81732-48-1

Usage

InChI:InChI=1/C14H18N2O5/c1-9(17)10-6-11(20-13(18)15(2)3)8-12(7-10)21-14(19)16(4)5/h6-8H,1-5H3

Upstream product

• 51863-60-6 3,5-dihydroxyacetophenone 
• 79-44-7 N,N-Dimethylcarbamoyl chloride 
• 35086-59-0 1-(3',5'-diacetoxyphenyl)ethanone 

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.

Green synthesis of (R)-terbutaline for recyclable catalytic asymmetric transfer hydrogenation in ionic liquids

We synthesize optically active (R)-terbutaline 2, which is an anti-asthmatic drug, through recyclable catalytic asymmetric transfer hydrogenation (RCATH). Various chloroketones 4 were prepared and RCATH was performed on them. The products exhibit moderate

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.

Design, synthesis, biological evaluation, and molecular modeling studies of chalcone-rivastigmine hybrids as cholinesterase inhibitors

A series of novel chalcone-rivastigmine hybrids were designed, synthesized, and tested in vitro for their ability to inhibit human acetylcholinesterase and butyrylcholinesterase. Most of the target compounds showed hBChE selective activity in the micro- a

Preparation method of bambuterol impurity B

The invention discloses a preparation method of a bambuterol impurity B. The method comprises the following steps: 1. by using 3,5-dihydroxyacetophenone as an initial raw material, completely reacting in the presence of DMF (N,N-dimethylformamide), K2CO3 and N,N-dimethyl formyl chloride at 80 DEG C, filtering, concentrating, and carrying out column chromatography to obtain yellow oil, thereby preparing a compound I; 2. by using the compound I as a substrate, carrying out reflux reaction in the presence of SeO2, dioxane and water, thereby preparing a compound II; and 3. treating the compound II, EtOH and NaBH4 in an ice bath, and reacting at room temperature, thereby preparing a compound III. According to the scheme, the common solvent is adopted for treatment in combination with greenness and environment friendliness; and the ethyl acetate safe solvent is utilized to prepare the bambuterol impurity B. Thus, the technique is easy to operate, has the advantages of low energy consumption and high product purity, and has favorable market application value.

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)

A kind of carbamate-koncar ketone choline esterase inhibitor and its preparation method and application (by machine translation)

The present invention discloses a kind of carbamate-koncar ketone choline esterase inhibitor and its preparation method and application, belongs to the field of medicinal chemistry. Cholinesterase inhibitors of the invention represented by general formula

Bambuterol intermediate preparation process

The invention relates to a preparation process of bambuterol. A homogeneous phase reaction system is formed by using a catalyst 4-dimethylamino-pyridine and an organic alkali reagent, so that a target intermediate is simply and efficiently obtained. The preparation method is high in yield, low in cost and suitable for industrial production.

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.