1-(4-{4-[4-(2-isopropoxyphenyl)-1-piperazinyl]-4-hydroxybutyl}benzoyl)piperidine | 148853-54-7

• 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: 1-(4-{4-[4-(2-isopropoxyphenyl)-1-piperazinyl]-4-hydroxybutyl}benzoyl)piperidine
• 英文别名: [4-[1-Hydroxy-4-[4-(2-propan-2-yloxyphenyl)piperazin-1-yl]butyl]phenyl]-piperidin-1-ylmethanone
• CAS: 148853-54-7
• 化学式: C₂₉H₄₁N₃O₃
• 分子量: 479.663
• InChiKey: YRTQVPKBNMSDJD-UHFFFAOYSA-N

物化性质

• 沸点：
  657.1±55.0 °C(predicted)
• 密度：
  1.129±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  56.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(4-{4-[4-(2-isopropoxyphenyl)-1-piperazinyl]-4-hydroxybutyl}benzoyl)piperidine 在 palladium dihydroxide 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 50.0 ℃ 、413.68 kPa 条件下， 反应 192.0h， 生成 1-[4-[4-[4-[2-(1-Methylethoxy)phenyl]-1-piperazinyl]butyl]benzoyl]piperidine
  参考文献：
  名称：

  Orally Active Benzamide Antipsychotic Agents with Affinity for Dopamine D₂, Serotonin 5-HT_1A, and Adrenergic α₁ Receptors

  摘要：

  New antipsychotic drugs are needed because current therapy is ineffective for many schizophrenics and because treatment is often accompanied by extrapyramidal symptoms and dyskinesias. This paper describes the design, synthesis, and evaluation of a series of related (aminomethyl)benzamides in assays predictive of antipsychotic activity in humans. These compounds had notable affinity for dopamine D-2, serotonin 5-HT1A, and alpha(1)-adrenergic receptors. The arylpiperazine 1-[3-[[4-[2-(1-methylethoxy)phenyl]-1-piperazinyl]methyl]benzoyl]piperidine (mazapertine, 6) was chosen because of its overall profile for evaluation in human clinical trials. The corresponding 4-arylpiperidine derivative 67 was also highly active indicating that the aniline nitrogen of 6 is not required for activity. Other particularly active structures include homopiperidine amide 14 and N-methylcyclohexylamide 31.

  DOI：

  10.1021/jm970164z
• 作为产物：
  描述：

  2-(1-methylethoxy)phenyl-1-piperazine 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium tetrahydroborate 、 N,N-二异丙基乙胺 、 sodium iodide 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 100.0 ℃ 、101.33 kPa 条件下， 反应 268.0h， 生成 1-(4-{4-[4-(2-isopropoxyphenyl)-1-piperazinyl]-4-hydroxybutyl}benzoyl)piperidine
  参考文献：
  名称：

  Orally Active Benzamide Antipsychotic Agents with Affinity for Dopamine D₂, Serotonin 5-HT_1A, and Adrenergic α₁ Receptors

  摘要：

  New antipsychotic drugs are needed because current therapy is ineffective for many schizophrenics and because treatment is often accompanied by extrapyramidal symptoms and dyskinesias. This paper describes the design, synthesis, and evaluation of a series of related (aminomethyl)benzamides in assays predictive of antipsychotic activity in humans. These compounds had notable affinity for dopamine D-2, serotonin 5-HT1A, and alpha(1)-adrenergic receptors. The arylpiperazine 1-[3-[[4-[2-(1-methylethoxy)phenyl]-1-piperazinyl]methyl]benzoyl]piperidine (mazapertine, 6) was chosen because of its overall profile for evaluation in human clinical trials. The corresponding 4-arylpiperidine derivative 67 was also highly active indicating that the aniline nitrogen of 6 is not required for activity. Other particularly active structures include homopiperidine amide 14 and N-methylcyclohexylamide 31.

  DOI：

  10.1021/jm970164z