2-(5-bromo-2-methyl-1H-indol-3-yl)-N-((7-methoxybenzo[d][1,3]dioxol-5-yl)methyl)ethan-1-amine hydrochloride

• 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: 2-(5-bromo-2-methyl-1H-indol-3-yl)-N-((7-methoxybenzo[d][1,3]dioxol-5-yl)methyl)ethan-1-amine hydrochloride
• 英文别名: 2-(5-bromo-2-methyl-1H-indol-3-yl)-N-[(7-methoxy-1,3-benzodioxol-5-yl)methyl]ethanamine;hydrochloride
• 化学式: C₂₀H₂₁BrN₂O₃*ClH
• 分子量: 453.763
• InChiKey: AVBOGTVRGGQCKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.73
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.5
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-bromo-2-methyltryptamine hydrochloride 、 肉豆蔻醛 在 sodium acetate 、 sodium cyanoborohydride 、 溶剂黄146 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 24.0h， 以60%的产率得到2-(5-bromo-2-methyl-1H-indol-3-yl)-N-((7-methoxybenzo[d][1,3]dioxol-5-yl)methyl)ethan-1-amine hydrochloride
  参考文献：
  名称：

  Synthesis and cytotoxic properties of tryptamine derivatives

  摘要：

  The cyclopropyliminium and subsequent Grandberg rearrangements of cyclopropylketone hydrozones lead to the formation of tryptamines, which were additionally substituted at either the aromatic ring atoms or the amino group. The products were tested for their cytotoxic properties against HepG2, Jurkat and HEK293 cell lines using MTT assay. The highest activity as well as the highest selectivity was found amongst the compounds derived with one benzyl substituent at the amino group. The flow cytometry technique revealed cell-type specificity in terms of the mechanism of viability inhibition. Thus, the compounds were found to induce mainly apoptosis in HEK293 and HepG2 cells, while Jurkat cells displayed late apoptotic and necrotic responses. The apoptosis pathway is most likely to include mitochondrial damage. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.06.070