2-[1-[2-[2-(2-Hydroxyethoxy)ethoxy]ethyl]indol-3-yl]acetamide | 436867-46-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-[1-[2-[2-(2-Hydroxyethoxy)ethoxy]ethyl]indol-3-yl]acetamide
• CAS: 436867-46-8
• 化学式: C₁₆H₂₂N₂O₄
• 分子量: 306.362
• InChiKey: MQOQDDZUSSXLEZ-UHFFFAOYSA-N

物化性质

• 沸点：
  582.1±50.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  86.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[1-[2-[2-(2-Hydroxyethoxy)ethoxy]ethyl]indol-3-yl]acetamide 在 吡啶 、 盐酸 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 生成 Methanesulfonic acid 3-{3-[4-(1-{2-[2-(2-methanesulfonyloxy-ethoxy)-ethoxy]-ethyl}-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-indol-1-yl}-propyl ester
  参考文献：
  名称：

  Macrocyclic bisindolylmaleimides as inhibitors of protein kinase C and glycogen synthase kinase-3

  摘要：

  Efficient methods were developed to synthesize a novel series of macrocyclic bisindolylmaleimides containing linkers with multiple heteroatoms. Potent inhibitors (single digit nanomolar IC50) for PKC-beta and GSK-3beta were identified, and compounds showed good selectivity over PKC-alpha, -gamma, delta, -epsilon, and -zeta. Representative compound 5a also had high selectivity in a screening panel of 10 other protein kinases. In cell-based functional assays, several compounds effectively blocked interleukin-8 release induced by PKC-beta11 and increased glycogen synthase activity by inhibiting GSK-3beta. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00644-9
• 作为产物：
  描述：

  3-吲哚乙酰胺 、 2-氯乙氧基-2-乙氧基二乙醇 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以82%的产率得到2-[1-[2-[2-(2-Hydroxyethoxy)ethoxy]ethyl]indol-3-yl]acetamide
  参考文献：
  名称：

  Macrocyclic bisindolylmaleimides as inhibitors of protein kinase C and glycogen synthase kinase-3

  摘要：

  Efficient methods were developed to synthesize a novel series of macrocyclic bisindolylmaleimides containing linkers with multiple heteroatoms. Potent inhibitors (single digit nanomolar IC50) for PKC-beta and GSK-3beta were identified, and compounds showed good selectivity over PKC-alpha, -gamma, delta, -epsilon, and -zeta. Representative compound 5a also had high selectivity in a screening panel of 10 other protein kinases. In cell-based functional assays, several compounds effectively blocked interleukin-8 release induced by PKC-beta11 and increased glycogen synthase activity by inhibiting GSK-3beta. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00644-9