1-bromo-9-(3-phenylpropyl)-β-carboline | 1160060-58-1

• 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: 1-bromo-9-(3-phenylpropyl)-β-carboline
• 英文别名: 1-Bromo-9-(3-phenylpropyl)pyrido[3,4-b]indole
• CAS: 1160060-58-1
• 化学式: C₂₀H₁₇BrN₂
• 分子量: 365.272
• InChiKey: STBJZGKVJURWPW-UHFFFAOYSA-N

物化性质

• 熔点：
  113-114 °C
• 沸点：
  536.6±50.0 °C(predicted)
• 密度：
  1.36±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-bromo-9-(3-phenylpropyl)-β-carboline 、 四亚甲基二胺 在 copper(l) iodide 作用下， 反应 0.5h， 以71%的产率得到1-(4-aminobutylamino)-9-(3-phenylpropyl)-β-carboline
  参考文献：
  名称：

  Synthesis and cytotoxic evaluation of 1-carboxamide and 1-amino side chain substituted β-carbolines

  摘要：

  The condensation of alkylenediamine with ethyl beta-carboline-1-carboxylate and 1-bromo-beta-carboline gave beta-carboline-1-carboxamides and 1-amino-beta-carbolines, respectively. Some of these beta-carbolines were active against a panel of human tumor cell lines, and 1-amino derivatives were more potent than their 1-carboxamide congeners. In particular, among the 1-amino-beta-carbolines, the N-9-arylated alkyl substituted beta-carbolines exhibited the most interesting cytotoxic activities with IC50 value of lower than 20 mu M. The preliminary structure activity relationships (SARs) analysis suggested that (1) 1-amino substituents were the advisable pharmacophoric group for enhanced cytotoxic activities; (2) the introduction of appropriate arylated alkyl groups into position-9 of beta-carboline facilitated their cytotoxic potencies. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.08.065
• 作为产物：
  描述：

  1-溴-3-苯基丙烷 、 1-溴-9h-吡啶并[3,4-b]吲哚 在 potassium iodide 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 2.25h， 以93%的产率得到1-bromo-9-(3-phenylpropyl)-β-carboline
  参考文献：
  名称：

  Synthesis and cytotoxic evaluation of 1-carboxamide and 1-amino side chain substituted β-carbolines

  摘要：

  The condensation of alkylenediamine with ethyl beta-carboline-1-carboxylate and 1-bromo-beta-carboline gave beta-carboline-1-carboxamides and 1-amino-beta-carbolines, respectively. Some of these beta-carbolines were active against a panel of human tumor cell lines, and 1-amino derivatives were more potent than their 1-carboxamide congeners. In particular, among the 1-amino-beta-carbolines, the N-9-arylated alkyl substituted beta-carbolines exhibited the most interesting cytotoxic activities with IC50 value of lower than 20 mu M. The preliminary structure activity relationships (SARs) analysis suggested that (1) 1-amino substituents were the advisable pharmacophoric group for enhanced cytotoxic activities; (2) the introduction of appropriate arylated alkyl groups into position-9 of beta-carboline facilitated their cytotoxic potencies. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.08.065

文献信息

• Synthesis and cytotoxic evaluation of 1-carboxamide and 1-amino side chain substituted β-carbolines
  作者：Chunming Ma、Rihui Cao、Buxi Shi、Xiantai Zhou、Qin Ma、Jie Sun、Liang Guo、Wei Yi、Zhiyong Chen、Huacan Song

  DOI：10.1016/j.ejmech.2010.08.065

  日期：2010.11

  The condensation of alkylenediamine with ethyl beta-carboline-1-carboxylate and 1-bromo-beta-carboline gave beta-carboline-1-carboxamides and 1-amino-beta-carbolines, respectively. Some of these beta-carbolines were active against a panel of human tumor cell lines, and 1-amino derivatives were more potent than their 1-carboxamide congeners. In particular, among the 1-amino-beta-carbolines, the N-9-arylated alkyl substituted beta-carbolines exhibited the most interesting cytotoxic activities with IC50 value of lower than 20 mu M. The preliminary structure activity relationships (SARs) analysis suggested that (1) 1-amino substituents were the advisable pharmacophoric group for enhanced cytotoxic activities; (2) the introduction of appropriate arylated alkyl groups into position-9 of beta-carboline facilitated their cytotoxic potencies. (C) 2010 Elsevier Masson SAS. All rights reserved.