N,N-Dibenzyl-4,6,7-trimethoxytryptamine

• 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: N,N-Dibenzyl-4,6,7-trimethoxytryptamine
• 英文别名: N,N-dibenzyl-2-(4,6,7-trimethoxy-1H-indol-3-yl)ethanamine
• 化学式: C₂₇H₃₀N₂O₃
• 分子量: 430.547
• InChiKey: SFLJWMUSNWRAKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  46.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-甲苯磺酸酐 、 N,N-Dibenzyl-4,6,7-trimethoxytryptamine 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以98%的产率得到1-(p-Toluenesulfonyl)-4,6,7-trimethoxy-N,N-dibenzyltryptamine
  参考文献：
  名称：

  Efficient Syntheses of the Marine Alkaloids Makaluvamine D and Discorhabdin C: The 4,6,7-Trimethoxyindole Approach

  摘要：

  A new and efficient synthesis of the tricyclic quinonimine 20 as its trifluoroacetate 23 has been developed starting from the commercially available 2,4,5-trimethoxybenzaldehyde and proceeding via the hitherto unknown 4,6,7-trimethoxyindole (7). Quinonimine 23 is the late stage key intermediate in several previously reported syntheses of the biologically active pyrrolo[4,3,2-de]-quinoline marine alkaloids discorhabdin C (1) and makaluvamine D (3).

  DOI：

  10.1021/jo00111a043
• 作为产物：
  描述：

  N,N-Dibenzyl-4,6,7-trimethoxyindole-3-glyoxylamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 8.0h， 以98%的产率得到N,N-Dibenzyl-4,6,7-trimethoxytryptamine
  参考文献：
  名称：

  Efficient Syntheses of the Marine Alkaloids Makaluvamine D and Discorhabdin C: The 4,6,7-Trimethoxyindole Approach

  摘要：

  A new and efficient synthesis of the tricyclic quinonimine 20 as its trifluoroacetate 23 has been developed starting from the commercially available 2,4,5-trimethoxybenzaldehyde and proceeding via the hitherto unknown 4,6,7-trimethoxyindole (7). Quinonimine 23 is the late stage key intermediate in several previously reported syntheses of the biologically active pyrrolo[4,3,2-de]-quinoline marine alkaloids discorhabdin C (1) and makaluvamine D (3).

  DOI：

  10.1021/jo00111a043

文献信息

• Marine Alkalod Makaluvamines and Derivatives Thereof
  申请人：Velu Sadanandan E.

  公开号：US20100144779A1

  公开（公告）日：2010-06-10

  The present disclosure provides compounds based on the marine alkaloid makaluvamine. Described are compounds of the general formula (I) and (II). Also described are pharmaceutical compositions comprising one or more of the compounds of the general formula (I) and (II). The compounds and pharmaceutical compositions described inhibit the growth of several cancer lines, induce apoptosis and cell cycle arrest, display topoisomerase II inhibitory activity and modulate the activity and/or expression of key proteins involved in the regulation of cell growth. Methods of treatment and prevention using the compounds and pharmaceutical compositions described are also provided.
• Efficient Syntheses of the Marine Alkaloids Makaluvamine D and Discorhabdin C: The 4,6,7-Trimethoxyindole Approach
  作者：Eyyani V. Sadanandan、Sasi K. Pillai、M. V. Lakshmikantham、Adil D. Billimoria、J. Shane Culpepper、Michael P. Cava

  DOI：10.1021/jo00111a043

  日期：1995.3

  A new and efficient synthesis of the tricyclic quinonimine 20 as its trifluoroacetate 23 has been developed starting from the commercially available 2,4,5-trimethoxybenzaldehyde and proceeding via the hitherto unknown 4,6,7-trimethoxyindole (7). Quinonimine 23 is the late stage key intermediate in several previously reported syntheses of the biologically active pyrrolo[4,3,2-de]-quinoline marine alkaloids discorhabdin C (1) and makaluvamine D (3).