3,5-bis-(N,N-dimethylcarbamoyloxy)phenyloxirane | 1392302-60-1

• 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-dimethylcarbamoyloxy)phenyloxirane
• 英文别名: 2-[3,5-di(N,N-dimethylcarbamyloxy)phenyl]oxirane；[3-(dimethylcarbamoyloxy)-5-(oxiran-2-yl)phenyl] N,N-dimethylcarbamate
• CAS: 1392302-60-1
• 化学式: C₁₄H₁₈N₂O₅
• 分子量: 294.307
• InChiKey: KHCRMINTBUGOAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  71.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,5-bis-(N,N-dimethylcarbamoyloxy)phenyloxirane 在 盐酸 作用下， 以 水 、 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：

  班布特罗杂质 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 0.33h， 以85%的产率得到3,5-bis-(N,N-dimethylcarbamoyloxy)phenyloxirane
  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

文献信息

• 一种盐酸班布特罗的合成工艺
  申请人：宏冠生物药业有限公司

  公开号：CN109942462B

  公开（公告）日：2022-01-14

  本发明公开了一种盐酸班布特罗工艺路线，具体说是1‑[双‑(3,5‑N,N‑二甲基氨基甲酰氧基)苯基]‑2‑N‑叔丁氨基乙醇盐酸盐的合成方法。该合成方法操作简单、路线简短、条件温和、环境友好和成品质量高。
• R-bambuterol, its preparation and therapeutic uses
  申请人：Tan Wen

  公开号：US20050171197A1

  公开（公告）日：2005-08-04

  R-enantiomer of Bambuterol, its preparation and therapeutic uses are disclosed. A composition includes R-Bambuterol or its therapeutically acceptable salt. A composition of R-Bambuterol includes at least 80% by weight of the R-enantiomer and not more than 20% by weight of the S-enantiomer based on a total weight of the Bmbuterol. A process includes: (a) asymmetrically reducing a suitably substituted and suitably protected bromoacetophenone compound to a chiral phenyl-bromoethanol comprising a primary bromo group and a secondary hydroxyl group; (b) displacing the bromo group by a suitably substituted and optionally protected primary amine to produce a protected chiral phenylethanolamine, and (c) removing the protecting groups to convert the protected chiral phenylethanolamine to a chiral phenylethanolamine.
• US7495028B2
  申请人：——

  公开号：US7495028B2

  公开（公告）日：2009-02-24