the T cell immunoresponse. Thus, selective ZAP-70 inhibitors might be useful not only for treating autoimmune diseases, but also for suppressing organ transplant rejection. In our recent study on the synthesis of Syk family kinase inhibitors, we discovered that novelimidazo[1,2-c]pyrimidine-8-carboxamide derivatives possessed potent ZAP-70 inhibitory activity with good selectivity for ZAP-70 over other kinases. In particular, compound 26 showed excellent ZAP-70 kinase inhibition and high selectivity for ZAP-70 over structurally related Syk. The discovery of a potent, highly selective ZAP-70 inhibitor would contribute a new therapeutic tool for autoimmune diseases and organ transplant medication. (C) 2008 Elsevier Ltd. All rights reserved.