N(1)-(6-chloropyrazin-2-yl)ethane-1,2-diamine | 1138220-48-0

• 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: N(1)-(6-chloropyrazin-2-yl)ethane-1,2-diamine
• 英文别名: N-(2-aminoethyl)-6-chloropyrazin-2-amine；N'-(6-chloropyrazin-2-yl)ethane-1,2-diamine
• CAS: 1138220-48-0
• 化学式: C₆H₉ClN₄
• mdl: MFCD20687264
• 分子量: 172.617
• InChiKey: DJXKSIOYNWWXAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  63.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N(1)-(6-chloropyrazin-2-yl)ethane-1,2-diamine 、 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 0.17h， 生成
  参考文献：
  名称：

  Discovery and evaluation of 3,5-disubstituted indole derivatives as Pim kinase inhibitors

  摘要：

  Pim kinases are promising therapeutic targets for the treatment of hematological cancers. A potent Pim kinase inhibitor 7f, derived from meridianin C, was further optimized by the replacement of 2-aminopyrimidine with substituted benzene. The optimization of the C-3 and C-5 positions of indole yielded compound 43 with improved cellular potency and high selectivity against a panel of 14 different kinases.

  DOI：

  10.1016/j.bmcl.2018.05.054
• 作为产物：
  描述：

  2,6-二氯吡嗪 、 乙二胺 以 二氯甲烷 为溶剂， 生成 N(1)-(6-chloropyrazin-2-yl)ethane-1,2-diamine
  参考文献：
  名称：

  Hit to Lead Account of the Discovery of a New Class of Inhibitors of Pim Kinases and Crystallographic Studies Revealing an Unusual Kinase Binding Mode

  摘要：

  A series of inhibitors of Pim-2 kinase identified by high-throughput screening is described. Details of the hit validation and lead generation process and structure-activity relationship (SAR) studies are presented. Disclosure of an unconventional binding mode for 1, as revealed by X-ray crystallography using the highly homologous Pim-1 protein, is also presented, and observed binding features are shown to correlate with the Pim-2 SAR. While highly selective within the kinase family, the series shows similar potency for both Pim-1 and Pim-2, which was expected on the basis of homology, but unusual in light of reports in the literature documenting a bias for Pim-1. A rationale for these observations based on Pim-1 and Pim-2 K(M(ATP)) values is suggested. Some interesting cross reactivity with casein kinase-2 was also identified, and structural features which may contribute to the association are discussed.

  DOI：

  10.1021/jm801242y