4-(4-{2-[4-(4-chlorophenyl)piperazin-1-yl]ethyl}piperidine-1-sulfonyl)isoquinoline hydrochloride | 1360625-64-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 4-(4-{2-[4-(4-chlorophenyl)piperazin-1-yl]ethyl}piperidine-1-sulfonyl)isoquinoline hydrochloride
• 英文别名: 4-[4-[2-[4-(4-Chlorophenyl)piperazin-1-yl]ethyl]piperidin-1-yl]sulfonylisoquinoline;hydrochloride
• CAS: 1360625-64-4
• 化学式: C₂₆H₃₁ClN₄O₂S*ClH
• 分子量: 535.538
• InChiKey: FUMFBOOKIXYDBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.92
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  65.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-Boc-4-哌啶乙醇 在 吡啶 、 盐酸 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 33.0h， 生成 4-(4-{2-[4-(4-chlorophenyl)piperazin-1-yl]ethyl}piperidine-1-sulfonyl)isoquinoline hydrochloride
  参考文献：
  名称：

  Quinoline- and isoquinoline-sulfonamide derivatives of LCAP as potent CNS multi-receptor—5-HT1A/5-HT2A/5-HT7 and D2/D3/D4—agents: The synthesis and pharmacological evaluation

  摘要：

  Two series of arylpiperazinyl-alkyl quinoline-, isoquinoline-, naphthalene-sulfonamides with flexible (13-26) and semi-rigid (33-36) alkylene spacer were synthesized and evaluated for 5-HT1A, 5-HT2A, 5-HT6, 5-HT7 and selected compounds for D-2, D-3, D-4 receptors. The compounds with a mixed 5-HT and D receptors profile 16 (N-{4-[4-(3-chlorophenyl)-piperazin-1-yl]-butyl}-3-quinolinesulfonamide) and 36 (4-(4-{2-[4-(4-chloro-phenyl)-piperazin-1-yl]-ethyl}-piperidine-1-sulfonyl)-isoquinoline), displaying antagonistic activity at 5-HT7, 5-HT2A, D2 postsynaptic sites, produced antidepressant-like effects in the forced swim test in mice and showed significant anxiolytic activity in the plus-maze test in rats. The lead compound 36, a multi-receptor 5-HT2A/5-HT7/D-2/D-3/D-4 agent, also displayed significant antipsychotic properties in the MK-801-induced hyperlocomotor activity in mice. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.12.039

文献信息

• Quinoline- and isoquinoline-sulfonamide derivatives of LCAP as potent CNS multi-receptor—5-HT1A/5-HT2A/5-HT7 and D2/D3/D4—agents: The synthesis and pharmacological evaluation
  作者：Paweł Zajdel、Krzysztof Marciniec、Andrzej Maślankiewicz、Grzegorz Satała、Beata Duszyńska、Andrzej J. Bojarski、Anna Partyka、Magdalena Jastrzębska-Więsek、Dagmara Wróbel、Anna Wesołowska、Maciej Pawłowski

  DOI：10.1016/j.bmc.2011.12.039

  日期：2012.2

  Two series of arylpiperazinyl-alkyl quinoline-, isoquinoline-, naphthalene-sulfonamides with flexible (13-26) and semi-rigid (33-36) alkylene spacer were synthesized and evaluated for 5-HT1A, 5-HT2A, 5-HT6, 5-HT7 and selected compounds for D-2, D-3, D-4 receptors. The compounds with a mixed 5-HT and D receptors profile 16 (N-4-[4-(3-chlorophenyl)-piperazin-1-yl]-butyl}-3-quinolinesulfonamide) and 36 (4-(4-2-[4-(4-chloro-phenyl)-piperazin-1-yl]-ethyl}-piperidine-1-sulfonyl)-isoquinoline), displaying antagonistic activity at 5-HT7, 5-HT2A, D2 postsynaptic sites, produced antidepressant-like effects in the forced swim test in mice and showed significant anxiolytic activity in the plus-maze test in rats. The lead compound 36, a multi-receptor 5-HT2A/5-HT7/D-2/D-3/D-4 agent, also displayed significant antipsychotic properties in the MK-801-induced hyperlocomotor activity in mice. (C) 2011 Elsevier Ltd. All rights reserved.