N-[2-(1,2,3,4-tetrahydroisoquinolin-2-yl)ethyl]benzenesulfonamide | 1124094-03-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: N-[2-(1,2,3,4-tetrahydroisoquinolin-2-yl)ethyl]benzenesulfonamide
• 英文别名: N-[2-(3,4-dihydro-1H-isoquinolin-2-yl)ethyl]benzenesulfonamide
• CAS: 1124094-03-6
• 化学式: C₁₇H₂₀N₂O₂S
• 分子量: 316.424
• InChiKey: FMKAPYBPKCETEH-UHFFFAOYSA-N

物化性质

• 沸点：
  487.6±47.0 °C(predicted)
• 密度：
  1.217±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[2-(1,2,3,4-tetrahydroisoquinolin-2-yl)ethyl]benzenesulfonamide 在 四丁基溴化铵 、 potassium carbonate 、 sodium hydroxide 、 肼 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 23.0h， 生成 N-(3-aminopropyl)-N-[2-(1,2,3,4-tetrahydroisoquinolin-2-yl)ethyl]benzenesulfonamide
  参考文献：
  名称：

  Arene- and quinoline-sulfonamides as novel 5-HT7 receptor ligands

  摘要：

  Novel arene- and quinolinesulfonamides were synthesized using different solutions and a solid-support methodology, and were evaluated for their affinity for 5-HT1A, 5-HT2A, 5-HT6, and 5-HT7 receptors. Compound 54 (N-Ethyl-N-[4-(1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinolin-2-yl)butyl]-8-quinolinesulfonamide) was identified as potent 5-HT7 antagonist (K-i = 13 nM, K-B = 140 nM) with good selectivity over 5-HT1A, 5-HT2A, 5-HT6 receptors. In the FST in mice, it reduced immobility in a manner similar to the selective 5-HT7 antagonist SB-269970. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.09.044
• 作为产物：
  描述：

  2-(3,4-二氢异喹啉-2(1H)-基)乙胺 、 苯磺酰氯 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.5h， 以39%的产率得到N-[2-(1,2,3,4-tetrahydroisoquinolin-2-yl)ethyl]benzenesulfonamide
  参考文献：
  名称：

  Arene- and quinoline-sulfonamides as novel 5-HT7 receptor ligands

  摘要：

  Novel arene- and quinolinesulfonamides were synthesized using different solutions and a solid-support methodology, and were evaluated for their affinity for 5-HT1A, 5-HT2A, 5-HT6, and 5-HT7 receptors. Compound 54 (N-Ethyl-N-[4-(1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinolin-2-yl)butyl]-8-quinolinesulfonamide) was identified as potent 5-HT7 antagonist (K-i = 13 nM, K-B = 140 nM) with good selectivity over 5-HT1A, 5-HT2A, 5-HT6 receptors. In the FST in mice, it reduced immobility in a manner similar to the selective 5-HT7 antagonist SB-269970. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.09.044