ethyl 4-{1-[(4-tert-butyl)benzyl]-4-hydroxy-1H-indol-3-yl}-2-hydroxy-4-oxobut-2-enoate | 1580497-16-0

• 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: ethyl 4-{1-[(4-tert-butyl)benzyl]-4-hydroxy-1H-indol-3-yl}-2-hydroxy-4-oxobut-2-enoate
• CAS: 1580497-16-0
• 化学式: C₂₅H₂₇NO₅
• 分子量: 421.493
• InChiKey: RIGBFBLYWWQSBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.88
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  88.76
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl 4-{1-[(4-tert-butyl)benzyl]-4-hydroxy-1H-indol-3-yl}-2-hydroxy-4-oxobut-2-enoate 在 sodium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 1.5h， 以74%的产率得到4-{1-[4-(tert-butyl)benzyl]-4-hydroxy-1H-indol-3-yl}-2-hydroxy-4-oxobut-2-enoic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of novel antiviral agents as protein–protein interaction inhibitors

  摘要：

  In continuation of our research efforts toward the identification and optimization for novel inhibitors of interaction between human immunodeficiency virus type 1 integrase and cellular cofactor LEDGF/p75, we designed and synthesized a new series of 4-benzylindole derivatives. Most of the title compounds proved to be able to block this protein-protein interaction (PPI), with a percentage ranging from 30% to 90% at 100 mu M. The most promising derivative was compound 10b showing IC50 value of 6.41 mu M. The main structure-activity relationships (SAR) are discussed and rationalized by docking studies.

  DOI：

  10.3109/14756366.2013.766609
• 作为产物：
  描述：

  4-羟基吲哚 在 sodium methylate 、 potassium carbonate 、 三氯氧磷 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.23h， 生成 ethyl 4-{1-[(4-tert-butyl)benzyl]-4-hydroxy-1H-indol-3-yl}-2-hydroxy-4-oxobut-2-enoate
  参考文献：
  名称：

  Synthesis and biological evaluation of novel antiviral agents as protein–protein interaction inhibitors

  摘要：

  In continuation of our research efforts toward the identification and optimization for novel inhibitors of interaction between human immunodeficiency virus type 1 integrase and cellular cofactor LEDGF/p75, we designed and synthesized a new series of 4-benzylindole derivatives. Most of the title compounds proved to be able to block this protein-protein interaction (PPI), with a percentage ranging from 30% to 90% at 100 mu M. The most promising derivative was compound 10b showing IC50 value of 6.41 mu M. The main structure-activity relationships (SAR) are discussed and rationalized by docking studies.

  DOI：

  10.3109/14756366.2013.766609