Synthesis, antimicrobial and antiradical activity of (3-alkoxymethyl-4-hydroxyphenyl)propan-1-ones, intermediates of biologically active compounds and activity comparison with 3-(alkoxymethyl)-4-(alkylamino-2-hydroxypropoxyphenyl)alkanones type of beta blockers

A homologous series of (3-alkoxymethyl-4-hydroxyphenyl)propan-1-ones was prepared by the reaction of (3-chloromethyl-4-hydroxyphenyl)propan-1-ones with the corresponding alcohols (methanol – decan-1-ol, propan-2-ol, 2-methylpropan-1-ol, 3-methylbutan-1-ol, cyclopentanol, benzylalcohol) in the presen...

Full description

Saved in:
Bibliographic Details
Published in:EUROPEAN PHARMACEUTICAL JOURNAL 2020-05, Vol.67 (2), p.34-44
Main Authors: Čižmáriková, R., Markuliak, M., Habala, L., Valentová, J., Bilková, A.
Format: Article
Language:English
Subjects:
antimicrobial activity
Antimicrobial agents
antioxidant activity
antiradical activity
Beta blockers
substituted phenols
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A homologous series of (3-alkoxymethyl-4-hydroxyphenyl)propan-1-ones was prepared by the reaction of (3-chloromethyl-4-hydroxyphenyl)propan-1-ones with the corresponding alcohols (methanol – decan-1-ol, propan-2-ol, 2-methylpropan-1-ol, 3-methylbutan-1-ol, cyclopentanol, benzylalcohol) in the presence of sodium hydrogen carbonate. The composition of the synthesised compounds was elucidated by IR, UV and 1 H-NMR and 13 C-NMR spectra. Selected compounds were tested against human pathogens: gram-positive bacterium Staphylococcus aureus (CNCTC Mau 29/58), gram-negative bacterium Escherichia coli (CNCTC 377/79) and yeast Candida albicans (CCM 8186). Their antimicrobial activities were expressed as minimum inhibitory concentrations. Antioxidant activity was determined using DPPH and ABTS .+ methods. It could be shown that both biological activities, antimicrobial and antioxidant, were lower in comparison with the (2 RS )-bis [3-(4-acetyl-2-propoxymethyl)phenoxy-2-hydroxypropyl]isopropylammonium fumarate type of beta blockers.
ISSN:2453-6725
2453-6725
DOI:10.2478/afpuc-2020-0012