(5S,11aS)-5-(3-hydroxyphenyl)-2-pentyl-6H-1,2,3,5,11,11a-hexahydro-imidazo[1,5-b]-β-carboline-1,3-dione | 869304-27-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (5S,11aS)-5-(3-hydroxyphenyl)-2-pentyl-6H-1,2,3,5,11,11a-hexahydro-imidazo[1,5-b]-β-carboline-1,3-dione
• CAS: 869304-27-8
• 化学式: C₂₄H₂₅N₃O₃
• 分子量: 403.481
• InChiKey: MGSXYDYENTZVSO-UNMCSNQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.34
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  76.64
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (5S,11aS)-5-(3-hydroxyphenyl)-2-pentyl-6H-1,2,3,5,11,11a-hexahydro-imidazo[1,5-b]-β-carboline-1,3-dione 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以93%的产率得到(5S,11aR)-5-(3-hydroxyphenyl)-2-pentyl-6H-1,2,3,5,11,11a-hexahydro-imidazo[1,5-b]-β-carboline-1,3-dione
  参考文献：
  名称：

  Synthesis and biological evaluation of new tetrahydro-β-carbolines as inhibitors of the mitotic kinesin Eg5

  摘要：

  The mitotic kinesin Eg5 (or KSP) is a crucial player in the development and function of the mitotic spindle. Inhibition of this protein leads to cell cycle arrest and apoptosis without interfering with other microtubule-dependent processes. Therefore, it is a potential target in cancer therapy. Here, we report the synthesis and biological evaluation of a small library of molecules based on the structure of the known Eg5 inhibitor HR22C16. One of these derivatives (compound trans-24) proved to be a potent and specific Eg5 inhibitor. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.06.027
• 作为产物：
  描述：

  L-色氨酸 在 硫酸 作用下， 以 二甲基亚砜 、 丙酮 为溶剂， 生成 (5S,11aS)-5-(3-hydroxyphenyl)-2-pentyl-6H-1,2,3,5,11,11a-hexahydro-imidazo[1,5-b]-β-carboline-1,3-dione
  参考文献：
  名称：

  Synthesis and biological evaluation of new tetrahydro-β-carbolines as inhibitors of the mitotic kinesin Eg5

  摘要：

  The mitotic kinesin Eg5 (or KSP) is a crucial player in the development and function of the mitotic spindle. Inhibition of this protein leads to cell cycle arrest and apoptosis without interfering with other microtubule-dependent processes. Therefore, it is a potential target in cancer therapy. Here, we report the synthesis and biological evaluation of a small library of molecules based on the structure of the known Eg5 inhibitor HR22C16. One of these derivatives (compound trans-24) proved to be a potent and specific Eg5 inhibitor. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.06.027