(+/-)-N,N-Dimethyl-6,7,3',4'-tetramethoxyphenylethyl-1,2,3,4-tetrahydroisoquinolinium iodide | 105578-49-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 苯乙基异喹啉生物碱
• 英文名称: (+/-)-N,N-Dimethyl-6,7,3',4'-tetramethoxyphenylethyl-1,2,3,4-tetrahydroisoquinolinium iodide
• 英文别名: Homolaudanosin-methojodid；1-[2-(3,4-dimethoxyphenyl)ethyl]-6,7-dimethoxy-2,2-dimethyl-3,4-dihydro-1H-isoquinolin-2-ium;iodide
• CAS: 105578-49-2
• 化学式: C₂₃H₃₂NO₄*I
• 分子量: 513.416
• InChiKey: OVELEZMOERRWJH-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.03
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  homolaudanosine 、 碘甲烷 以 乙腈 为溶剂， 反应 4.0h， 以78%的产率得到(+/-)-N,N-Dimethyl-6,7,3',4'-tetramethoxyphenylethyl-1,2,3,4-tetrahydroisoquinolinium iodide
  参考文献：
  名称：

  Synthesis and Radioligand Binding Studies of Methoxylated 1,2,3,4-Tetrahydroisoquinolinium Derivatives as Ligands of the Apamin-Sensitive Ca²⁺-Activated K⁺ Channels

  摘要：

  Several methoxylated 1,2,3,4-tetrahydroisoquinoliniums derived from N-methyl-laudanosine and N-methyl-noscapine were synthesized and evaluated for their affinity for apamin-sensitive binding sites. The quaternary ammonium derivatives have a higher affinity with regard to the tertiary amines. 6,7-Dimethoxy analogues possess a higher affinity than the 6,8- and 7,8- dimethoxy isomers. A 3,4-dimethoxybenzyl or a 2-naphthylmethyl moiety in C-1 position are more favorable than a 3,4-dimethoxyphenethyl group. Smaller groups such as propyl or isobutyl are unfavorable. In 6,7-dimethoxy analogues, increasing the size and lipophilicity with a naphthyl group in the C-1 position leads to a slight increase of affinity, while the same group in the 6,7,8- trimethoxy series is less favorable. The 6,7,8- trimethoxy derivative 3f is the first tertiary amine in the series to possess an affinity close to that of N-methyl-laudanosine and N-methyl-noscapine. Moreover, electrophysiological studies show that the most effective compound 4f blocks the apamin-sensitive afterhyperpolarization in rat dopaminergic neurons.

  DOI：

  10.1021/jm0607395

文献信息

• Veznik, Frantisek; Taborska, Eva; Sedmera, Petr, Collection of Czechoslovak Chemical Communications, 1986, vol. 51, # 8, p. 1752 - 1763
  作者：Veznik, Frantisek、Taborska, Eva、Sedmera, Petr、Dolejs, Ladislav、Slavik, Jiri

  DOI：——

  日期：——
• Synthesis and Radioligand Binding Studies of Methoxylated 1,2,3,4-Tetrahydroisoquinolinium Derivatives as Ligands of the Apamin-Sensitive Ca²⁺-Activated K⁺ Channels
  作者：Amaury Graulich、Jacqueline Scuvée-Moreau、Livia Alleva、Cédric Lamy、Olivier Waroux、Vincent Seutin、Jean-François Liégeois

  DOI：10.1021/jm0607395

  日期：2006.11.30

  Several methoxylated 1,2,3,4-tetrahydroisoquinoliniums derived from N-methyl-laudanosine and N-methyl-noscapine were synthesized and evaluated for their affinity for apamin-sensitive binding sites. The quaternary ammonium derivatives have a higher affinity with regard to the tertiary amines. 6,7-Dimethoxy analogues possess a higher affinity than the 6,8- and 7,8- dimethoxy isomers. A 3,4-dimethoxybenzyl or a 2-naphthylmethyl moiety in C-1 position are more favorable than a 3,4-dimethoxyphenethyl group. Smaller groups such as propyl or isobutyl are unfavorable. In 6,7-dimethoxy analogues, increasing the size and lipophilicity with a naphthyl group in the C-1 position leads to a slight increase of affinity, while the same group in the 6,7,8- trimethoxy series is less favorable. The 6,7,8- trimethoxy derivative 3f is the first tertiary amine in the series to possess an affinity close to that of N-methyl-laudanosine and N-methyl-noscapine. Moreover, electrophysiological studies show that the most effective compound 4f blocks the apamin-sensitive afterhyperpolarization in rat dopaminergic neurons.