1-(2-氨基-3-丙基苯基)-2-氯乙烷酮 | 128600-54-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(2-氨基-3-丙基苯基)-2-氯乙烷酮
• 中文别名: 环丁烷羧酸1-氨基-2-甲基-(1R，2S)-(9CI)
• 英文名称: 1-(2-Amino-3-propyl-phenyl)-2-chloro-ethanone
• 英文别名: 1-(2-Amino-3-propylphenyl)-2-chloroethanone
• CAS: 128600-54-4
• 化学式: C₁₁H₁₄ClNO
• 分子量: 211.691
• InChiKey: VHEQSDFVRHJIQC-UHFFFAOYSA-N

物化性质

• 熔点：
  60-61 °C
• 沸点：
  349.2±32.0 °C(Predicted)
• 密度：
  1.150±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-氨基-3-丙基苯基)-2-氯乙烷酮 在 sodium tetrahydroborate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 6.0h， 生成 7-n-propylindole
  参考文献：
  名称：

  Binding of indolylalkylamines at 5-HT2 serotonin receptors: examination of a hydrophobic binding region

  摘要：

  Taking advantage of a proposed hydrophobic region on 5-HT2 receptors previously identified by radioligand-binding studies utilizing various phenylisopropylamine derivatives, we prepared and evaluated several N1 - and/or C7-alkyl-substituted derivatives of alpha-methyltryptamine in order to improve its affinity and selectivity. It was determined that substitution of an n-propyl or amyl group has similar effect on affinity regardless of location (i.e., N1 or C7). The low affinity of several N1-alkylpyrroleethylamines suggests that the benzene portion of the alpha-methyltryptamines is necessary for significant affinity. Whereas tryptamine derivatives generally display little selectivity for the various populations of 5-HT receptors, N1-n-propyl-5-methoxy-alpha-methyltryptamine (3h) binds with significant affinity (Ki = 12 nM) and selectivity at 5-HT2 receptors relative to 5-HT1A (Ki = 7100 nM), 5-HT1B (Ki = 5000 nM), 5-HT1C (Ki = 120 nM), and 5-HT1D (Ki greater than 10,000 nM) receptors. As a consequence, this is the most 5-HT2-selective indolylalkylamine derivative reported to date.

  DOI：

  10.1021/jm00172a016
• 作为产物：
  描述：

  氯乙腈 、 2-丙基苯胺 在 三氯化铝 、 三氯化硼 作用下， 生成 1-(2-氨基-3-丙基苯基)-2-氯乙烷酮
  参考文献：
  名称：

  Binding of indolylalkylamines at 5-HT2 serotonin receptors: examination of a hydrophobic binding region

  摘要：

  Taking advantage of a proposed hydrophobic region on 5-HT2 receptors previously identified by radioligand-binding studies utilizing various phenylisopropylamine derivatives, we prepared and evaluated several N1 - and/or C7-alkyl-substituted derivatives of alpha-methyltryptamine in order to improve its affinity and selectivity. It was determined that substitution of an n-propyl or amyl group has similar effect on affinity regardless of location (i.e., N1 or C7). The low affinity of several N1-alkylpyrroleethylamines suggests that the benzene portion of the alpha-methyltryptamines is necessary for significant affinity. Whereas tryptamine derivatives generally display little selectivity for the various populations of 5-HT receptors, N1-n-propyl-5-methoxy-alpha-methyltryptamine (3h) binds with significant affinity (Ki = 12 nM) and selectivity at 5-HT2 receptors relative to 5-HT1A (Ki = 7100 nM), 5-HT1B (Ki = 5000 nM), 5-HT1C (Ki = 120 nM), and 5-HT1D (Ki greater than 10,000 nM) receptors. As a consequence, this is the most 5-HT2-selective indolylalkylamine derivative reported to date.

  DOI：

  10.1021/jm00172a016

文献信息

• GLENNON, RICHARD A.;CHAURASIA, CHANDRA;TITELER, MILT, J. MED. CHEM., 33,(1990) N0, C. 2777-2784
  作者：GLENNON, RICHARD A.、CHAURASIA, CHANDRA、TITELER, MILT

  DOI：——

  日期：——
• Binding of indolylalkylamines at 5-HT2 serotonin receptors: examination of a hydrophobic binding region
  作者：Richard A. Glennon、Chandra Chaurasia、Milt Titeler

  DOI：10.1021/jm00172a016

  日期：1990.10

  Taking advantage of a proposed hydrophobic region on 5-HT2 receptors previously identified by radioligand-binding studies utilizing various phenylisopropylamine derivatives, we prepared and evaluated several N1 - and/or C7-alkyl-substituted derivatives of alpha-methyltryptamine in order to improve its affinity and selectivity. It was determined that substitution of an n-propyl or amyl group has similar effect on affinity regardless of location (i.e., N1 or C7). The low affinity of several N1-alkylpyrroleethylamines suggests that the benzene portion of the alpha-methyltryptamines is necessary for significant affinity. Whereas tryptamine derivatives generally display little selectivity for the various populations of 5-HT receptors, N1-n-propyl-5-methoxy-alpha-methyltryptamine (3h) binds with significant affinity (Ki = 12 nM) and selectivity at 5-HT2 receptors relative to 5-HT1A (Ki = 7100 nM), 5-HT1B (Ki = 5000 nM), 5-HT1C (Ki = 120 nM), and 5-HT1D (Ki greater than 10,000 nM) receptors. As a consequence, this is the most 5-HT2-selective indolylalkylamine derivative reported to date.