N-[4-(1,2,3,4-tetrahydroisoquinolin-2-yl)butyl]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-[4-(1,2,3,4-tetrahydroisoquinolin-2-yl)butyl]benzenesulfonamide
• 英文别名: N-[4-(3,4-dihydro-1H-isoquinolin-2-yl)butyl]benzenesulfonamide
• 化学式: C₁₉H₂₄N₂O₂S
• 分子量: 344.478
• InChiKey: VEMYZYFRYSMCNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 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-[4-(1,2,3,4-tetrahydroisoquinolin-2-yl)butyl]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-[4-(1,2,3,4-tetrahydroisoquinolin-2-yl)butyl]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：

  苯磺酰氯 、 2(1H)-异喹啉丁胺,3,4-二氢- 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.5h， 以74%的产率得到N-[4-(1,2,3,4-tetrahydroisoquinolin-2-yl)butyl]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：Torrens Jover Antoni

  公开号：US20090163542A1

  公开（公告）日：2009-06-25

  The invention relates to compounds having pharmacological activity towards the 5-HT7 receptor, and more particularly to some tetrahydroisoquinoline substituted 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.
• US7211585B2
  申请人：——

  公开号：US7211585B2

  公开（公告）日：2007-05-01
• US8188115B2
  申请人：——

  公开号：US8188115B2

  公开（公告）日：2012-05-29
• 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.