4-<2-(N-benzyl-N-propylamino)ethyl>-2-indolone | 735245-67-7

• 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: 4-<2-(N-benzyl-N-propylamino)ethyl>-2-indolone
• 英文别名: 4-[2-[Benzyl(propyl)amino]ethyl]-1,3-dihydroindol-2-one
• CAS: 735245-67-7
• 化学式: C₂₀H₂₄N₂O
• 分子量: 308.423
• InChiKey: DNKQANGZQDJWGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-<2-(N-benzyl-N-propylamino)ethyl>-2-indolone 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 1,3-二氢-4-[2-(丙基氨基)乙基]-2H-吲哚-2-酮
  参考文献：
  名称：

  Synthesis of 4-N,N-dialkylaminoethyl-2-indolones as potential dopamine agonists

  摘要：

  A set of fourteen 4-(2-[N-propyl-N-alkyl-(or alkylaryl-) amino]ethyl)-2-indolone analogues of dopamine were synthesized in 15 steps and evaluated for their affinities towards the D-2 receptor using [H-3]sulpiride or [H-3]spiperone as radioligands. Six analogues displayed D-2 agonist activities comparable (K-i = 450650 nM) to Ropinirole or SK&F 101468. The functionalized amino side chain introduced in the 4-position can be used to modulate the lipophilicity of the analogues without significantly affecting D-2 activity.

  DOI：

  10.1016/0223-5234(96)88317-6
• 作为产物：
  描述：

  2-甲基-3-硝基苯乙酸 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 氯化亚砜 、 potassium ethoxide 、 氢气 、 双氧水 、 sodium carbonate 、 diborane(6) 作用下， 以 甲醇 、 乙醚 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 41.5h， 生成 4-<2-(N-benzyl-N-propylamino)ethyl>-2-indolone
  参考文献：
  名称：

  Synthesis of 4-N,N-dialkylaminoethyl-2-indolones as potential dopamine agonists

  摘要：

  A set of fourteen 4-(2-[N-propyl-N-alkyl-(or alkylaryl-) amino]ethyl)-2-indolone analogues of dopamine were synthesized in 15 steps and evaluated for their affinities towards the D-2 receptor using [H-3]sulpiride or [H-3]spiperone as radioligands. Six analogues displayed D-2 agonist activities comparable (K-i = 450650 nM) to Ropinirole or SK&F 101468. The functionalized amino side chain introduced in the 4-position can be used to modulate the lipophilicity of the analogues without significantly affecting D-2 activity.

  DOI：

  10.1016/0223-5234(96)88317-6

文献信息

• Synthesis of 4-N,N-dialkylaminoethyl-2-indolones as potential dopamine agonists
  作者：A Namil、M Benoit-Guyod、G Leclerc

  DOI：10.1016/0223-5234(96)88317-6

  日期：1995.1

  A set of fourteen 4-(2-[N-propyl-N-alkyl-(or alkylaryl-) amino]ethyl)-2-indolone analogues of dopamine were synthesized in 15 steps and evaluated for their affinities towards the D-2 receptor using [H-3]sulpiride or [H-3]spiperone as radioligands. Six analogues displayed D-2 agonist activities comparable (K-i = 450650 nM) to Ropinirole or SK&F 101468. The functionalized amino side chain introduced in the 4-position can be used to modulate the lipophilicity of the analogues without significantly affecting D-2 activity.