(E)-3-[3-(2-tert-Butoxycarbonylamino-ethyl)-1H-indol-5-yl]-acrylic acid methyl ester | 780730-95-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-3-[3-(2-tert-Butoxycarbonylamino-ethyl)-1H-indol-5-yl]-acrylic acid methyl ester
• 英文别名: methyl 3-[3-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]-1H-indol-5-yl]prop-2-enoate
• CAS: 780730-95-2
• 化学式: C₁₉H₂₄N₂O₄
• 分子量: 344.411
• InChiKey: MBZGHXQHYWRYID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  80.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-3-[3-(2-tert-Butoxycarbonylamino-ethyl)-1H-indol-5-yl]-acrylic acid methyl ester 在 palladium on activated charcoal 氢氧化钾 、 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 7.0h， 生成 3-[3-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]-1H-indol-5-yl]propanoic acid
  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：

  丙烯酸甲酯（MA） 、 [2-(5-溴-1H-吲哚-3-基)-乙基]-氨基甲酸叔丁酯 在 palladium diacetate 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以86%的产率得到(E)-3-[3-(2-tert-Butoxycarbonylamino-ethyl)-1H-indol-5-yl]-acrylic acid methyl ester
  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