N-benzyl-N-methyl-(4-nitrophenoxy)acetylamide | 143666-76-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-benzyl-N-methyl-(4-nitrophenoxy)acetylamide
• 英文别名: N-benzyl-N-methyl-2-(4-nitrophenoxy)acetamide
• CAS: 143666-76-6
• 化学式: C₁₆H₁₆N₂O₄
• 分子量: 300.314
• InChiKey: FHCASHGVHQFHML-UHFFFAOYSA-N

物化性质

• 沸点：
  502.6±40.0 °C(Predicted)
• 密度：
  1.251±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  75.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-benzyl-N-methyl-(4-nitrophenoxy)acetylamide 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 60.0 ℃ 、101.33 kPa 条件下， 反应 4.0h， 生成 4-[2-[Benzyl(methyl)amino]ethoxy]aniline
  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：

  4-硝基苯氧乙酸 在 氯化亚砜 、 碳酸氢钠 作用下， 以 丙酮 为溶剂， 反应 7.0h， 生成 N-benzyl-N-methyl-(4-nitrophenoxy)acetylamide
  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

• Room-Temperature Debenzylation of <i>N</i>-Benzylcarboxamides by<i> N</i>-Bromosuccinimide
  作者：Ke Ding、Liping Kuang、Jing Zhou、Sheng Chen

  DOI：10.1055/s-2007-990795

  日期：2007.10

  A simple and highly efficient method has been developed with which to cleave the N-benzyl group on N-mono- or di­substituted carboxamides using N-bromosuccinimide (NBS) at room temperature. All the 31 substrates examined showed moderate to excellent deprotection yields. Our study also indicated that the debenzylation may involve an oxygen/light initiated free radical mechanism.

  开发了一种简单且高效的方法，可以在室温下使用N-溴琥珀酰亚胺（NBS）去除N-单取代或双取代羧酰胺上的N-苄基基团。所有31种被检验的底物表现出中等到优秀的去保护产率。我们的研究还表明，去苄基化可能涉及氧/光引发的自由基机制。
• Certain isoquinoline derivatives having anti-tumor properties
  申请人：Laboratoires Glaxo SA

  公开号：US05663179A1

  公开（公告）日：1997-09-02

  Compounds are described of general formula (I) ##STR1## and salts and solvates thereof, including physiologically acceptable salts and solvates thereof, in which: Z represents either Het, ##STR2## Het represents an optionally substituted bicyclic or tricyclic ring selected from acricine isoquinolin-1-yl, isoquinolin-3-yl, The novel compounds of formula (I) can sensitize multi-drug resistant cancer cells to chemotherapeutic agents and may be formulated for use in therapy, particularly to improve or increase the efficacy of an anti-tumour drug.

  化合物的一般式(I)描述如下：##STR1##及其盐和溶剂化物，包括生理上可接受的盐和溶剂化物，其中：Z代表Het或##STR2## Het代表可选取自acricine isoquinolin-1-yl、isoquinolin-3-yl的含取代的双环或三环环状结构。式(I)的新型化合物能够增强多药耐药癌细胞对化疗药物的敏感性，并可制成治疗用药物，特别是为了改善或增强抗肿瘤药物的功效。
• EP0494623A1
  申请人：——

  公开号：EP0494623A1

  公开（公告）日：1992-07-15
• ACRIDINE DERIVATIVES
  申请人：LABORATOIRES GLAXO SA

  公开号：EP0569380A1

  公开（公告）日：1993-11-18
• ANILIDE DERIVATIVES
  申请人：LABORATOIRES GLAXO SA

  公开号：EP0649410A1

  公开（公告）日：1995-04-26