[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 | 674774-66-4

• 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: [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
• CAS: 674774-66-4
• 化学式: C₄₈H₆₇N₅O₈S
• 分子量: 874.155
• InChiKey: RAMCNJUPADDOSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.43
• 重原子数：
  62.0
• 可旋转键数：
  13.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  150.72
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  三氟乙酸 、 [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 以 氯仿 为溶剂， 反应 0.25h， 以100%的产率得到1'-(Adamantane-1-carbonyl)-[4,4']bipiperidinyl-1-carboxylic acid (3-amino-propyl)-{2-hydroxy-3-[1-(toluene-4-sulfonyl)-1H-indol-4-yloxy]-propyl}-amide; compound with trifluoro-acetic acid
  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：

  金刚烷酰氯 在 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 乙腈 为溶剂， 反应 52.5h， 生成 [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+