2-[(3S,5R)-5-(aminomethyl)-2-benzyl-3-(2-methylpropyl)-1,2-oxazolidin-3-yl]ethanol | 1140535-47-2

• 分子结构分类: 有机化合物
• 英文名称: 2-[(3S,5R)-5-(aminomethyl)-2-benzyl-3-(2-methylpropyl)-1,2-oxazolidin-3-yl]ethanol
• CAS: 1140535-47-2
• 化学式: C₁₇H₂₈N₂O₂
• 分子量: 292.422
• InChiKey: NEZWHFRXSYJUCD-IAGOWNOFSA-N

物化性质

• 沸点：
  418.2±51.0 °C(Predicted)
• 密度：
  1.050±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  58.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [2-[2-(Fmoc-氨基)乙氧基]乙氧基]乙酸 、 2-[(3S,5R)-5-(aminomethyl)-2-benzyl-3-(2-methylpropyl)-1,2-oxazolidin-3-yl]ethanol 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 12.25h， 生成
  参考文献：
  名称：

  Transcriptional Up-regulation in Cells Mediated by a Small Molecule

  摘要：

  Activator artificial transcription factors, molecules that seek out specific genes and up-regulate their transcription, are desirable as mechanistic tools and as potential therapeutic agents. One challenge has been the identification of small molecule-based activator ATFs that function in cellular systems. Here we demonstrate that an amphipathic isoxazolidine activates transcription up to 80-fold in human cells when targeted to a specific promoter. Analogous to natural transcriptional activators, the function of the isoxazolidine appears to be independent of the DNA-targeting moiety, suggesting that the molecule will be effective in a variety of contexts. This is thus a critical step toward activator ATFs constructed from small molecule components.

  DOI：

  10.1021/ja0736865
• 作为产物：
  描述：

  3-(2-benzyl-5-methylazido-3-isobutyl-isoxazolidine-3-yl)-ethanol 在 水 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 2-[(3S,5R)-5-(aminomethyl)-2-benzyl-3-(2-methylpropyl)-1,2-oxazolidin-3-yl]ethanol
  参考文献：
  名称：

  Transcriptional Up-regulation in Cells Mediated by a Small Molecule

  摘要：

  Activator artificial transcription factors, molecules that seek out specific genes and up-regulate their transcription, are desirable as mechanistic tools and as potential therapeutic agents. One challenge has been the identification of small molecule-based activator ATFs that function in cellular systems. Here we demonstrate that an amphipathic isoxazolidine activates transcription up to 80-fold in human cells when targeted to a specific promoter. Analogous to natural transcriptional activators, the function of the isoxazolidine appears to be independent of the DNA-targeting moiety, suggesting that the molecule will be effective in a variety of contexts. This is thus a critical step toward activator ATFs constructed from small molecule components.

  DOI：

  10.1021/ja0736865

文献信息

• Inhibition of ErbB2(Her2) expression with small molecule transcription factor mimics
  作者：Lori W. Lee、Christopher E.C. Taylor、Jean-Paul Desaulniers、Manchao Zhang、Jonas W. Højfeldt、Quintin Pan、Anna K. Mapp

  DOI：10.1016/j.bmcl.2009.08.090

  日期：2009.11

  Small molecules that mimic the transcriptional activation domain of eukaryotic transcriptional activators have the potential to serve as effective inhibitors of transcriptional processes. Here we show that one class of transcriptional activation domain mimics, amphipathic isoxazolidines, can be converted into inhibitors of gene expression mediated by the transcriptional activator ESX through small structural modi. cations. Addition of the small molecules leads to decreased expression of the cell surface growth receptor ErbB2(Her2) in ErbB2-positive cancer cells and, correspondingly, decreased proliferation. (C) 2009 Elsevier Ltd. All rights reserved.