6,7-Dimethoxy-2-benzoyl-1-(2-naphthylmethyl)-1-cyano-1,2-dihydroisochinolin | 112504-24-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 6,7-Dimethoxy-2-benzoyl-1-(2-naphthylmethyl)-1-cyano-1,2-dihydroisochinolin
• 英文别名: 2-Benzoyl-6,7-dimethoxy-1-(naphthalen-2-ylmethyl)isoquinoline-1-carbonitrile
• CAS: 112504-24-2
• 化学式: C₃₀H₂₄N₂O₃
• 分子量: 460.532
• InChiKey: XQWAEALDNQUPBM-UHFFFAOYSA-N

物化性质

• 熔点：
  162 °C(Solv: ethanol (64-17-5))
• 沸点：
  697.2±55.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6,7-Dimethoxy-2-benzoyl-1-(2-naphthylmethyl)-1-cyano-1,2-dihydroisochinolin 在 sodium hydroxide 、 sodium tetrahydroborate 作用下， 以 甲醇 、 乙醇 、 乙腈 为溶剂， 反应 2.25h， 生成 6,7-dimethoxy-2-methyl-1-(naphthalen-2-ylmethyl)-1,2,3,4-tetrahydroisoquinoline
  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
• 作为产物：
  描述：

  6,7-二甲氧基异喹啉 在 三氯化铝 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 6,7-Dimethoxy-2-benzoyl-1-(2-naphthylmethyl)-1-cyano-1,2-dihydroisochinolin
  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

• Dihydroisochinolinumlagerung, 37. Mitt. Synthese von Isochinoliniumsalzen mit sperrigen C-1-Substituenten als Vorstufen für 1,2-Dihydroisochinoline
  作者：Joachim Knabe、Franz-Josef Grünewald

  DOI：10.1002/ardp.19873200405

  日期：——

  Durch Alkylierung der Reissert‐Verbindung 1 werden die Verbindungen 2a‐2d erhalten. Diese ergeben nach Verseifung die Isochinoline 3a‐3d, die mit Methyliodid zu den Iminiumiodiden 4a‐4d umgesetzt werden.

  Reissert 化合物 1 烷基化得到化合物 2a-2d。皂化后，这些得到异喹啉 3a-3d，其与甲基碘反应形成亚胺碘化物 4a-4d。
• KNABE J.; GRUNEWALD F. -J., ARCH. PHARM., 320,(1987) N 4, 303-308
  作者：KNABE J.、 GRUNEWALD F. -J.

  DOI：——

  日期：——