3,5-bis(N,N-dimethylcarbamyloxy)metaproterenol | 801977-26-4

• 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: 3,5-bis(N,N-dimethylcarbamyloxy)metaproterenol
• 英文别名: 3-[(dimethylcarbamoyl)oxy]-5-{1-hydroxy-2-[(propan-2-yl)amino]ethyl}phenyl N,N-dimethylcarbamate；[3-(dimethylcarbamoyloxy)-5-[1-hydroxy-2-(propan-2-ylamino)ethyl]phenyl] N,N-dimethylcarbamate
• CAS: 801977-26-4
• 化学式: C₁₇H₂₇N₃O₅
• 分子量: 353.418
• InChiKey: WBJSMBPZUZZBHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  91.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,5-bis(N,N-dimethylcarbamyloxy)metaproterenol 在 盐酸 作用下， 以 异丙醇 为溶剂， 生成 3-[(dimethylcarbamoyl)oxy]-5-{1-hydroxy-2-[(propan-2-yl)amino]ethyl}phenyl N,N-dimethylcarbamate
  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：

  3,5-二羟基苯乙酮 在 吡啶 、 盐酸 、 sodium tetrahydroborate 、 potassium carbonate sesquihydrate 、 potassium carbonate 、 copper(I) bromide 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 氯仿 、 水 、 乙酸乙酯 、 异丙醇 为溶剂， 反应 10.83h， 生成 3,5-bis(N,N-dimethylcarbamyloxy)metaproterenol
  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