1-carbethoxy-4-[2-(1-methylethoxy)phenyl]piperidine | 148583-62-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-carbethoxy-4-[2-(1-methylethoxy)phenyl]piperidine
• 英文别名: Carbethoxy-4-[2-(1-methylethoxy)phenyl]piperidine；ethyl 4-(2-propan-2-yloxyphenyl)piperidine-1-carboxylate
• CAS: 148583-62-4
• 化学式: C₁₇H₂₅NO₃
• 分子量: 291.39
• InChiKey: VLCMFIDDZVBXRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-carbethoxy-4-[2-(1-methylethoxy)phenyl]piperidine 在 sodium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 96.0h， 生成 哌啶,4-[2-(1-甲基乙氧基)苯基]-
  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：

  N-乙氧羰基-4-哌啶酮 在 palladium on activated charcoal 盐酸 、 氢气 、 1,2-二溴乙烷 作用下， 以 甲醇 、 乙醚 为溶剂， 22.0 ℃ 、382.66 kPa 条件下， 反应 74.0h， 生成 1-carbethoxy-4-[2-(1-methylethoxy)phenyl]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

文献信息

• [EN] NOVEL 4-ARYLPIPERAZINES AND 4-ARYLPIPERIDINES
  申请人：McNEILAB, INC.

  公开号：WO1993004684A1

  公开（公告）日：1993-03-18

  (EN) Compounds of the general formula (I) are disclosed as novel antipsychotic agents.(FR) Cette invention concerne des composés de formule (I) utiles comme nouveaux agents antipsychotiques.

  (I)式化合物被披露为新型抗精神病药物。(FR)该发明涉及公式（I）的化合物，作为新型抗精神病药物。
• 4-arylpiperazines and 4-arylpiperidines
  申请人：McNeilab, Inc.

  公开号：US05569659A1

  公开（公告）日：1996-10-29

  Compounds of the general formula I: ##STR1## are disclosed as novel antipsychotic agents.

  公式为I的化合物：##STR1## 被披露为新型抗精神病药物。
• N-OXIDES OF 4-ARYLPIPERAZINES AND 4-ARYLPIPERIDINES AS ANTIPSYCHOTIC DRUGS
  申请人：ORTHO PHARMACEUTICAL CORPORATION

  公开号：EP0736009B1

  公开（公告）日：2002-09-11
• NOVEL 4-ARYLPIPERAZINES AND 4-ARYLPIPERIDINES
  申请人：MCNEILAB, INC.

  公开号：EP0562049A1

  公开（公告）日：1993-09-29
• [EN] N-OXIDES OF 4-ARYLPIPERAZINES AND 4-ARYLPIPERIDINES AS ANTIPSYCHOTIC DRUGS<br/>[FR] N-OXYDES DE 4-ARYLEPIPERAZINES ET 4-ARYLPIPERIDINES UTILISES COMME MEDICAMENTS NEUROLEPTIQUES
  申请人：ORTHO PHARMACEUTICAL CORPORATION

  公开号：WO1995017385A1

  公开（公告）日：1995-06-29

  (EN) Compounds of general formula (I) are disclosed as novel antipsychotic agents.(FR) Composés de la formule générale (I) utilisés comme nouveaux agents neuroleptiques.