87102-64-5

Usage

Uses

Intermediate in the preparation of Propranolol.

Upstream product

• 2461-42-9 3-(1-naphthyloxy)-1,2-epoxypropane 
• 90-15-3 α-naphthol 

Downstream Products

• 4199-09-1 (S)-1-isopropylamino-3-(1-naphthyloxy)-2-propanol 

Relevant academic research and scientific papers

Facile microwave-assisted synthesis and antitubercular evaluation of novel aziridine derivatives

Novel 2-(aryloxymethyl)aziridines and 2-((3-aryl-1-phenylallyloxy)methyl)aziridine derivatives were prepared via ring-opening reaction of epoxides. The synthesized derivatives were characterized by using elemental analysis (EA), FT-IR, 13C NMR, and 1H NMR. The in vitro antitubercular activities of the synthesized compounds were evaluated against Mycobacterium tuberculosis H37Rv (MTB H37Rv) strain using MTT-MABA assay. All the aziridine derivatives exhibited improved persuasive antitubercular activity against MTB H37Rv in comparison with standard drugs. Among the tested compounds, 2-(naphthalene-1-yloxy) methyl aziridine (5b), 2-(naphthalene-2-yloxy)methylaziridine (5c), 2-(m-tolyloxymethyl)aziridine (5e), 2-(3-(4-methoxyphenyl)-1-phenylalloxy)methylaziridine (12b) and 2-(3-(2-chlorophenyl)-1-phenylallyloxy)methylaziridine (12c) revealed promising activity against MTB H37Rv. Specifically, compound 5b and 12 b showed three-times more active (MIC = 0.5 μg/mL) than the standard drugs ethambutol (MIC = 1.56 μg/mL) and ciprofloxacin (MIC = 1.56 μg/mL).

Dynamic kinetic resolution of β-azido alcohols. An efficient route to chiral aziridines and β-amino alcohols

Enzymatic resolution of β-azido alcohols in combination with ruthenium-catalyzed alcohol isomerization led to a successful dynamic kinetic resolution. A variety of racemic β-azido alcohols were efficiently transformed to the corresponding enantiomerically pure acetates (ee up to 99% and conversion up to 98%). The synthetic utility of this procedure has been illustrated by the practical synthesis of (S)-propanolol I and (R)-β-azido-α-(4-methoxyphenyl)ethanol ((R)-1c), a direct precursor of denopamine II.

Resolution of racemic 1-azido-3-aryloxy-2-propanols by lipase-catalyzed enantioselective acetylation

Kinetic resolution of racemic 1-azido-3-aryloxy-2-propanols 1a-g was performed using supported lipase of Candida antarctica-B (Novozym() SP 435) in toluene at 4°C with isopropenyl acetate as the acyl donor to afford the optically active (S)-alcohols 2a-g and their corresponding (R)-acetates 3a-g with E values from 56 to 72. Copyright (C) 2000 Elsevier Science Ltd.

Lipase-catalyzed kinetic resolution of the racemic mixtures of 1- aryloxy-3-nitrato-and-1-aryloxy-3-azido-2-propanols

The racemic mixtures of 1-aryloxy-3-nitrato-2-propanols and 1-aryloxy- 3-azido-2-propanols were resolved with moderate selectivity by the lipase- mediated acylation with vinyl acetate. The effects of the nature, position, and spatial requirements of the p

Synthesis and Chromatographic Separation of the Glucuronides of (R)- and (S)-Propranolol

One of the major metabolites of propranolol (Inderal) is the O-glucuronide.In order to further study its disposition, possible metabolism, and contribution to the antihypertensive effect of propranolol, we have synthesized and separated the two diastereometric propranolol O-β-D-glucuronides (9a,b).These compounds were prepared by reaction of naphthol with epichlorohydrin and treatment of the resulting (2RS)-1'-(2,3-epoxypropoxy)naphthalene (2) with sodium azide to give (2RS)-1-(1'-naphthoxy)-3-azido-2-propanol (3).Alkylation of 3 with methyl (2,3,4-tri-O-acetyl-1-bromo-1-deoxy-α-D-glucopyranosid)uronate (4) gave methyl (2RS)-uronate (5a,b).Reductive alkylation, followed by HPLC separation of the diastereomers, gave methyl (2R)- and (2S)-uronate (6a,b).Hydrolytic removal of the acetyl and methyl protecting groups gave the free glucuronides, which were then converted to the sodium salts, 9a,b.The stereochemistry of the glycoside linkage was deduced from the 400-MHz 1H NMR spectra.The absolute configuration of the aglycon portion was determined after Glusulase hydrolysis by derivatization with (R)-(+)- or-(-)-α-methylbenzyl isocyanate and comparison of the HPLC retention volumes with those of derivatized reference (R)- and (S)-propranolols.