3-carboxy-1,1-dimethyl-piperidinium; chloride | 62581-21-9

• 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-carboxy-1,1-dimethyl-piperidinium; chloride
• 英文别名: 3-Carboxy-1,1-dimethyl-piperidinium; Chlorid；1,1-Dimethylpiperidin-1-ium-3-carboxylate;hydrochloride
• CAS: 62581-21-9
• 化学式: C₈H₁₆NO₂*Cl
• 分子量: 193.674
• InChiKey: LXZKZZTXUVBBMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.44
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-哌啶甲酸 、 碘甲烷 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以84%的产率得到3-carboxy-1,1-dimethyl-piperidinium; chloride
  参考文献：
  名称：

  Synthesis and biological evaluation of cyclic analogs of l-carnitine as potential agents in the treatment of myocardial ischemia

  摘要：

  A series of cyclic rigid analogues of l-carnitine has been synthesized and examined for activity as substrates for the carnitine-acylcarnitine translocase, the enzyme that mediates transport of fatty acids into the mitochondria. Synthetic steps to seven of these analogues are described in this paper. Bioassay of these compounds is conducted in a preparation of isolated heart mitochondria that have been previously loaded with [14C]-l-carnitine. Efflux of radioactivity from the mitochondria is then monitored in the presence of the compound being evaluated in order to assess the amount of enzyme activity initiated. The palmityl ester of l-N,N-dimethyl-trans-2-carboxy-4-hydroxypyrrolidinium chloride elicited a 13.63 and 63.07% efflux of [14C]-l-carnitine at concentrations of 3 and 50 mM, respectively. This represents the first instance in which a nonnaturally occurring analogue of l-carnitine has been shown to undergo transport via this mitochondrial translocase, suggesting the possibility that cyclic carnitine analogues may find utility as agents in the treatment of myocardial ischemia.

  DOI：

  10.1021/jm00155a045

文献信息

• Synthesis and biological evaluation of cyclic analogs of l-carnitine as potential agents in the treatment of myocardial ischemia
  作者：Patrick M. Woster、Wallace J. Murray

  DOI：10.1021/jm00155a045

  日期：1986.5

  A series of cyclic rigid analogues of l-carnitine has been synthesized and examined for activity as substrates for the carnitine-acylcarnitine translocase, the enzyme that mediates transport of fatty acids into the mitochondria. Synthetic steps to seven of these analogues are described in this paper. Bioassay of these compounds is conducted in a preparation of isolated heart mitochondria that have been previously loaded with [14C]-l-carnitine. Efflux of radioactivity from the mitochondria is then monitored in the presence of the compound being evaluated in order to assess the amount of enzyme activity initiated. The palmityl ester of l-N,N-dimethyl-trans-2-carboxy-4-hydroxypyrrolidinium chloride elicited a 13.63 and 63.07% efflux of [14C]-l-carnitine at concentrations of 3 and 50 mM, respectively. This represents the first instance in which a nonnaturally occurring analogue of l-carnitine has been shown to undergo transport via this mitochondrial translocase, suggesting the possibility that cyclic carnitine analogues may find utility as agents in the treatment of myocardial ischemia.