2-(chloroacetyl)-1-(4-chlorophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline | 910108-64-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 2-(chloroacetyl)-1-(4-chlorophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 2-chloro-1-[1-(4-chlorophenyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]ethanone
• CAS: 910108-64-4
• 化学式: C₁₉H₁₉Cl₂NO₃
• 分子量: 380.271
• InChiKey: VLOJLECUZADIJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  哌啶 、 2-(chloroacetyl)-1-(4-chlorophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 在 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 1.5h， 以55%的产率得到1-[1-(4-chlorophenyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-2-piperidin-1-ylethanone
  参考文献：
  名称：

  Novel Potent Anticonvulsant Agent Containing a Tetrahydroisoquinoline Skeleton

  摘要：

  In our studies on the development of new anticonvulsants, we planned the synthesis of N-substituted 1,2,3,4-tetrahydroisoquinolines to explore the structure-activity relationships. All derivatives were evaluated against audiogenic seizures in DBA/2 mice, and the 1-(4'-bromophenyl)-6,7-dimethoxy-2-(piperidin-1-ylacetyl)derivative (26) showed the highest activity with a potency comparable to that of talampanel, the only noncompetitive alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) antagonist in clinical trials as an anticonvulsant agent. Electrophysiological experiments indicated that 26 acts as noncompetitive AMPA receptor modulator.

  DOI：

  10.1021/jm060411b
• 作为产物：
  描述：

  1-(4-氯苯基)-6,7-二甲氧基-1,2,3,4-四氢异喹啉 、 氯乙酰氯 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 1.5h， 以64%的产率得到2-(chloroacetyl)-1-(4-chlorophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Novel Potent Anticonvulsant Agent Containing a Tetrahydroisoquinoline Skeleton

  摘要：

  In our studies on the development of new anticonvulsants, we planned the synthesis of N-substituted 1,2,3,4-tetrahydroisoquinolines to explore the structure-activity relationships. All derivatives were evaluated against audiogenic seizures in DBA/2 mice, and the 1-(4'-bromophenyl)-6,7-dimethoxy-2-(piperidin-1-ylacetyl)derivative (26) showed the highest activity with a potency comparable to that of talampanel, the only noncompetitive alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) antagonist in clinical trials as an anticonvulsant agent. Electrophysiological experiments indicated that 26 acts as noncompetitive AMPA receptor modulator.

  DOI：

  10.1021/jm060411b

文献信息

• Novel Potent Anticonvulsant Agent Containing a Tetrahydroisoquinoline Skeleton
  作者：Rosaria Gitto、Roberta Caruso、Benedetta Pagano、Laura De Luca、Rita Citraro、Emilio Russo、Giovambattista De Sarro、Alba Chimirri

  DOI：10.1021/jm060411b

  日期：2006.9.1

  In our studies on the development of new anticonvulsants, we planned the synthesis of N-substituted 1,2,3,4-tetrahydroisoquinolines to explore the structure-activity relationships. All derivatives were evaluated against audiogenic seizures in DBA/2 mice, and the 1-(4'-bromophenyl)-6,7-dimethoxy-2-(piperidin-1-ylacetyl)derivative (26) showed the highest activity with a potency comparable to that of talampanel, the only noncompetitive alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) antagonist in clinical trials as an anticonvulsant agent. Electrophysiological experiments indicated that 26 acts as noncompetitive AMPA receptor modulator.