(S)-7-(4-(2-isopropylphenyl)piperazin-1-yl)-1-(2-(piperidine-1-carbonyl)pyrrolidin-1-yl)heptan-1-one

• 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: (S)-7-(4-(2-isopropylphenyl)piperazin-1-yl)-1-(2-(piperidine-1-carbonyl)pyrrolidin-1-yl)heptan-1-one
• 英文别名: 1-[(2S)-2-(piperidine-1-carbonyl)pyrrolidin-1-yl]-7-[4-(2-propan-2-ylphenyl)piperazin-1-yl]heptan-1-one
• 化学式: C₃₀H₄₈N₄O₂
• 分子量: 496.737
• InChiKey: AIYQDXGDHMXECI-NDEPHWFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  47.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-哌啶基[(2S)-2-吡咯烷基]甲酮 在 potassium carbonate 、 三乙胺 、 potassium iodide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 84.0h， 生成 (S)-7-(4-(2-isopropylphenyl)piperazin-1-yl)-1-(2-(piperidine-1-carbonyl)pyrrolidin-1-yl)heptan-1-one
  参考文献：
  名称：

  Towards novel 5-HT7 versus 5-HT1A receptor ligands among LCAPs with cyclic amino acid amide fragments: Design, synthesis, and antidepressant properties. Part II

  摘要：

  A 26-membered library of novel long-chain arylpiperazines, which contained primary and tertiary amides of cyclic amino acids (proline and 1,2,3,4-tetrahydroisoquinoline-3-carboxamide) in the terminal fragment was synthesized and biologically evaluated for binding affinity for 5-HT7 and 5-HT1A receptors. Docking studies confirmed advantages of Tic-amide over Pro-amide fragment for interaction with 5-HT7 receptors. Selected compounds 32 and 28, which behaved as 5-HT(7)Rs antagonist and 5-HT1A partial agonist, respectively, produced antidepressant-like effects in the forced swim test in mice after acute treatment in doses of 10 mg/kg (32) and 1.25 mg/kg (28). Compound 32 reduced immobility in a manner similar to the selective 5-HT7 antagonist SB-269970. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.12.041

文献信息

• Towards novel 5-HT7 versus 5-HT1A receptor ligands among LCAPs with cyclic amino acid amide fragments: Design, synthesis, and antidepressant properties. Part II
  作者：Vittorio Canale、Rafał Kurczab、Anna Partyka、Grzegorz Satała、Jagna Witek、Magdalena Jastrzębska-Więsek、Maciej Pawłowski、Andrzej J. Bojarski、Anna Wesołowska、Paweł Zajdel

  DOI：10.1016/j.ejmech.2014.12.041

  日期：2015.3

  A 26-membered library of novel long-chain arylpiperazines, which contained primary and tertiary amides of cyclic amino acids (proline and 1,2,3,4-tetrahydroisoquinoline-3-carboxamide) in the terminal fragment was synthesized and biologically evaluated for binding affinity for 5-HT7 and 5-HT1A receptors. Docking studies confirmed advantages of Tic-amide over Pro-amide fragment for interaction with 5-HT7 receptors. Selected compounds 32 and 28, which behaved as 5-HT(7)Rs antagonist and 5-HT1A partial agonist, respectively, produced antidepressant-like effects in the forced swim test in mice after acute treatment in doses of 10 mg/kg (32) and 1.25 mg/kg (28). Compound 32 reduced immobility in a manner similar to the selective 5-HT7 antagonist SB-269970. (C) 2014 Elsevier Masson SAS. All rights reserved.