3-<3-<(dimethylcarbamoyl)oxy>phenyl>-N-propylpiperidine | 110174-87-3

• 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: 3-<3-<(dimethylcarbamoyl)oxy>phenyl>-N-propylpiperidine
• 英文别名: [3-(1-propylpiperidin-3-yl)phenyl] N,N-dimethylcarbamate
• CAS: 110174-87-3
• 化学式: C₁₇H₂₆N₂O₂
• 分子量: 290.406
• InChiKey: KCECUNPSORVJQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 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：
  32.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-n-Propyl-3-(3-hydroxyphenyl)piperidine hydrochloride 、 二甲氨基甲酰氯 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 3-<3-<(dimethylcarbamoyl)oxy>phenyl>-N-propylpiperidine
  参考文献：
  名称：

  Carbamate ester derivatives as potential prodrugs of the presynaptic dopamine autoreceptor agonist (-)-3-(3-hydroxyphenyl)-N-propylpiperidine

  摘要：

  Twenty derivatives bearing substituents on the phenolic function of (-)-3-(3-hydroxyphenyl)-N-propylpiperidine [(-)-3-PPP] were synthesized and tested as prodrugs. The carbamate ester derivatives were found to be the most suitable prodrugs, and especially the 4-isopropylphenylcarbamate 20 was capable of escaping the first-pass metabolism and still generating high plasma levels of the parent compound. Four hours after an oral dose of 100 mumol/kg to rats, a plasma level of 2400 nmol/L of (-)-3-PPP was detected by an HPLC method. This was 90 times the level reached after 4 h (27 nmol/L) when (-)-3-PPP itself was given orally at the same dose.

  DOI：

  10.1021/jm00394a014

文献信息

• Piperidine derivatives, processes for their preparation and pharmaceutical preparation containing them
  申请人：Carlsson, Per Arvid Emil

  公开号：EP0097628B1

  公开（公告）日：1990-09-19
• Carbamate ester derivatives as potential prodrugs of the presynaptic dopamine autoreceptor agonist (-)-3-(3-hydroxyphenyl)-N-propylpiperidine
  作者：Seth Olov Thorberg、Stefan Berg、Jan Lundstroem、Bodil Pettersson、Agneta Wijkstroem、Domingo Sanchez、Per Lindberg、J. Lars G. Nilsson

  DOI：10.1021/jm00394a014

  日期：1987.11

  Twenty derivatives bearing substituents on the phenolic function of (-)-3-(3-hydroxyphenyl)-N-propylpiperidine [(-)-3-PPP] were synthesized and tested as prodrugs. The carbamate ester derivatives were found to be the most suitable prodrugs, and especially the 4-isopropylphenylcarbamate 20 was capable of escaping the first-pass metabolism and still generating high plasma levels of the parent compound. Four hours after an oral dose of 100 mumol/kg to rats, a plasma level of 2400 nmol/L of (-)-3-PPP was detected by an HPLC method. This was 90 times the level reached after 4 h (27 nmol/L) when (-)-3-PPP itself was given orally at the same dose.