3-(2-Acetylamino-1-ethoxycarbonyl-ethyl)-indole-1-carboxylic acid ethyl ester | 79772-28-4

• 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: 3-(2-Acetylamino-1-ethoxycarbonyl-ethyl)-indole-1-carboxylic acid ethyl ester
• 英文别名: Ethyl 3-(3-acetamido-1-ethoxy-1-oxopropan-2-yl)indole-1-carboxylate
• CAS: 79772-28-4
• 化学式: C₁₈H₂₂N₂O₅
• 分子量: 346.383
• InChiKey: GVGIXMDLOUUUEL-UHFFFAOYSA-N

物化性质

• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  86.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(2-Acetylamino-1-ethoxycarbonyl-ethyl)-indole-1-carboxylic acid ethyl ester 在 sodium hydroxide 作用下， 反应 8.0h， 以72%的产率得到3-amino-2-(3-indolyl)propionic acid
  参考文献：
  名称：

  Tryptophan analogs. 1. Synthesis and antihypertensive activity of positional isomers

  摘要：

  A series of tryptophan analogues having the carboxyl function at the beta-position was synthesized and tested for antihypertensive activity. The 5-methoxy analogue 46 exhibited antihypertensive activity in the rat via the oral route and was much more potent than the normal tryptophan analogue. The methyl ester was found to be a critical structural feature for activity.

  DOI：

  10.1021/jm00348a022
• 作为产物：
  描述：

  乙酸酐 、 ethyl (1-carboethoxy-1H-indol-3-yl)cyanoacetate 在 Raney Ni (W-4) 氢气 作用下， 以88%的产率得到3-(2-Acetylamino-1-ethoxycarbonyl-ethyl)-indole-1-carboxylic acid ethyl ester
  参考文献：
  名称：

  Tryptophan analogs. 1. Synthesis and antihypertensive activity of positional isomers

  摘要：

  A series of tryptophan analogues having the carboxyl function at the beta-position was synthesized and tested for antihypertensive activity. The 5-methoxy analogue 46 exhibited antihypertensive activity in the rat via the oral route and was much more potent than the normal tryptophan analogue. The methyl ester was found to be a critical structural feature for activity.

  DOI：

  10.1021/jm00348a022

文献信息

• Tryptophan analogs. 1. Synthesis and antihypertensive activity of positional isomers
  作者：Max E. Safdy、Elva Kurchacova、Robert N. Schut、Horacio Vidrio、Enrique Hong

  DOI：10.1021/jm00348a022

  日期：1982.6

  A series of tryptophan analogues having the carboxyl function at the beta-position was synthesized and tested for antihypertensive activity. The 5-methoxy analogue 46 exhibited antihypertensive activity in the rat via the oral route and was much more potent than the normal tryptophan analogue. The methyl ester was found to be a critical structural feature for activity.