4-(6-(4-octylphenyl)pyridin-2-yl)piperazin-1-ium chloride | 1353880-08-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 4-(6-(4-octylphenyl)pyridin-2-yl)piperazin-1-ium chloride
• 英文别名: 1-(6-(4-Octylphenyl)pyridin-2-yl)piperazine hydrochloride；1-[6-(4-octylphenyl)pyridin-2-yl]piperazine;hydrochloride
• CAS: 1353880-08-6
• 化学式: C₂₃H₃₃N₃*ClH
• 分子量: 387.996
• InChiKey: YKCOQSWGYSWRFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.48
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  28.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  tert-butyl 4-(6-(4-octylphenyl)pyridin-2-yl)piperazine-1-carboxylate 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 0.02h， 以92%的产率得到4-(6-(4-octylphenyl)pyridin-2-yl)piperazin-1-ium 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.