N-[3-(1,2,3,4-tetrahydroisoquinolin-2-yl)propyl]benzenesulfonamide

• 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-[3-(1,2,3,4-tetrahydroisoquinolin-2-yl)propyl]benzenesulfonamide
• 英文别名: N-[3-(3,4-dihydroisoquinolin-2(1H)-yl)propyl]benzenesulfonamide；N-[3-(3,4-dihydro-1H-isoquinolin-2-yl)propyl]benzenesulfonamide
• 化学式: C₁₈H₂₂N₂O₂S
• 分子量: 330.451
• InChiKey: NNJCGFLNBBECHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 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-[3-(1,2,3,4-tetrahydroisoquinolin-2-yl)propyl]benzenesulfonamide 在 四丁基溴化铵 、 potassium carbonate 、 sodium hydroxide 、 肼 作用下， 以 乙醇 、 丙酮 、 甲苯 为溶剂， 反应 23.0h， 生成 N-(3-aminopropyl)-N-[3-(1,2,3,4-tetrahydroisoquinolin-2-yl)propyl]benzenesulfonamide fumarate
  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：

  3-(3,4-二氢异喹啉-2(1h)-基)丙烷-1-胺 、 苯磺酰氯 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.5h， 以65%的产率得到N-[3-(1,2,3,4-tetrahydroisoquinolin-2-yl)propyl]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

文献信息

• 5-HT7 receptor antagonists
  申请人：LABORATORIOS DEL DR. ESTEVE, S.A.

  公开号：EP1630159A1

  公开（公告）日：2006-03-01

  The invention relates to compounds of formula (I): having pharmacological activity towards the 5-HT7 receptor, and more particularly to some tetrahydroisoquinoline propyl sulfonamide compounds, to processes of preparation of such compounds, to pharmaceutical compositions comprising them, and to their use for the treatment and or prophylaxis of a disease in which 5-HT is involved, such as CNS disorders.

  本发明涉及式 (I) 的化合物： 本发明涉及对 5-HT7 受体具有药理活性的化合物，特别是一些四氢异喹啉丙基磺酰胺化合物，涉及此类化合物的制备工艺，涉及包含这些化合物的药物组合物，还涉及它们在治疗和预防涉及 5-HT 的疾病（如中枢神经系统疾病）方面的用途。
• 5-ht7 receptor antagonists
  申请人：Torrens Jover Antoni

  公开号：US20090088450A1

  公开（公告）日：2009-04-02

  The invention relates to compounds having pharmacological activity towards the 5-HT7 receptor, and more particularly to some tetrahydroisoquinoline propyl sulfonamide compounds, to processes of preparation of such compounds, to pharmaceutical compositions comprising them, and to their use for the treatment and or prophylaxis of a disease in which 5-HT is involved, such as CNS disorders.
• US7211584B2
  申请人：——

  公开号：US7211584B2

  公开（公告）日：2007-05-01
• US8148397B2
  申请人：——

  公开号：US8148397B2

  公开（公告）日：2012-04-03
• Arene- and quinoline-sulfonamides as novel 5-HT7 receptor ligands
  作者：Paweł Zajdel、Krzysztof Marciniec、Andrzej Maślankiewicz、Maria H. Paluchowska、Grzegorz Satała、Anna Partyka、Magdalena Jastrzębska-Więsek、Dagmara Wróbel、Anna Wesołowska、Beata Duszyńska、Andrzej J. Bojarski、Maciej Pawłowski

  DOI：10.1016/j.bmc.2011.09.044

  日期：2011.11

  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.