3-fluoro-N-(1-{2-[(propan-2-yl)phenoxy]ethyl}piperidin-4-yl)-N-cyclopropylmethyl-benzenesulfonamide

• 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: 3-fluoro-N-(1-{2-[(propan-2-yl)phenoxy]ethyl}piperidin-4-yl)-N-cyclopropylmethyl-benzenesulfonamide
• 英文别名: N-(cyclopropylmethyl)-3-fluoro-N-[1-[2-(2-propan-2-ylphenoxy)ethyl]piperidin-4-yl]benzenesulfonamide
• 化学式: C₂₆H₃₅FN₂O₃S
• 分子量: 474.64
• InChiKey: BLDRZOKSSGFKEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  58.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-(2-溴-乙氧基)-2-异丙基-苯 在 potassium carbonate 、 三乙胺 、 三氟乙酸 、 potassium iodide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 55.0h， 生成 3-fluoro-N-(1-{2-[(propan-2-yl)phenoxy]ethyl}piperidin-4-yl)-N-cyclopropylmethyl-benzenesulfonamide
  参考文献：
  名称：

  N-Alkylated arylsulfonamides of (aryloxy)ethyl piperidines: 5-HT7 receptor selectivity versus multireceptor profile

  摘要：

  The N-alkylation of the sulfonamide moiety, in a group of arylsulfonamide derivatives of (aryloxy)ethyl piperidines, may be considered as a strategy for the design of selective 5-HT7 receptor ligands or multifunctional agents to extend a polypharmacological approach to the treatment of complex diseases. The study allowed for the identification of 31 (1-methyl-N-{1-[2-(2-(t-butyl)phenoxy)ethyl]piperidin-4-yl}-N- cyclopropylmethyl-1H-pyrazole-4-sulfonamide), a potent and selective 5-HT7 receptor antagonist and 33 (1-methyl-N-{1-[2-(biphenyl-2-yloxy)ethyl] piperidin-4-yl}-N-cyclopropylmethyl-1H-pyrazole-4-sulfonamide), as multimodal 5-HT/dopamine receptor ligand, as 5-HT2A/5-HT7/D2 receptor antagonists. Both selected compounds were evaluated in vivo in a forced swim test (FST) in mice and in a novel object recognition (NOR) task in rats, demonstrating distinct antidepressant-like and pro-cognitive properties (MED = 1.25 mg/kg and 1 mg/kg, ip, respectively). These findings warrant further studies to explore the therapeutic potential of N-alkylated arylsulfonamides for the treatment of CNS disorders. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.11.041

文献信息

• N-Alkylated arylsulfonamides of (aryloxy)ethyl piperidines: 5-HT7 receptor selectivity versus multireceptor profile
  作者：Vittorio Canale、Rafał Kurczab、Anna Partyka、Grzegorz Satała、Karolina Słoczyńska、Tomasz Kos、Magdalena Jastrzębska-Więsek、Agata Siwek、Elżbieta Pękala、Andrzej J. Bojarski、Anna Wesołowska、Piotr Popik、Paweł Zajdel

  DOI：10.1016/j.bmc.2015.11.041

  日期：2016.1

  The N-alkylation of the sulfonamide moiety, in a group of arylsulfonamide derivatives of (aryloxy)ethyl piperidines, may be considered as a strategy for the design of selective 5-HT7 receptor ligands or multifunctional agents to extend a polypharmacological approach to the treatment of complex diseases. The study allowed for the identification of 31 (1-methyl-N-1-[2-(2-(t-butyl)phenoxy)ethyl]piperidin-4-yl}-N- cyclopropylmethyl-1H-pyrazole-4-sulfonamide), a potent and selective 5-HT7 receptor antagonist and 33 (1-methyl-N-1-[2-(biphenyl-2-yloxy)ethyl] piperidin-4-yl}-N-cyclopropylmethyl-1H-pyrazole-4-sulfonamide), as multimodal 5-HT/dopamine receptor ligand, as 5-HT2A/5-HT7/D2 receptor antagonists. Both selected compounds were evaluated in vivo in a forced swim test (FST) in mice and in a novel object recognition (NOR) task in rats, demonstrating distinct antidepressant-like and pro-cognitive properties (MED = 1.25 mg/kg and 1 mg/kg, ip, respectively). These findings warrant further studies to explore the therapeutic potential of N-alkylated arylsulfonamides for the treatment of CNS disorders. (C) 2015 Elsevier Ltd. All rights reserved.