2-chloroacetyl-6,7-dimethoxy-1-(4-nitro-phenyl)-1,2,3,4-tetrahydro-isoquinoline | 66040-43-5

• 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-6,7-dimethoxy-1-(4-nitro-phenyl)-1,2,3,4-tetrahydro-isoquinoline
• 英文别名: 2-chloro-1-[6,7-dimethoxy-1-(4-nitrophenyl)-3,4-dihydro-1H-isoquinolin-2-yl]ethanone
• CAS: 66040-43-5
• 化学式: C₁₉H₁₉ClN₂O₅
• 分子量: 390.823
• InChiKey: MTMAOAABDQIPBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 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：
  84.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-chloroacetyl-6,7-dimethoxy-1-(4-nitro-phenyl)-1,2,3,4-tetrahydro-isoquinoline 在 palladium on activated charcoal 氢气 、 potassium carbonate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 2.5h， 生成 1-[1-(4-aminophenyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-2-morpholin-4-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：

  2-氯-N-(2-(3,4-二甲氧基苯基)乙基)乙酰胺 、 对硝基苯甲醛 在 硫酸 、 溶剂黄146 作用下， 反应 240.0h， 以88%的产率得到2-chloroacetyl-6,7-dimethoxy-1-(4-nitro-phenyl)-1,2,3,4-tetrahydro-isoquinoline
  参考文献：
  名称：

  Improved Methods for the Synthesis of N-Acyltetrahydroisoquinolines

  摘要：

  One-pot procedures for the synthesis of N-acyltetrahydroisoquinolines have been developed from 2-phenylethylamines, acyl chlorides or carboxylic acids and aldehydes.

  DOI：

  10.1080/00397919208021138

文献信息

• MOLLLOV N. M.; BEHKOB A. P., NAUCH. TR. PLOVDIV. YH-T. XIMIYA, 1978(1979), 16, HO 3, 191-214
  作者：MOLLLOV N. M.、 BEHKOB A. P.

  DOI：——

  日期：——
• Venkov A. P., Lukanov L. K., Synth. Commun., 22 (1992) N 22, S 3235-3242
  作者：Venkov A. P., Lukanov L. K.

  DOI：——

  日期：——
• 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.
• Improved Methods for the Synthesis of N-Acyltetrahydroisoquinolines
  作者：A. P. Venkov、L. K. Lukanov

  DOI：10.1080/00397919208021138

  日期：1992.12

  One-pot procedures for the synthesis of N-acyltetrahydroisoquinolines have been developed from 2-phenylethylamines, acyl chlorides or carboxylic acids and aldehydes.