N-[3-(4-indolyloxy)-2-hydroxypropyl]-N'-Boc-1,3-propanediamine | 674774-61-9

• 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-[3-(4-indolyloxy)-2-hydroxypropyl]-N'-Boc-1,3-propanediamine
• CAS: 674774-61-9
• 化学式: C₁₉H₂₉N₃O₄
• 分子量: 363.457
• InChiKey: UJFYIKHBXASKBX-UHFFFAOYSA-N

物化性质

• 沸点：
  585.2±50.0 °C(Predicted)
• 密度：
  1.172±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 重原子数：
  26.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  95.61
• 氢给体数：
  4.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-[3-(4-indolyloxy)-2-hydroxypropyl]-N'-Boc-1,3-propanediamine 、 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 30.0h， 以250 mg的产率得到tert-butyl N-[3-[[4-[1-(adamantane-1-carbonyl)piperidin-4-yl]piperidine-1-carbonyl]-[2-hydroxy-3-(1H-indol-4-yloxy)propyl]amino]propyl]carbamate
  参考文献：
  名称：

  A Wrench-Shaped Synthetic Molecule that Modulates a Transcription Factor−Coactivator Interaction

  摘要：

  Development of synthetic molecules that provide external control over the transcription of a given gene represents a challenge in medicinal and bioorganic chemistry. Here we report design and analysis of wrenchnolol, a wrench-shaped synthetic molecule that impairs the transcription of the Her2 oncogene by disrupting association of transcription factor ESX with its coactivator Sur-2. The "jaw" part of the compound mimics the alpha-helical interface of the activation domain of ESX, and the "handle" region accepts chemical modifications for a range of analysis. A water-soluble handle permitted NMR study in aqueous solution; a biotinylated handle verified the selectivity of the interaction, and a fluorescent handle confirmed the cell permeability of the compound. The case study of wrenchnolol foreshadows the promise and the challenge of targeting protein-protein interactions in the nucleus and may lead to the development of unique synthetic modulators of gene transcription.

  DOI：

  10.1021/ja038855+
• 作为产物：
  描述：

  4-羟基吲哚 在 氢氧化钾 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 36.0h， 生成 N-[3-(4-indolyloxy)-2-hydroxypropyl]-N'-Boc-1,3-propanediamine
  参考文献：
  名称：

  A Wrench-Shaped Synthetic Molecule that Modulates a Transcription Factor−Coactivator Interaction

  摘要：

  Development of synthetic molecules that provide external control over the transcription of a given gene represents a challenge in medicinal and bioorganic chemistry. Here we report design and analysis of wrenchnolol, a wrench-shaped synthetic molecule that impairs the transcription of the Her2 oncogene by disrupting association of transcription factor ESX with its coactivator Sur-2. The "jaw" part of the compound mimics the alpha-helical interface of the activation domain of ESX, and the "handle" region accepts chemical modifications for a range of analysis. A water-soluble handle permitted NMR study in aqueous solution; a biotinylated handle verified the selectivity of the interaction, and a fluorescent handle confirmed the cell permeability of the compound. The case study of wrenchnolol foreshadows the promise and the challenge of targeting protein-protein interactions in the nucleus and may lead to the development of unique synthetic modulators of gene transcription.

  DOI：

  10.1021/ja038855+