5-(4-octylphenyl)pyrazin-2-aminium chloride | 1353880-07-5

• 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: 5-(4-octylphenyl)pyrazin-2-aminium chloride
• 英文别名: 5-(4-Octylphenyl)pyrazin-2-amine hydrochloride；5-(4-octylphenyl)pyrazin-2-amine;hydrochloride
• CAS: 1353880-07-5
• 化学式: C₁₈H₂₅N₃*ClH
• 分子量: 319.878
• InChiKey: SLLSJVDQFAVSSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.05
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  51.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(4-溴苯基)辛烷 在 2-双环己基膦-2',6'-二甲氧基联苯 、 盐酸 、 正丁基锂 、 palladium diacetate 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙腈 为溶剂， 反应 7.27h， 生成 5-(4-octylphenyl)pyrazin-2-aminium chloride
  参考文献：
  名称：

  Design, synthesis and biological activity of sphingosine kinase 2 selective inhibitors

  摘要：

  Sphingosine kinase (SphK) has emerged as an attractive target for cancer therapeutics due to its role in cell survival. SphK phosphorylates sphingosine to form sphingosine 1-phosphate (S1P), which has been implicated in cancer growth and survival. SphK exists as two different isotypes, namely SphK1 and SphK2, which play different roles inside the cell. In this report, we describe SphK inhibitors based on the immunomodulatory drug, FTY720, which is phosphorylated by SphK2 to generate a S1P mimic. Structural modification of FTY720 provided a template for synthesizing new inhibitors. A diversity-oriented synthesis generated a library of SphK inhibitors with a novel scaffold and headgroup. We have discovered subtype selective inhibitors with K-i's in the low micromolar range. This is the first report describing quaternary ammonium salts as SphK inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.011

文献信息

• Design, synthesis and biological activity of sphingosine kinase 2 selective inhibitors
  作者：Mithun R. Raje、Kenneth Knott、Yugesh Kharel、Philippe Bissel、Kevin R. Lynch、Webster L. Santos

  DOI：10.1016/j.bmc.2011.11.011

  日期：2012.1

  Sphingosine kinase (SphK) has emerged as an attractive target for cancer therapeutics due to its role in cell survival. SphK phosphorylates sphingosine to form sphingosine 1-phosphate (S1P), which has been implicated in cancer growth and survival. SphK exists as two different isotypes, namely SphK1 and SphK2, which play different roles inside the cell. In this report, we describe SphK inhibitors based on the immunomodulatory drug, FTY720, which is phosphorylated by SphK2 to generate a S1P mimic. Structural modification of FTY720 provided a template for synthesizing new inhibitors. A diversity-oriented synthesis generated a library of SphK inhibitors with a novel scaffold and headgroup. We have discovered subtype selective inhibitors with K-i's in the low micromolar range. This is the first report describing quaternary ammonium salts as SphK inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.