2,4-dichloro-6-(3,5-dimethoxyphenylamino)pyrimidine-5-carbonitrile | 725238-05-1

• 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: 2,4-dichloro-6-(3,5-dimethoxyphenylamino)pyrimidine-5-carbonitrile
• 英文别名: 2,4-Dichloro-6-(3,5-dimethoxyanilino)pyrimidine-5-carbonitrile
• CAS: 725238-05-1
• 化学式: C₁₃H₁₀Cl₂N₄O₂
• 分子量: 325.154
• InChiKey: KZLQALOXLOGFSX-UHFFFAOYSA-N

物化性质

• 沸点：
  494.8±45.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  80.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,4-dichloro-6-(3,5-dimethoxyphenylamino)pyrimidine-5-carbonitrile 、 C.I.酸性橙108 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以99%的产率得到4-chloro-6-(3,5-dimethoxyphenylamino)-2-(2-hydroxyethylamino)pyrimidine-5-carbonitrile
  参考文献：
  名称：

  A novel Syk family kinase inhibitor: Design, synthesis, and structure–activity relationship of 1,2,4-triazolo[4,3-c]pyrimidine and 1,2,4-triazolo[1,5-c]pyrimidine derivatives

  摘要：

  Splenic tyrosine kinase (Syk) family kinases, which are members of the protein tyrosine kinase family, play crucial roles in immune responses, with Syk participating in B-cell activation and the zeta-associated protein 70 kDa (ZAP-70) kinase being involved in T-cell activation. Therefore, Syk family kinase inhibitors are candidate therapeutic agents for the treatment of various allergic disorders and autoimmune diseases. We designed 1,2,4-triazolo[4,3-c] pyrimidine and 1,2,4-triazolo[1,5-c] pyrimidine derivatives as Syk family kinase inhibitors, based on literature reports and structure-based drug design. These derivatives showed significant Syk inhibitory activities, with ZAP-70 inhibition. Representative compounds 10d and 11 not only exhibited strong inhibition of both Syk and ZAP-70 kinase but also suppressed IL-2 production by peripheral blood mononuclear cells and whole blood. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.06.017
• 作为产物：
  描述：

  2,4,6-三氯-5-氰基嘧啶 、 3,5-二甲氧基苯胺 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以26%的产率得到2,4-dichloro-6-(3,5-dimethoxyphenylamino)pyrimidine-5-carbonitrile
  参考文献：
  名称：

  A novel Syk family kinase inhibitor: Design, synthesis, and structure–activity relationship of 1,2,4-triazolo[4,3-c]pyrimidine and 1,2,4-triazolo[1,5-c]pyrimidine derivatives

  摘要：

  Splenic tyrosine kinase (Syk) family kinases, which are members of the protein tyrosine kinase family, play crucial roles in immune responses, with Syk participating in B-cell activation and the zeta-associated protein 70 kDa (ZAP-70) kinase being involved in T-cell activation. Therefore, Syk family kinase inhibitors are candidate therapeutic agents for the treatment of various allergic disorders and autoimmune diseases. We designed 1,2,4-triazolo[4,3-c] pyrimidine and 1,2,4-triazolo[1,5-c] pyrimidine derivatives as Syk family kinase inhibitors, based on literature reports and structure-based drug design. These derivatives showed significant Syk inhibitory activities, with ZAP-70 inhibition. Representative compounds 10d and 11 not only exhibited strong inhibition of both Syk and ZAP-70 kinase but also suppressed IL-2 production by peripheral blood mononuclear cells and whole blood. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.06.017