2'-chloro-3,4-di(N,N-dimethylcarbamyloxy)acetophenone | 1392302-64-5

• 英文名称: 2'-chloro-3,4-di(N,N-dimethylcarbamyloxy)acetophenone
• CAS: 1392302-64-5
• 化学式: C₁₄H₁₇ClN₂O₅
• 分子量: 328.752
• InChiKey: MGRYWGOXGFSPKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.23
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  76.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2'-chloro-3,4-di(N,N-dimethylcarbamyloxy)acetophenone 在 盐酸 、 (-)-diisopinocamphenylborane chloride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 、 异丙醇 为溶剂， 反应 62.33h， 生成 (R)-3,4-bis(N,N-dimethylcarbamyloxy)isoproterenol
  参考文献：
  名称：

  Metaproterenol, Isoproterenol, and Their Bisdimethylcarbamate Derivatives as Human Cholinesterase Inhibitors

  摘要：

  Metaproterenol and isoproterenol are bronchodilators that provide a structural basis for many other bronchodilators currently in use. One of these structurally related bronchodilators is terbutaline; it is administered as a prodrug, bambuterol, and is metabolized (bioconverted) into terbutaline by butyrylcholinesterase (BChE). The metabolism rate can be affected by BChE gene polymorphism in the human population and BChE stereoselectivity. The aim of our study was to investigate inhibition of human BChE and acetylcholinesterase (AChE) with metaproterenol, isoproterenol, and newly synthesized racemic bisdimethylcarbamate derivatives of metaproterenol (metacarb) and isoproterenol (isocarb) and their (R)-enantiomers to see if their bioconversion is affected by BChE inhibition in the same way as that for bambuterol. Metacarb and isocarb proved to be selective BChE inhibitors, as they progressively inhibited AChE 960 to 80 times more slowly than BChE(UU). All studied cholinesterases displayed poor affinity for metaproterenol and isoproterenol, yet BChE(UU) had an affinity about five times higher than that of AChE.

  DOI：

  10.1021/jm300289k
• 作为产物：
  描述：

  3,4-二羟基-2'-氯苯乙酮 、 二甲氨基甲酰氯 在 吡啶 、 potassium carbonate sesquihydrate 、 potassium carbonate 作用下， 以 乙酸乙酯 为溶剂， 反应 3.5h， 以40%的产率得到2'-chloro-3,4-di(N,N-dimethylcarbamyloxy)acetophenone
  参考文献：
  名称：

  Metaproterenol, Isoproterenol, and Their Bisdimethylcarbamate Derivatives as Human Cholinesterase Inhibitors

  摘要：

  Metaproterenol and isoproterenol are bronchodilators that provide a structural basis for many other bronchodilators currently in use. One of these structurally related bronchodilators is terbutaline; it is administered as a prodrug, bambuterol, and is metabolized (bioconverted) into terbutaline by butyrylcholinesterase (BChE). The metabolism rate can be affected by BChE gene polymorphism in the human population and BChE stereoselectivity. The aim of our study was to investigate inhibition of human BChE and acetylcholinesterase (AChE) with metaproterenol, isoproterenol, and newly synthesized racemic bisdimethylcarbamate derivatives of metaproterenol (metacarb) and isoproterenol (isocarb) and their (R)-enantiomers to see if their bioconversion is affected by BChE inhibition in the same way as that for bambuterol. Metacarb and isocarb proved to be selective BChE inhibitors, as they progressively inhibited AChE 960 to 80 times more slowly than BChE(UU). All studied cholinesterases displayed poor affinity for metaproterenol and isoproterenol, yet BChE(UU) had an affinity about five times higher than that of AChE.

  DOI：

  10.1021/jm300289k