2-(2-methyl-5-phenyl-1H-indol-3-yl)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-(2-methyl-5-phenyl-1H-indol-3-yl)ethan-1-amine hydrochloride
• 英文别名: 2-(2-methyl-5-phenyl-1H-indol-3-yl)ethanamine hydrochloride；2-(2-methyl-5-phenyl-1H-indol-3-yl)ethanamine;hydrochloride
• 化学式: C₁₇H₁₈N₂*ClH
• 分子量: 286.804
• InChiKey: XGRIHAVAXOMBRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  41.8
• 氢给体数：
  3
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(2-methyl-5-phenyl-1H-indol-3-yl)ethan-1-amine hydrochloride 在 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.17h， 生成 tert-butyl (2-(1-benzyl-2-methyl-5-phenyl-1H-indol-3-yl)ethyl)carbamate
  参考文献：
  名称：

  Branching tryptamines as a tool to tune their antiproliferative activity

  摘要：

  The influence of a series of tryptamine derivatives on the viability of normal (HEK293) and tumor (HepG2, Jurkat and SH-SY5Y) cells has been evaluated. All tryptamines tested were three different substitution types: C- and N-branching, and indole benzylation. All the derivations enhance the activity of compounds separately, although the effects of different substitutions were not additive. Thus, combinations of C- and N-branchings as well as C-branching and indole benzylation gave little or no increase in activity. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.12.028
• 作为产物：
  描述：

  5-bromo-2-methyltryptamine hydrochloride 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium carbonate 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 6.67h， 生成 2-(2-methyl-5-phenyl-1H-indol-3-yl)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

文献信息

• Branching tryptamines as a tool to tune their antiproliferative activity
  作者：Rinat F. Salikov、Konstantin P. Trainov、Irina K. Belousova、Aleksandr Yu. Belyy、Ulyana Sh. Fatkullina、Regina V. Mulyukova、Liana F. Zainullina、Yulia V. Vakhitova、Yury V. Tomilov

  DOI：10.1016/j.ejmech.2017.12.028

  日期：2018.1

  The influence of a series of tryptamine derivatives on the viability of normal (HEK293) and tumor (HepG2, Jurkat and SH-SY5Y) cells has been evaluated. All tryptamines tested were three different substitution types: C- and N-branching, and indole benzylation. All the derivations enhance the activity of compounds separately, although the effects of different substitutions were not additive. Thus, combinations of C- and N-branchings as well as C-branching and indole benzylation gave little or no increase in activity. (C) 2017 Elsevier Masson SAS. All rights reserved.
• Synthesis and cytotoxic properties of tryptamine derivatives
  作者：Rinat F. Salikov、Aleksandr Yu. Belyy、Nailya S. Khusnutdinova、Yulia V. Vakhitova、Yury V. Tomilov

  DOI：10.1016/j.bmcl.2015.06.070

  日期：2015.9

  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.