N-(4-2-(3,4-二氢-1H-异喹啉-2-基)乙基苯基)-2-硝基苯甲酰胺 | 82924-82-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 中文名称: N-(4-2-(3,4-二氢-1H-异喹啉-2-基)乙基苯基)-2-硝基苯甲酰胺
• 英文名称: 6,7-Dimethoxy-2-[(4-nitrophenyl)acetyl]-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 1-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-2-(4-nitrophenyl)ethanone
• CAS: 82924-82-1
• 化学式: C₁₉H₂₀N₂O₅
• mdl: MFCD15411248
• 分子量: 356.378
• InChiKey: LOSARNASPVXQAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 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：

  N-(4-2-(3,4-二氢-1H-异喹啉-2-基)乙基苯基)-2-硝基苯甲酰胺 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 2-(4-aminophenyl)-1-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)ethanone
  参考文献：
  名称：

  Synthesis and Activity against Multidrug Resistance in Chinese Hamster Ovary Cells of New Acridone-4-carboxamides

  摘要：

  A number of tricyclic carboxamides have been synthesized and tested to evaluate their ability to reverse multidrug resistance in the (CHC)-C-R/5 cell line. Among them the acridone derivatives were the most potent, A key feature is the presence of a dimethoxybenzyl or phenethylamine cationic site, separated from the tricyclic lipophilic part by a carbamoylphenyl chain. Optimization led to compounds 2 orders of magnitude more active than the prototype inhibitors verapamil and amiodarone. On the basis of in vitro and in vivo activities, 9,10-dihydro-5-methoxy- 9-oxo-N-[4-[2-(1,2,3,4-tetrahydro-6,7-dimethoxyisoquinol-2-yl)ethyl]phenyl]-4-acridinecarboxamide (84) has been selected for further development.

  DOI：

  10.1021/jm00013a017
• 作为产物：
  描述：

  对硝基苯乙酸 在 氯化亚砜 、 碳酸氢钠 作用下， 以 丙酮 为溶剂， 反应 9.0h， 生成 N-(4-2-(3,4-二氢-1H-异喹啉-2-基)乙基苯基)-2-硝基苯甲酰胺
  参考文献：
  名称：

  Synthesis and Activity against Multidrug Resistance in Chinese Hamster Ovary Cells of New Acridone-4-carboxamides

  摘要：

  A number of tricyclic carboxamides have been synthesized and tested to evaluate their ability to reverse multidrug resistance in the (CHC)-C-R/5 cell line. Among them the acridone derivatives were the most potent, A key feature is the presence of a dimethoxybenzyl or phenethylamine cationic site, separated from the tricyclic lipophilic part by a carbamoylphenyl chain. Optimization led to compounds 2 orders of magnitude more active than the prototype inhibitors verapamil and amiodarone. On the basis of in vitro and in vivo activities, 9,10-dihydro-5-methoxy- 9-oxo-N-[4-[2-(1,2,3,4-tetrahydro-6,7-dimethoxyisoquinol-2-yl)ethyl]phenyl]-4-acridinecarboxamide (84) has been selected for further development.

  DOI：

  10.1021/jm00013a017

文献信息

• 2-amino (or hydroxy) phenethyl-1,2,3,4-tetrahydroisoquinolines as
  申请人：Pennwalt Corporation

  公开号：US04766131A1

  公开（公告）日：1988-08-23

  Analgesic 1,2,3,4-tetrahydroisoquinolines of the formula (1) ##STR1## wherein R.sub.1 and R.sub.2 respectively are hydrogen, hydroxy or alkoxy of 1 to 4 carbon atoms, R.sub.3 and R.sub.4 respectively are hydrogen or alkyl of 1 to 4 carbon atoms, and R.sub.5 is hydroxy, nitro or ##STR2## wherein R.sub.6 and R.sub.7 respectively are hydrogen, alkyl of 1 to 4 carbon atoms or RCO-- wherein R is hydrogen or alkyl of 1 to 4 carbon atoms; pharmaceutically acceptable addition salts thereof with non-toxic acids; analgesic compositions thereof in an inert, pharmaceutical carrier; and methods of preparation from corresponding R.sub.1, R.sub.2, R.sub.3 and R.sub.4 -substituted tetrahydroisoquinolines.

  镇痛剂1,2,3,4-四氢异喹啉的化学式（1）##STR1## 其中R.sub.1和R.sub.2分别为氢，羟基或1到4个碳原子的烷氧基，R.sub.3和R.sub.4分别为氢或1到4个碳原子的烷基，R.sub.5为羟基，硝基或##STR2## 其中R.sub.6和R.sub.7分别为氢，1到4个碳原子的烷基或RCO--，其中R为氢或1到4个碳原子的烷基; 与无毒酸的药学上可接受的加成盐; 以惰性药物载体为基础的其镇痛组合物; 以及从相应的R.sub.1，R.sub.2，R.sub.3和R.sub.4-取代的四氢异喹啉制备的方法。
• N-(amino(or hydroxy) phenethyl)-1,2,3,4-tetrahydroisoquinolines, precursors thereof, and methods of preparation
  申请人：PENNWALT CORPORATION

  公开号：EP0051190A2

  公开（公告）日：1982-05-12

  Analgesic 1,2,3,4 tetrahydroisoquinolines of the formula wherein R, and R2 respectively are hydrogen, hydroxy or alkoxy of 1 to 4 carbon atoms, R3 and R4 respectively are hydrogen or alkyl of 1 to 4 carbon atoms, and R5 is hydroxy, nitro or wherein Rs and R7 respectively are hydrogen, alkyl of 1 to 4 carbon atoms or RCO- wherein R is hydrogen or alkyl of 1 to 4 carbon atoms; pharmaceutically acceptable addition salts thereof with non-toxic acids; analgesic compositions thereof in an inert, pharmaceutical carrier; and methods of preparation from corresponding R1, R2, R3 and R4-substituted tetrahydroisoquinolines.

  式中的 1，2，3，4 四氢异喹啉类镇痛剂 其中 R 和 R2 分别为氢、羟基或 1 至 4 个碳原子的烷氧基，R3 和 R4 分别为氢或 1 至 4 个碳原子的烷基，R5 为羟基、硝基或 RCO-。 其中 Rs 和 R7 分别为氢、1 至 4 个碳原子的烷基或 RCO-，其中 R 为氢或 1 至 4 个碳原子的烷基；其与无毒酸的药学上可接受的加成盐；其在惰性药物载体中的镇痛组合物；以及由相应的 R1、R2、R3 和 R4 取代的四氢异喹啉的制备方法。
• DAVIDSON, THOMAS A.;GRIFFITH, RONALD C.
  作者：DAVIDSON, THOMAS A.、GRIFFITH, RONALD C.

  DOI：——

  日期：——
• US4766131A
  申请人：——

  公开号：US4766131A

  公开（公告）日：1988-08-23
• Synthesis and Activity against Multidrug Resistance in Chinese Hamster Ovary Cells of New Acridone-4-carboxamides
  作者：Nerina Dodic、Bernard Dumaitre、Alain Daugan、Pascal Pianetti

  DOI：10.1021/jm00013a017

  日期：1995.6

  A number of tricyclic carboxamides have been synthesized and tested to evaluate their ability to reverse multidrug resistance in the (CHC)-C-R/5 cell line. Among them the acridone derivatives were the most potent, A key feature is the presence of a dimethoxybenzyl or phenethylamine cationic site, separated from the tricyclic lipophilic part by a carbamoylphenyl chain. Optimization led to compounds 2 orders of magnitude more active than the prototype inhibitors verapamil and amiodarone. On the basis of in vitro and in vivo activities, 9,10-dihydro-5-methoxy- 9-oxo-N-[4-[2-(1,2,3,4-tetrahydro-6,7-dimethoxyisoquinol-2-yl)ethyl]phenyl]-4-acridinecarboxamide (84) has been selected for further development.