5790-46-5

Usage

Uses

Used in Pharmaceutical Industry:
1-(Isopropylamino)-3-(4-methylphenoxy)propane-2-ol is used as an impurity in the production of Bisoprolol (B510500), a selective β-adrenergic blocker. It plays a role in the development and formulation of antihypertensive medications, contributing to the treatment of high blood pressure.
As an antihypertensive agent, Bisoprolol works by blocking the action of adrenaline on the heart, which reduces the heart rate and the force of heart contractions. This, in turn, lowers the blood pressure and reduces the workload on the heart, making 1-(Isopropylamino)-3-(4-methylphenoxy)propane-2-ol an essential component in the development of such life-saving medications.

Upstream product

• 2186-24-5 cresyl-glicidyl ether 
• 75-31-0 isopropylamine 
• 4769-74-8 1-chloro-3-(4-methylphenoxy)-2-propanol 

Downstream Products

• 80176-44-9 3-Butyl-1-(2-hydroxy-3-p-tolyloxy-propyl)-1-isopropyl-urea 
• 86554-50-9 C₁₇H₂₇N₃O₄ 

Relevant academic research and scientific papers

Process for the solid state synthesis of enantiopure B-aminoalcohols from racemic epoxides

The invention relates to a process for the solid state synthesis of enantiopure β-aminoalcohols by preparing inclusion complexes of aryloxyepoxide with cyclodextrin by adding an epoxide in equimolar ratio in an organic solvent to an aqueous solution of cyclodextrin, reacting the cyclodextrin complex of aryloxyepoxide with a nucleophile in solid state by intimately grinding the mixture using a mortar and pestle, continuing the mixing till the starting epoxide disappeared on tic, removing excess amines under vacuum, extracting the β-aminoalcohols produced with a solvent with yields of more than 50% and enantioselectivity of upto 100%.

Alteration of relative affinities toward myocardial and vascular β adrenoceptors induced by side-chain substitution of aryloxypropanolamines1

Several conformationally defined aryloxypropanolamines of the type ArOCH2CH(OH)CH(R)NHR1 have been synthesized and tested in vivo for β-adrenoceptor blockade. Key intermediates in the syntheses were the appropriate cis- and trans-disubstituted olefins. Epoxidation of the olefins, followed by amination of the resulting cis- and trans-epoxides, yielded the desired diastereomeric model compounds with a defined threo and erythro stereochemistry, respectively. All active compounds in this series exhibit a simple, bimolecular, competitive antagonism at β adrenoceptors. Proper substitutions of the alkanolamine side chain result in vascular selective or cardioselective β-adrenoceptor antagonists, probably as a consequence of the sterically altered ability to interact with β1 and β2 adrenoceptors. dl-erythro-1-Phenoxy-3-[3,4-dimethoxyphenethyl)amino] butan-2-ol is a cardioselective β-adrenoceptor antagonist with a selectivity ratio significantly higher than that of practolol (β1/β2>40 vs. β1/β2=22) but of equal potency (pA2 values = 6.66 and 6.64, respectively). Phenyl substitution at C-3 of the alkanolamine side chain drastically reduces affinity to both types of β adrenoceptors (pA25.0), thus representing a cutoff point. It is concluded that steric factors, as manifested by bulk tolerance at various parts of the aryloxypropanolamine side chain, are major determinants of affinity toward β-adrenoceptor subtypes. β-Adrenoceptor blockade is unrelated to the lipophilic character of the test compounds.