cis-3-(3-methoxyphenyl)-5-<(methylmercapto)methyl>-N-n-propylpiperidin | 97000-33-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: cis-3-(3-methoxyphenyl)-5-<(methylmercapto)methyl>-N-n-propylpiperidin
• 英文别名: cis-3-(3-methoxyphenyl)-5-[(methylmercapto)methyl]-N-n-propylpiperidin
• CAS: 97000-33-4；97000-34-5
• 化学式: C₁₇H₂₇NO₃S
• 分子量: 325.472
• InChiKey: UBCDNPSUQOFPQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  cis-3-(3-methoxyphenyl)-5-<(methylmercapto)methyl>-N-n-propylpiperidin 在 氢溴酸 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 水 、 溶剂黄146 为溶剂， 反应 2.5h， 生成 cis-3-(3-hydroxyphenyl)-5-<(methylmercapto)methyl>-N-n-propylpiperidine
  参考文献：
  名称：

  Synthesis and dopamine autoreceptor activity of a 5-(methylmercapto)methyl-substituted derivative of(.+-.)-3-PPP [3-(3-hydroxyphenyl)-1-propylpiperidine]

  摘要：

  In an attempt to enhance the potency of the dopamine autoreceptor agonist 3-PPP, racemic cis-3-(3-hydroxyphenyl)-5-[(methylmercapto)methyl]-N-n-propylpiperidine has been prepared in a stereoselective synthesis. NMR studies of 3 show a diequatorial conformation for the 3- and 5-substituents, which gives compound 3 an intriguing overlap with the ergoline derivative pergolide. Pharmacological testing revealed that 3, which is a 5-(methylmercapto)methyl derivative of racemic 3-PPP does not show the anticipated potency increase as a dopamine autoreceptor agonist. In vitro (inhibition of tyrosine hydroxylation) 3 and 1 have similar potency, and the in vivo potency (inhibition of GBL accelerated dopamine synthesis) of 3 is inferior to that of 1.

  DOI：

  10.1021/jm00147a046
• 作为产物：
  描述：

  methyl 5-(3-methoxyphenyl)piperidine-3-carboxylate 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 反应 21.08h， 生成 cis-3-(3-methoxyphenyl)-5-<(methylmercapto)methyl>-N-n-propylpiperidin
  参考文献：
  名称：

  Synthesis and dopamine autoreceptor activity of a 5-(methylmercapto)methyl-substituted derivative of(.+-.)-3-PPP [3-(3-hydroxyphenyl)-1-propylpiperidine]

  摘要：

  In an attempt to enhance the potency of the dopamine autoreceptor agonist 3-PPP, racemic cis-3-(3-hydroxyphenyl)-5-[(methylmercapto)methyl]-N-n-propylpiperidine has been prepared in a stereoselective synthesis. NMR studies of 3 show a diequatorial conformation for the 3- and 5-substituents, which gives compound 3 an intriguing overlap with the ergoline derivative pergolide. Pharmacological testing revealed that 3, which is a 5-(methylmercapto)methyl derivative of racemic 3-PPP does not show the anticipated potency increase as a dopamine autoreceptor agonist. In vitro (inhibition of tyrosine hydroxylation) 3 and 1 have similar potency, and the in vivo potency (inhibition of GBL accelerated dopamine synthesis) of 3 is inferior to that of 1.

  DOI：

  10.1021/jm00147a046