tert-butyl 4-[(1RS)-1-(3,4-dichlorophenyl)-2-(ethylsulfanyl)ethyl]piperidine-1-carboxylate | 1207439-04-0

• 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: tert-butyl 4-[(1RS)-1-(3,4-dichlorophenyl)-2-(ethylsulfanyl)ethyl]piperidine-1-carboxylate
• CAS: 1207439-04-0
• 化学式: C₂₀H₂₉Cl₂NO₂S
• 分子量: 418.428
• InChiKey: HAMDAWSLUPKFKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.48
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-[(1RS)-1-(3,4-dichlorophenyl)-2-(ethylsulfanyl)ethyl]piperidine-1-carboxylate 在 盐酸 、 乙醇 作用下， 反应 0.25h， 以70%的产率得到4-[(1RS)-1-(3,4-dichlorophenyl)-2-(ethylsulfanyl)ethyl]piperidine monohydrochloride
  参考文献：
  名称：

  Novel triple reuptake inhibitors with low risk of CAD associated liabilities: Design, synthesis and biological activities of 4-[(1S)-1-(3,4-dichlorophenyl)-2-methoxyethyl]piperidine and related compounds

  摘要：

  A novel triple reuptake inhibitor with low potential of liabilities associated with cationic amphiphilic drug (CAD) was identified following an analysis of existing drugs. Low molecular weight (MW < ca. 300), low aromatic ring count (number = 1) and reduced lipophilicity (ClogP < 3.5) were hypothesized to be key factors to avoid the CAD associated liabilities (CYP2D6 inhibition, hERG inhibition and phospholipidosis). Based on the hypothesis, a series of piperidine compounds was designed with consideration of the common characteristic features of CNS drugs. Optimization of the side chain by adjusting overall lipophilicity suggested that incorporation of a methoxymethyl group could provide compounds with a balance of both potent reuptake inhibition and low liability potential. Compound (S)-3a showed a potent antidepressant-like effect in the mice tail suspension test (MED = 10 mg/kg, p.o.), proportional monoamine transporter occupancies and enhancement of monoamine concentrations in mouse prefrontal cortex. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.025
• 作为产物：
  描述：

  tert-butyl 4-{(1RS)-1-(3,4-dichlorophenyl)-2-[(methylsulfonyl)oxy]ethyl}piperidine-1-carboxylate 在 水 、 sodium hydride 、 sodium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 丙酮 、 mineral oil 为溶剂， 反应 22.17h， 生成 tert-butyl 4-[(1RS)-1-(3,4-dichlorophenyl)-2-(ethylsulfanyl)ethyl]piperidine-1-carboxylate
  参考文献：
  名称：

  Novel triple reuptake inhibitors with low risk of CAD associated liabilities: Design, synthesis and biological activities of 4-[(1S)-1-(3,4-dichlorophenyl)-2-methoxyethyl]piperidine and related compounds

  摘要：

  A novel triple reuptake inhibitor with low potential of liabilities associated with cationic amphiphilic drug (CAD) was identified following an analysis of existing drugs. Low molecular weight (MW < ca. 300), low aromatic ring count (number = 1) and reduced lipophilicity (ClogP < 3.5) were hypothesized to be key factors to avoid the CAD associated liabilities (CYP2D6 inhibition, hERG inhibition and phospholipidosis). Based on the hypothesis, a series of piperidine compounds was designed with consideration of the common characteristic features of CNS drugs. Optimization of the side chain by adjusting overall lipophilicity suggested that incorporation of a methoxymethyl group could provide compounds with a balance of both potent reuptake inhibition and low liability potential. Compound (S)-3a showed a potent antidepressant-like effect in the mice tail suspension test (MED = 10 mg/kg, p.o.), proportional monoamine transporter occupancies and enhancement of monoamine concentrations in mouse prefrontal cortex. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.025