Digitální knihovnaUPCE
 

Synthesis of Readily Available Fluorophenylalanine Derivatives and Investigation of Their Biological Activity

ČlánekOmezený přístuppeer-reviewedpublished

Abstrakt

A series of thirty novel N-acetylated fluorophenylalanine-based aromatic amides and esters was synthesized using N-(3-dimethylaminopropyl)-N0-ethylcarbodiimide or phosphorus trichloride in pyridine. They were characterized by spectral methods and screened against various microbes (Mycobacterium tuberculosis, non-tuberculous mycobacteria, other bacteria, fungi), for their inhibition of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) and cytotoxicity. All amino acids derivatives revealed a moderate inhibition of both cholinesterases with IC50 values for AChE and BChE of 57.88–130.75 mM and 8.25–289.0 mM, respectively. Some derivatives were comparable or superior to rivastigmine, an established drug. Phenyl 2-acetamido-3-(4-fluorophenyl)propanoate was identified as the selective and most potent inhibitor of BChE. The esterification and amidation of parent acids led to an improved BChE inhibition. The esters are better inhibitors of BChE than the amides. The introduction of NO2 and CH3 groups into aniline ring and CF3 moiety in phenol is translated into lower IC50 values. Seven compounds showed selectivity index higher than 10 for at least one cholinesterase. Especially the esters exhibited a mild activity against Gram-positive bacteria, mycobacteria and several fungal strains with minimum inhibitory concentrations starting from 125 mM. The highest susceptibility was recorded for Trichophyton mentagrophytes fungus.

Rozsah stran

p. 244-256

ISSN

0045-2068

Trvalý odkaz na tento záznam

Projekt

Zdrojový dokument

Bioorganic Chemistry, volume 71, issue: April

Vydavatelská verze

https://doi.org/10.1016/j.bioorg.2017.02.010

Přístup k e-verzi

Práce není přístupná

Název akce

ISBN

Studijní obor

Studijní program

Signatura tištěné verze

Umístění tištěné verze

Přístup k tištěné verzi

Klíčová slova

Fluorophenylalanine Derivatives, cholinesterases, Biological, Activity, fluorofenylalaninové deriváty, cholinesterázy, biologická aktivita

Endorsement

Review

item.page.supplemented

item.page.referenced