N-[[1-[2-(2-phenylphenoxy)ethyl]piperidin-4-yl]methyl]quinoline-2-carboxamide | 1414264-03-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-[[1-[2-(2-phenylphenoxy)ethyl]piperidin-4-yl]methyl]quinoline-2-carboxamide
• CAS: 1414264-03-1
• 化学式: C₃₀H₃₁N₃O₂
• 分子量: 465.595
• InChiKey: LUXFPHQVVHGATF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  54.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  邻苯基苯酚 在 polystyrene carboxaldehyde resin 、 sodium cyanoborohydride 、 potassium carbonate 、 溶剂黄146 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 26.0h， 生成 N-[[1-[2-(2-phenylphenoxy)ethyl]piperidin-4-yl]methyl]quinoline-2-carboxamide
  参考文献：
  名称：

  The multiobjective based design, synthesis and evaluation of the arylsulfonamide/amide derivatives of aryloxyethyl- and arylthioethyl- piperidines and pyrrolidines as a novel class of potent 5-HT7 receptor antagonists

  摘要：

  An analysis of the virtual combinatorial library was used for refining a pilot set of 34 derivatives and designing a targeted 38-member library of the arylamide and arylsulfonamide derivatives of aryloxyethyl- and arylthioethyl-piperidines and pyrrolidines. All compounds 24-95 were synthesized according to an elaborated parallel solid-phase method and were biologically evaluated for their affinity for 5-HT7R. Additionally, the targeted library members were tested for 5-HT1A, 5-HT6, and D-2 receptors. Selected compounds of particular interest were examined for their intrinsic activity at 5-HT7R in vitro employing a cAMP assay. The study allowed us to identify compound 68 (4-fluoro-N-(1-{2-[(propan-2-yl)phenoxylethyl}piperidin-4-yl) benzenesulfonamide) as a potent 5-HT7R ligand (K-i = 0.3 nM) with strong antagonistic properties (K-b = 1 nM) and a 1450-fold selectivity over 5-HT(1A)Rs. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.07.043

文献信息

• The multiobjective based design, synthesis and evaluation of the arylsulfonamide/amide derivatives of aryloxyethyl- and arylthioethyl- piperidines and pyrrolidines as a novel class of potent 5-HT7 receptor antagonists
  作者：Paweł Zajdel、Rafał Kurczab、Katarzyna Grychowska、Grzegorz Satała、Maciej Pawłowski、Andrzej J. Bojarski

  DOI：10.1016/j.ejmech.2012.07.043

  日期：2012.10

  An analysis of the virtual combinatorial library was used for refining a pilot set of 34 derivatives and designing a targeted 38-member library of the arylamide and arylsulfonamide derivatives of aryloxyethyl- and arylthioethyl-piperidines and pyrrolidines. All compounds 24-95 were synthesized according to an elaborated parallel solid-phase method and were biologically evaluated for their affinity for 5-HT7R. Additionally, the targeted library members were tested for 5-HT1A, 5-HT6, and D-2 receptors. Selected compounds of particular interest were examined for their intrinsic activity at 5-HT7R in vitro employing a cAMP assay. The study allowed us to identify compound 68 (4-fluoro-N-(1-2-[(propan-2-yl)phenoxylethyl}piperidin-4-yl) benzenesulfonamide) as a potent 5-HT7R ligand (K-i = 0.3 nM) with strong antagonistic properties (K-b = 1 nM) and a 1450-fold selectivity over 5-HT(1A)Rs. (C) 2012 Elsevier Masson SAS. All rights reserved.