[2-(Benzylamino)-2-oxo-1-phenylethyl] methanesulfonate | 188025-29-8

• 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: [2-(Benzylamino)-2-oxo-1-phenylethyl] methanesulfonate
• CAS: 188025-29-8
• 化学式: C₁₆H₁₇NO₄S
• 分子量: 319.381
• InChiKey: YYTZDAPHUVLWOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [2-(Benzylamino)-2-oxo-1-phenylethyl] methanesulfonate 在 四丁基氟化铵 作用下， 以 苯 为溶剂， 反应 0.5h， 以10%的产率得到N-benzyl-2-fluoro-2-phenylacetamide
  参考文献：
  名称：

  The anticonvulsant activities of functionalized N-benzyl 2-acetamidoacetamides. The importance of the 2-acetamido substituent

  摘要：

  Recent studies have demonstrated that substituted N-benzyl 2-acetamidoacetamides provide significant protection against maximal electroshock (MES)-induced seizures in mice and rats. In this study, we investigated whether the 2-acetamido moiety was necessary for anticonvulsant activity. Ten derivatives of the known anticonvulsant, N-benzyl 2-acetamido-2-phenyl acetamide were prepared in which the 2-acetamido group was replaced by hydrogen, methyl, oxygen, and halogen substituents. Evaluation of these compounds in the MES-induced seizure test demonstrated that both the hydroxy and the methoxy compounds provided full protection against MES-induced seizures in mice given ip at 100 mg/kg. Moreover, evaluation of the individual stereoisomers for the hydroxy compound showed that the principal activity resided in the (R)-isomer. These findings demonstrated that the 2-acetamido substituent is important but not obligatory for the prevention of MES-induced seizures. Further supporting evidence was provided by comparing the pharmacological activities of N-benzyl 2,3-dimethoxypropionamide with N-benzyl 2-acetamido-3-methoxypropionamide. The ED(50) value for the former in the MES test was 30 mg/kg (ip), which compared favorably with phenobarbital (ED(50) = 22 mg/kg), but the ED(50) value for N-benzyl 2-acetamido-3-methoxypropionamide was 8.3 mg/kg. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0968-0896(96)00225-8
• 作为产物：
  描述：

  N-benzyl-2-hydroxy-2-phenylacetamide 、 甲基磺酰氯 在 吡啶 作用下， 以71%的产率得到[2-(Benzylamino)-2-oxo-1-phenylethyl] methanesulfonate
  参考文献：
  名称：

  N-取代的氨基酸N'-苄基酰胺：合成，抗惊厥和代谢活性。

  摘要：

  制备了氨基酸酰胺（AAA）并在癫痫发​​作模型中进行了评估。AAA在最大的电击惊厥（MES）测试中显示中等至优秀的活性，而在皮下美曲唑诱发的（scMet）惊厥测试中则没有活性。AAA抗惊厥活性既不受C（2）取代基，也不受末端胺取代度的强烈影响。一项体外代谢研究表明，结构-活性关系模式部分归因于在N末端胺单元发生的代谢过程。

  DOI：

  10.1016/j.bmc.2004.02.043

文献信息

• The anticonvulsant activities of functionalized N-benzyl 2-acetamidoacetamides. The importance of the 2-acetamido substituent
  作者：Daeock Choi、James P Stables、Harold Kohn

  DOI：10.1016/s0968-0896(96)00225-8

  日期：1996.12

  Recent studies have demonstrated that substituted N-benzyl 2-acetamidoacetamides provide significant protection against maximal electroshock (MES)-induced seizures in mice and rats. In this study, we investigated whether the 2-acetamido moiety was necessary for anticonvulsant activity. Ten derivatives of the known anticonvulsant, N-benzyl 2-acetamido-2-phenyl acetamide were prepared in which the 2-acetamido group was replaced by hydrogen, methyl, oxygen, and halogen substituents. Evaluation of these compounds in the MES-induced seizure test demonstrated that both the hydroxy and the methoxy compounds provided full protection against MES-induced seizures in mice given ip at 100 mg/kg. Moreover, evaluation of the individual stereoisomers for the hydroxy compound showed that the principal activity resided in the (R)-isomer. These findings demonstrated that the 2-acetamido substituent is important but not obligatory for the prevention of MES-induced seizures. Further supporting evidence was provided by comparing the pharmacological activities of N-benzyl 2,3-dimethoxypropionamide with N-benzyl 2-acetamido-3-methoxypropionamide. The ED(50) value for the former in the MES test was 30 mg/kg (ip), which compared favorably with phenobarbital (ED(50) = 22 mg/kg), but the ED(50) value for N-benzyl 2-acetamido-3-methoxypropionamide was 8.3 mg/kg. Copyright (C) 1996 Elsevier Science Ltd
• N-Substituted amino acid N′-benzylamides: synthesis, anticonvulsant, and metabolic activities
  作者：Cécile Béguin、Arnaud LeTiran、James P. Stables、Robert D. Voyksner、Harold Kohn

  DOI：10.1016/j.bmc.2004.02.043

  日期：2004.6

  Amino acid amides (AAA) were prepared and evaluated in seizure models. The AAA displayed moderate-to-excellent activity in the maximal electroshock seizure (MES) test and were devoid of activity in the subcutaneous Metrazol-induced (scMet) seizure test. The AAA anticonvulsant activity was neither strongly influenced by the C(2) substituent nor by the degree of terminal amine substitution. An in vitro

  制备了氨基酸酰胺（AAA）并在癫痫发​​作模型中进行了评估。AAA在最大的电击惊厥（MES）测试中显示中等至优秀的活性，而在皮下美曲唑诱发的（scMet）惊厥测试中则没有活性。AAA抗惊厥活性既不受C（2）取代基，也不受末端胺取代度的强烈影响。一项体外代谢研究表明，结构-活性关系模式部分归因于在N末端胺单元发生的代谢过程。