(1S,3S)-1-(3-nitrophenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid | 869304-07-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: (1S,3S)-1-(3-nitrophenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid
• 英文别名: (1S,3S)-1-(3-nitrophenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-2-ium-3-carboxylate
• CAS: 869304-07-4
• 化学式: C₁₈H₁₅N₃O₄
• 分子量: 337.335
• InChiKey: CYXGKHWORVZUGJ-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  111
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,3S)-1-(3-nitrophenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid 、 异氰酸乙酯 以 二甲基亚砜 、 丙酮 为溶剂， 以21%的产率得到(5S,11aS)-2-ethyl-5-(3-nitrophenyl)-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：

  间硝基苯甲醛 、 L-色氨酸 在 硫酸 作用下， 以71%的产率得到(1S,3S)-1-(3-nitrophenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid
  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

文献信息

• Synthesis and biological evaluation of new tetrahydro-β-carbolines as inhibitors of the mitotic kinesin Eg5
  作者：Nils Sunder-Plassmann、Vasiliki Sarli、Michael Gartner、Mathias Utz、Jeanette Seiler、Stefan Huemmer、Thomas U. Mayer、Thomas Surrey、Athanassios Giannis

  DOI：10.1016/j.bmc.2005.06.027

  日期：2005.11

  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.