3-(氨基甲基)-5-氯吡嗪-2-胺 | 1173998-68-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 3-(氨基甲基)-5-氯吡嗪-2-胺
• 英文名称: (2-chloro-5-aminopyrazin-6-yl)methyl amine
• 英文别名: 3-(Aminomethyl)-5-chloropyrazin-2-amine；3-(aminomethyl)-5-chloropyrazin-2-amine
• CAS: 1173998-68-9
• 化学式: C₅H₇ClN₄
• 分子量: 158.59
• InChiKey: YLBRJIYQWLEQBI-UHFFFAOYSA-N

物化性质

• 沸点：
  335.5±37.0 °C(Predicted)
• 密度：
  1.440±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  77.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-氯苯并噻唑 、 3-(氨基甲基)-5-氯吡嗪-2-胺 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以34%的产率得到N-[(3-amino-6-chloropyrazin-2-yl)methyl]-1,3-benzothiazol-2-amine
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of aminopyrazine derivatives as inhibitors of mitogen-activated protein kinase-activated protein kinase 2 (MK-2)

  摘要：

  Several series of novel non-thiourea-containing aminopyrazine derivatives were designed based on the MK-2 inhibitors 1-(2-aminopyrazin-3-yl)methyl-2-thioureas. These compounds were synthesized and evaluated for their inhibitory activity against MK-2 enzyme in vitro. Compounds with low micromolar to sub-micromolar IC50 values were identified, and several compounds were also found to be active in suppressing the lipopolysaccharide (LPS)-stimulated TNF alpha production in THP-1 cells with minimum shift compared to their enzyme activity. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.09.016
• 作为产物：
  描述：

  3-氨基-6-氯-2-氰基吡嗪 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 3-(氨基甲基)-5-氯吡嗪-2-胺
  参考文献：
  名称：

  Novel 1-(2-aminopyrazin-3-yl)methyl-2-thioureas as potent inhibitors of mitogen-activated protein kinase-activated protein kinase 2 (MK-2)

  摘要：

  Novel 1-(2-aminopyrazin-3-yl)methyl-2-thioureas are described as inhibitors of mitogen-activated protein kinase-activated protein kinase 2 (MK-2). These compounds demonstrate potent in vitro activity against the enzyme with IC50 values as low as 15 nM, and suppress expression of TNF alpha in THP-1 cells and in vivo in an acute inflammation model in mice. The synthesis, structure-activity relationship (SAR), and biological evaluation of these compounds are discussed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.088

文献信息

• Design, synthesis, and biological evaluation of aminopyrazine derivatives as inhibitors of mitogen-activated protein kinase-activated protein kinase 2 (MK-2)
  作者：Songnian Lin、Sunita Malkani、Matthew Lombardo、Lihu Yang、Sander G. Mills、Kevin Chapman、James E. Thompson、Wen Xiao Zhang、Ruixiu Wang、Rose M. Cubbon、Edward A. O’Neill、Jeffrey J. Hale

  DOI：10.1016/j.bmcl.2015.09.016

  日期：2015.11

  Several series of novel non-thiourea-containing aminopyrazine derivatives were designed based on the MK-2 inhibitors 1-(2-aminopyrazin-3-yl)methyl-2-thioureas. These compounds were synthesized and evaluated for their inhibitory activity against MK-2 enzyme in vitro. Compounds with low micromolar to sub-micromolar IC50 values were identified, and several compounds were also found to be active in suppressing the lipopolysaccharide (LPS)-stimulated TNF alpha production in THP-1 cells with minimum shift compared to their enzyme activity. (C) 2015 Elsevier Ltd. All rights reserved.
• Novel 1-(2-aminopyrazin-3-yl)methyl-2-thioureas as potent inhibitors of mitogen-activated protein kinase-activated protein kinase 2 (MK-2)
  作者：Songnian Lin、Matthew Lombardo、Sunita Malkani、Jeffrey J. Hale、Sander G. Mills、Kevin Chapman、James E. Thompson、Wen Xiao Zhang、Ruixiu Wang、Rose M. Cubbon、Edward A. O’Neill、Silvi Luell、Ester Carballo-Jane、Lihu Yang

  DOI：10.1016/j.bmcl.2009.04.088

  日期：2009.6

  Novel 1-(2-aminopyrazin-3-yl)methyl-2-thioureas are described as inhibitors of mitogen-activated protein kinase-activated protein kinase 2 (MK-2). These compounds demonstrate potent in vitro activity against the enzyme with IC50 values as low as 15 nM, and suppress expression of TNF alpha in THP-1 cells and in vivo in an acute inflammation model in mice. The synthesis, structure-activity relationship (SAR), and biological evaluation of these compounds are discussed. (C) 2009 Elsevier Ltd. All rights reserved.