2-(3-{2-[N-(tert-butoxycarbonyl)amino]ethyl}-1H-indol-5-yloxy)-N-(4-nitrophenyl)acetamide | 162646-78-8

• 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-nitrophenyl)acetamide
• 英文别名: tert-butyl N-[2-[5-[2-(4-nitroanilino)-2-oxoethoxy]-1H-indol-3-yl]ethyl]carbamate
• CAS: 162646-78-8
• 化学式: C₂₃H₂₆N₄O₆
• 分子量: 454.483
• InChiKey: CTFTVZMJJHXJQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  138
• 氢给体数：
  3
• 氢受体数：
  6

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-nitrophenyl)acetamide 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 4.0h， 生成 [2-(5-{[4-(4-Nitro-benzenesulfonylamino)-phenylcarbamoyl]-methoxy}-1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl 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
• 作为产物：
  描述：

  N-叔-丁基氧羰基血清素 、 2-氯-4’-硝基乙酰苯胺 在 potassium carbonate 、 potassium iodide 作用下， 以 丁酮 为溶剂， 以55%的产率得到2-(3-{2-[N-(tert-butoxycarbonyl)amino]ethyl}-1H-indol-5-yloxy)-N-(4-nitrophenyl)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

文献信息

• Synthesis, binding affinity and intrinsic activity of new anilide derivatives of serotonin at human 5-HT1D receptors
  作者：M Perez、N Ayerbe、C Fourrier、I Sigogneau、PJ Pauwels、C Palmier、GW John、JP Valentin、S Halazy

  DOI：10.1016/s0223-5234(97)87539-3

  日期：1997.1

  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.