N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-3-phenylpropanamide | 104724-20-1

• 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: N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-3-phenylpropanamide
• CAS: 104724-20-1
• 化学式: C₂₀H₂₂N₂O₂
• 分子量: 322.407
• InChiKey: OURCZLIOSMCDGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 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：
  54.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-3-phenylpropanamide 在 aluminium hydride 作用下， 以 乙醚 为溶剂， 反应 5.0h， 生成 [2-(5-Methoxy-1H-indol-3-yl)-ethyl]-(3-phenyl-propyl)-amine
  参考文献：
  名称：

  Influence of Amine Substituents on 5-HT2A versus 5-HT2C Binding of Phenylalkyl- and Indolylalkylamines

  摘要：

  The effect of 15 different amine substituents on 5-HT2A and 5-HT2C serotonin receptor binding was investigated for two series of compounds (i.e., phenylalkylamine and indolylalkylamine derivatives). In general, amine substitution decreases receptor affinity; however, N-(4-bromobenzyl) substitution results in compounds that bind at 5-HT2A receptors with high affinity (K-i < 1 nM) and with >100-fold selectivity. Although parallel structural modifications in the two series result in parallel shifts in 5-HT2C binding, these same modifications alter 5-HT2A binding in a less consistent manner.

  DOI：

  10.1021/jm00039a004
• 作为产物：
  描述：

  3-苯基丙酸 在 硫酸 、 palladium diacetate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.75h， 生成 N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-3-phenylpropanamide
  参考文献：
  名称：

  Multi-gram preparation of cinnamoyl tryptamines as skin whitening agents through a chemo-enzymatic flow process

  摘要：

  DOI：

  10.1016/j.tetlet.2021.153453

文献信息

• Synthesis and hypoglycemic activity of N-acyl-5-methoxytryptamines
  作者：L. M. Grin、L. N. Khlaponina、N. S. Pivnenko、A. G. Selichenko、V. D. Brutov

  DOI：10.1007/bf00776330

  日期：1986.7
• Influence of Amine Substituents on 5-HT2A versus 5-HT2C Binding of Phenylalkyl- and Indolylalkylamines
  作者：Richard A. Glennon、Malgorzata Dukat、Mohamed El-Bermawy、Ho Law、Joseph De Los Angeles、Milt Teitler、Allison King、Katharine Herrick-Davis

  DOI：10.1021/jm00039a004

  日期：1994.6

  The effect of 15 different amine substituents on 5-HT2A and 5-HT2C serotonin receptor binding was investigated for two series of compounds (i.e., phenylalkylamine and indolylalkylamine derivatives). In general, amine substitution decreases receptor affinity; however, N-(4-bromobenzyl) substitution results in compounds that bind at 5-HT2A receptors with high affinity (K-i < 1 nM) and with >100-fold selectivity. Although parallel structural modifications in the two series result in parallel shifts in 5-HT2C binding, these same modifications alter 5-HT2A binding in a less consistent manner.
• Multi-gram preparation of cinnamoyl tryptamines as skin whitening agents through a chemo-enzymatic flow process
  作者：David Roura Padrosa、Martina L. Contente

  DOI：10.1016/j.tetlet.2021.153453

  日期：2021.12