81732-49-2

Usage

Uses

Used in Pharmaceutical Industry:
5-(Bromoacetyl)-1,3-phenylene bis(dimethylcarbamate) is used as an intermediate in the synthesis of 1-Keto Bambuterol Hydrochloride (K171500), which is an impurity of Bambuterol (B117500). This application is crucial for the development and production of Bambuterol, a medication used to treat asthma and chronic obstructive pulmonary disease (COPD). Its role in the synthesis process ensures the quality and purity of the final pharmaceutical product.

InChI:InChI=1/C14H17BrN2O5/c1-16(2)13(19)21-10-5-9(12(18)8-15)6-11(7-10)22-14(20)17(3)4/h5-7H,8H2,1-4H3

Upstream product

• 35086-59-0 1-(3',5'-diacetoxyphenyl)ethanone 
• 51863-60-6 3,5-dihydroxyacetophenone 
• 81732-48-1 bis-3,5-(N,N-dimethylcarbamoyloxy)-acetophenone 

Downstream Products

• 1027450-75-4 (R)-1-bromo-2-[3,5-bis(N,N-dimethylcarbamyloxy)phenyl]-2-ethanol 
• 1392396-73-4 (R)-3,5-bis(N,N-dimethylcarbamyloxy)metaproterenol 
• 1050279-04-3 (R)-2-[3,5-di(N,N-dimethylcarbamyloxy)phenyl]oxirane 
• 1392302-62-3 3-[(dimethylcarbamoyl)oxy]-5-{1-hydroxy-2-[(propan-2-yl)amino]ethyl}phenyl N,N-dimethylcarbamate 
• 1392302-60-1 2-[3,5-di(N,N-dimethylcarbamyloxy)phenyl]oxirane 
• 801977-26-4 3,5-bis(N,N-dimethylcarbamyloxy)metaproterenol 
• 788821-30-7 (R)-2-(tert-butylamino)-1-[3,5-bis(dimethylcarbamoyloxy)phenyl]ethanol 

Relevant academic research and scientific papers

Synthetic process of Bambuterol hydrochloride

The invention discloses a synthetic process of Bambuterol hydrochloride and particularly discloses a synthetic method of 1-[bis-(3,5-N,N-dimethylcarbamoyloxy)phenyl]-2-N-tert-butylaminoethanol hydrochloride. The synthetic method is easy in operation, short in route, mild in condition, environment-friendly and high in finished product quality.

Design, synthesis and biological evaluation of bambuterol analogues as novel inhibitors of butyrylcholinesterase

An increase activity of butyrylcholinesterase is believed to contribute to Alzheimer's disease. Bambuterol is a known potent inhibitor of butyrylcholinesterase, but it has undesired cardiac effects and less lipophilicity. Thirteen bambuterol analogues were synthesized using 1-(3, 5-dihydroxyphenyl) ethanone as a starting material. In-vitro cholinesterase assay established that the majority of the compounds are specific butyrylcholinesterase inhibitors. Out of the 13 compounds, two bambuterol derivatives, BD-6 and BD-11 exhibited similar efficacies in inhibiting butyrylcholinesterase with fewer effects on heart and enhanced possibilities of permeating through the blood-brain barrier as compared to bambuterol. These bambuterol analogues may provide better alternatives for treatments of Alzheimer's disease.

A compound and its preparation method and application (by machine translation)

This invention discloses a kind of compound, preparation method and application thereof, belongs to the field of medicine. The compound is 1 - [di-(3 the [...], 5 the [...] -N, N-dimethylamino formyloxy) phenyl] - 2-N-tert-butyl amino ethanol derivatives, the chemical structure formula such as formula (I) is shown. This compound has prominent inhibition of butyryl choline esterase, can be used as a the use of butyryl choline esterase inhibitors. Also may be used in preparing the butyrylcholinesterase for the treatment of diseases associated to be applied to the drug. (by machine translation)

Synthesis of stable isotope labeled D9-Mabuterol, D9-Bambuterol, and D9-Cimbuterol

Three stable and simple synthetic routes of labeled D9-Mabuterol, D9-Bambuterol, and D9-Cimbuterol were described with 98.5%, 99.7%, and 98.4% isotopic abundance and good purity. These structures and isotope-abundance were confirmed according to 1H NMR and liquid chromatography-tandem mass spectrometry.

Synthesis of (R)-bambuterol based on asymmetric reduction of 1-[3,5-bis(dimethylcarbamoyloxy)phenyl]-2-chloroethanone with incubated whole cells of Williopsis californica JCM 3600

To achieve the synthesis of (R)-bambuterol, a prodrug of (R)-terbutaline, asymmetric reduction of 1-[3,5-bis(dimethylcarbamoyloxy)phenyl]-2-chloroethanone with whole cells of Williopsis californica JCM 3600 pre-incubated on glycerol as a carbon source was examined. Initially, the insolubility of this crystalline substrate (mp 126-127 C) in the incubation broth was an obstacle that needed to be overcome. To solve the problem, the concentration of glycerol was increased to 10% during reduction. Glycerol worked well for recycling oxido-reduction cofactors and for enhancing the water solubility of the substrate. The reduction proceeded smoothly to give enantiomerically pure (R)-alcohol in 81% isolated yield.

Metaproterenol, isoproterenol, and their bisdimethylcarbamate derivatives as human cholinesterase inhibitors

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 BChEUU. All studied cholinesterases displayed poor affinity for metaproterenol and isoproterenol, yet BChE UU had an affinity about five times higher than that of AChE.