[2-(5-{[4-(4-Nitro-benzenesulfonylamino)-phenylcarbamoyl]-methoxy}-1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester | 1027918-93-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [2-(5-{[4-(4-Nitro-benzenesulfonylamino)-phenylcarbamoyl]-methoxy}-1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[2-[5-[2-[4-[(4-nitrophenyl)sulfonylamino]anilino]-2-oxoethoxy]-1H-indol-3-yl]ethyl]carbamate
• CAS: 1027918-93-9
• 化学式: C₂₉H₃₁N₅O₈S
• 分子量: 609.66
• InChiKey: ISJPWXZQDRGWAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  43
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  193
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [2-(5-{[4-(4-Nitro-benzenesulfonylamino)-phenylcarbamoyl]-methoxy}-1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester 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-(4-nitro-benzenesulfonylamino)-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：

  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