N-(12-amino-4,9-diazadodec-1-yl)-1H-indole-3-acetamide

• 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-(12-amino-4,9-diazadodec-1-yl)-1H-indole-3-acetamide
• 英文别名: N¹-spermine 2-(3-indolyl)acetamide；N-[3-[4-(3-aminopropylamino)butylamino]propyl]-2-(1H-indol-3-yl)acetamide
• 化学式: C₂₀H₃₃N₅O
• 分子量: 359.515
• InChiKey: CTOQMXFECNSQIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  26
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  95
• 氢给体数：
  5
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-吲哚乙酸 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 23.0h， 生成 N-(12-amino-4,9-diazadodec-1-yl)-1H-indole-3-acetamide
  参考文献：
  名称：

  Characterization and synthesis of a new calcium antagonist from the venom of a fishing spider

  摘要：

  A new calcium antagonist, CNS 2103, is isolated from the venom of a fishing spider, Dolomedes okefinokensis. The structure of this compound is derived from spectroscopic data, including tandem mass spectrometry. A flexible, convergent synthesis of CNS 2103 is described.

  DOI：

  10.1016/s0040-4020(01)81803-2

文献信息

• Fukuyama–Mitsunobu alkylation in amine synthesis on solid phase revisited: N-alkylation with secondary alcohols and synthesis of curtatoxins
  作者：Christian A. Olsen、Matthias Witt、Steen H. Hansen、Jerzy W. Jaroszewski、Henrik Franzyk

  DOI：10.1016/j.tet.2005.04.027

  日期：2005.6

  sulfonamides, as well as a method for synthesis of polyamines on solid phase. Here, an array of reagent combinations for solid-phase alkylation with secondary alcohols was examined in various solvents. The classical reagents DEAD–PPh3 as well as DEAD–PEt3 proved applicable for a single alkylation step. Sharply dropping yields in successive alkylation steps were identified as the most serious limitation of the

  Fukuyama–Mitsunobu胺化策略已成为肽和磺酰胺N-烷基化的有效手段，以及固相合成多胺的方法。在此，在各种溶剂中检查了一系列与仲醇固相烷基化的试剂组合。经典试剂DEAD–PPh 3和DEAD–PEt 3被证明可用于单个烷基化步骤。连续烷基化步骤中收率的急剧下降被认为是使用伯醇，尤其是仲醇在多胺SPS中使用福山-光延反应的最严重限制。
• Amino Acid/Spermine Conjugates:  Polyamine Amides as Potent Spermidine Uptake Inhibitors
  作者：Mark R. Burns、C. Lance Carlson、Scott M. Vanderwerf、Josh R. Ziemer、Reitha S. Weeks、Feng Cai、Heather K. Webb、Gerard F. Graminski

  DOI：10.1021/jm0101040

  日期：2001.10.1

  In this paper we describe the synthesis and characterization of a series of simple spermine/amino acid conjugates, some of which potently inhibit the uptake of spermidine into MDAMB-231 breast cancer cells. The presence of an amide in the functionalized polyamine appeared to add to the affinity for the polyamine transporter. The extensive biological characterization of an especially potent analogue from this series, the Lys-Spm conjugate (31), showed this molecule will be an extremely useful tool for use in polyamine research. It was shown that the use of 31 in combination with DFMO led to a cytostatic growth inhibition of a variety of cancer cells, even when used in the presence of an extracellular source of transportable spermidine. It was furthermore shown that this combination effectively reduced the cellular levels of putrescine and spermidine while not affecting the levels of spermine. These facts together with the nontoxic nature of 31 make it a novel lead for further anticancer development.
• JPH02256656A
  申请人：——

  公开号：JPH02256656A

  公开（公告）日：1990-10-17