N-[3-(N-tosyl-4-indolyloxy)-2-hydroxypropyl]-N'-Boc-1,3-propanediamine | 674774-62-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[3-(N-tosyl-4-indolyloxy)-2-hydroxypropyl]-N'-Boc-1,3-propanediamine
• 英文别名: tert-butyl N-[3-[[2-hydroxy-3-[1-(4-methylphenyl)sulfonylindol-4-yl]oxypropyl]amino]propyl]carbamate
• CAS: 674774-62-0
• 化学式: C₂₆H₃₅N₃O₆S
• 分子量: 517.646
• InChiKey: ZAPIYSGNPQGCNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  127
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-[3-(N-tosyl-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353 mg的产率得到[3-([1'-(Adamantane-1-carbonyl)-[4,4']bipiperidinyl-1-carbonyl]-{2-hydroxy-3-[1-(toluene-4-sulfonyl)-1H-indol-4-yloxy]-propyl}-amino)-propyl]-carbamic acid tert-butyl ester
  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-(2,3-环氧丙氧基)吲哚 在 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 32.0h， 生成 N-[3-(N-tosyl-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+

文献信息

• Small molecule inhibitors of HER2 expression
  申请人：Uesugi Motonari

  公开号：US20050283007A1

  公开（公告）日：2005-12-22

  Peptide mimetic small molecule inhibitors of Sur-2 are provided having the general formula:

  提供了具有一般公式的Sur-2肽类模拟小分子抑制剂：
• US7449480B2
  申请人：——

  公开号：US7449480B2

  公开（公告）日：2008-11-11