4-benzyl-2-(((ethoxycarbonyl)amino)methyl)morpholine | 146944-29-8

• 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: 4-benzyl-2-(((ethoxycarbonyl)amino)methyl)morpholine
• 英文别名: ethyl N-[(4-benzylmorpholin-2-yl)methyl]carbamate
• CAS: 146944-29-8
• 化学式: C₁₅H₂₂N₂O₃
• 分子量: 278.351
• InChiKey: SSTXWDRBGBVEBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  50.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-benzyl-2-(((ethoxycarbonyl)amino)methyl)morpholine 在 palladium on activated charcoal 一水合肼 作用下， 以 异丙醇 为溶剂， 反应 1.5h， 以87%的产率得到乙基(2-吗啉基甲基)氨基甲酸酯
  参考文献：
  名称：

  Quinolone antimicrobial agents substituted with morpholines at the 7-position. Syntheses and structure-activity relationships

  摘要：

  A series of novel 7-substituted 1-cyclopropyl-6,8-difluoro- 1,4-dihydro-4-oxo-3-quinolinecarboxylic acids have been prepared and tested for antibacterial activities and for convulsive activities in combination with nonsteroidal antiinflammatory drug. Structure-activity relationships revealed that 7-(2-(aminomethyl)morpholino) derivative 28 had a better Gram-positive activity than the reference quinolones, such as ciprofloxacin, norfloxacin, and ofloxacin. Its Gram-negative activity was equipotent with those of norfloxacin and ofloxacin but was inferior to that of ciprofloxacin. In mouse systemic infection models, 28 showed an excellent therapeutic efficacy which might result from the potent antibacterial activity and suitable physicochemical properties. Convulsive activities of 7-morpholino derivatives in combination with nonsteroidal antiinflammatory drug fenbufen or its metabolite biphenylacetic acid markedly diminished as compared to those of 7-piperazino derivatives in the electrophysiological, biochemical, and behavioral experiments. These results suggest that 28 (Y-26611) is a novel quinolone with reduced neurotoxic excitatory adverse reaction.

  DOI：

  10.1021/jm00062a007
• 作为产物：
  描述：

  4-苄基-2-吗啉乙腈 在 sodium hypochlorite 、 硫酸 作用下， 反应 6.0h， 生成 4-benzyl-2-(((ethoxycarbonyl)amino)methyl)morpholine
  参考文献：
  名称：

  Quinolone antimicrobial agents substituted with morpholines at the 7-position. Syntheses and structure-activity relationships

  摘要：

  A series of novel 7-substituted 1-cyclopropyl-6,8-difluoro- 1,4-dihydro-4-oxo-3-quinolinecarboxylic acids have been prepared and tested for antibacterial activities and for convulsive activities in combination with nonsteroidal antiinflammatory drug. Structure-activity relationships revealed that 7-(2-(aminomethyl)morpholino) derivative 28 had a better Gram-positive activity than the reference quinolones, such as ciprofloxacin, norfloxacin, and ofloxacin. Its Gram-negative activity was equipotent with those of norfloxacin and ofloxacin but was inferior to that of ciprofloxacin. In mouse systemic infection models, 28 showed an excellent therapeutic efficacy which might result from the potent antibacterial activity and suitable physicochemical properties. Convulsive activities of 7-morpholino derivatives in combination with nonsteroidal antiinflammatory drug fenbufen or its metabolite biphenylacetic acid markedly diminished as compared to those of 7-piperazino derivatives in the electrophysiological, biochemical, and behavioral experiments. These results suggest that 28 (Y-26611) is a novel quinolone with reduced neurotoxic excitatory adverse reaction.

  DOI：

  10.1021/jm00062a007