2-(3-{2-[N-(tert-butoxycarbonyl)amino]ethyl}-1H-indol-5-yloxy)-N-(4-aminomethylphenyl)acetamide | 189288-97-9

• 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: 2-(3-{2-[N-(tert-butoxycarbonyl)amino]ethyl}-1H-indol-5-yloxy)-N-(4-aminomethylphenyl)acetamide
• 英文别名: tert-butyl N-[2-[5-[2-[4-(aminomethyl)anilino]-2-oxoethoxy]-1H-indol-3-yl]ethyl]carbamate
• CAS: 189288-97-9
• 化学式: C₂₄H₃₀N₄O₄
• 分子量: 438.527
• InChiKey: BWDWPEQUBCWMLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  119
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(3-{2-[N-(tert-butoxycarbonyl)amino]ethyl}-1H-indol-5-yloxy)-N-(4-aminomethylphenyl)acetamide 在 三氟乙酸 作用下， 以 甲苯 为溶剂， 生成 2-[3-(2-Amino-ethyl)-1H-indol-5-yloxy]-N-(4-aminomethyl-phenyl)-acetamide; hydrochloride
  参考文献：
  名称：

  Synthesis, binding affinity and intrinsic activity of new anilide derivatives of serotonin at human 5-HT1D receptors

  摘要：

  The design and synthesis of a new series of anilide derivatives of serotonin is described. Binding affinity and intrinsic activity were evaluated at cloned human 5-HT1D alpha, 5-HT1D beta and 5-HT1A receptors. Modification of the terminal substituent on the aromatic moiety (R(1)) was investigated and optimal affinity, activity and selectivity for 5-HT1D versus 5-HT1A receptors were obtained for the sulfonamide derivatives 9 and 10. Functional activity was also assessed in the New Zealand white rabbit saphenous vein contraction model, in which most of the compounds behaved as full agonists. Further structural modifications are also described, eg, replacement of the oxygen for carbon atom at the 5-position of the tryptamine moiety or terminal N-dimethylation.

  DOI：

  10.1016/s0223-5234(97)87539-3
• 作为产物：
  描述：

  N-叔-丁基氧羰基血清素 在 镍 ammonium hydroxide 、 氢气 、 caesium carbonate 、 potassium iodide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 25.0~60.0 ℃ 、101.33 kPa 条件下， 反应 103.0h， 生成 2-(3-{2-[N-(tert-butoxycarbonyl)amino]ethyl}-1H-indol-5-yloxy)-N-(4-aminomethylphenyl)acetamide
  参考文献：
  名称：

  Synthesis, binding affinity and intrinsic activity of new anilide derivatives of serotonin at human 5-HT1D receptors

  摘要：

  The design and synthesis of a new series of anilide derivatives of serotonin is described. Binding affinity and intrinsic activity were evaluated at cloned human 5-HT1D alpha, 5-HT1D beta and 5-HT1A receptors. Modification of the terminal substituent on the aromatic moiety (R(1)) was investigated and optimal affinity, activity and selectivity for 5-HT1D versus 5-HT1A receptors were obtained for the sulfonamide derivatives 9 and 10. Functional activity was also assessed in the New Zealand white rabbit saphenous vein contraction model, in which most of the compounds behaved as full agonists. Further structural modifications are also described, eg, replacement of the oxygen for carbon atom at the 5-position of the tryptamine moiety or terminal N-dimethylation.

  DOI：

  10.1016/s0223-5234(97)87539-3