ethyl N-ethyl-4,7-dioxo-6-(4-methoxyphenoxy)-4,7-dihydro-1H-indole-2-carboxylate

• 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 N-ethyl-4,7-dioxo-6-(4-methoxyphenoxy)-4,7-dihydro-1H-indole-2-carboxylate
• 英文别名: Ethyl 1-ethyl-6-(4-methoxyphenoxy)-4,7-dioxoindole-2-carboxylate；ethyl 1-ethyl-6-(4-methoxyphenoxy)-4,7-dioxoindole-2-carboxylate
• 化学式: C₂₀H₁₉NO₆
• 分子量: 369.374
• InChiKey: FETNRNSFEPONMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  83.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-溴-2,5-二甲氧基苯甲醛 在 silver(II) oxide 、 乙醇 、 硝酸 、 sodium 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 16.75h， 生成 ethyl N-ethyl-4,7-dioxo-6-(4-methoxyphenoxy)-4,7-dihydro-1H-indole-2-carboxylate
  参考文献：
  名称：

  Synthesis and biological characterization of new aryloxyindole-4,9-diones as potent trypanosomicidal agents

  摘要：

  A new indole-4,9-dione and their phenoxy derivatives were synthesized and evaluated in vitro against the epimastigote form of Trypanosoma cruzi, Y strain. All of these novel compounds were found to be extremely potent and selective that the standard drug nifurtimox. Interestingly, phenoxyindole-4,9-dione 9d displayed excellent nanomolar inhibitory activity, IC50=20 nM, and high selectivity index, SI=625. In silico studies using MOE program were performed to generate a preliminary pharmacophore model.

  DOI：

  10.1016/j.bmcl.2014.06.044

文献信息

• Synthesis and biological characterization of new aryloxyindole-4,9-diones as potent trypanosomicidal agents
  作者：Ricardo A. Tapia、Cristian O. Salas、Karina Vázquez、Christian Espinosa-Bustos、Jorge Soto-Delgado、Javier Varela、Estefanía Birriel、Hugo Cerecetto、Mercedes González、Margot Paulino

  DOI：10.1016/j.bmcl.2014.06.044

  日期：2014.8

  A new indole-4,9-dione and their phenoxy derivatives were synthesized and evaluated in vitro against the epimastigote form of Trypanosoma cruzi, Y strain. All of these novel compounds were found to be extremely potent and selective that the standard drug nifurtimox. Interestingly, phenoxyindole-4,9-dione 9d displayed excellent nanomolar inhibitory activity, IC50=20 nM, and high selectivity index, SI=625. In silico studies using MOE program were performed to generate a preliminary pharmacophore model.