1-[6,7-dimethoxy-1-(4-nitrophenyl)-3,4-dihydro-1H-isoquinolin-2-yl]-2-piperidin-1-ylethanone | 910108-75-7

• 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: 1-[6,7-dimethoxy-1-(4-nitrophenyl)-3,4-dihydro-1H-isoquinolin-2-yl]-2-piperidin-1-ylethanone
• CAS: 910108-75-7
• 化学式: C₂₄H₂₉N₃O₅
• 分子量: 439.511
• InChiKey: XREJKRJCFOAFLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  87.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[6,7-dimethoxy-1-(4-nitrophenyl)-3,4-dihydro-1H-isoquinolin-2-yl]-2-piperidin-1-ylethanone 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以42%的产率得到1-[1-(4-aminophenyl)-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：

  6,7-二甲氧基-1-(4-硝基-苯基)-1,2,3,4-四氢-异喹啉 在 potassium carbonate 、 三乙胺 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 3.0h， 生成 1-[6,7-dimethoxy-1-(4-nitrophenyl)-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

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.