Investigation of salicylanilide and 4-chlorophenol-based N-monosubstituted carbamates as potential inhibitors of acetyl- and butyrylcholinesterase

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F18%3A39913001" target="_blank" >RIV/00216275:25310/18:39913001 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/00216208:11160/18:10382547

Výsledek na webu

<a href="http://dx.doi.org/10.1016/j.bioorg.2018.07.017" target="_blank" >http://dx.doi.org/10.1016/j.bioorg.2018.07.017</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.bioorg.2018.07.017" target="_blank" >10.1016/j.bioorg.2018.07.017</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Investigation of salicylanilide and 4-chlorophenol-based N-monosubstituted carbamates as potential inhibitors of acetyl- and butyrylcholinesterase

Popis výsledku v původním jazyce

Based on the presence of carbamate moiety, twenty salicylanilide N-monosubstituted carbamates concomitantly with their parent salicylanilides and five newly prepared 4-chlorophenyl carbamates obtained from isocyanates were investigated using Ellman&apos;s method for their in vitro inhibitory activity against acetylcholinesterase (AChE) from electric eel and butyrylcholinesterase (BChE) from equine serum. The carbamates and salicylanilides exhibited mostly a moderate inhibition of both cholinesterase enzymes with IC(50) values ranging from 5 to 235 mu M. IC(50) values for AChE were in a narrower concentration range when compared to BChE, but many of the compounds produced a balanced inhibition of both cholinesterases. The derivatives were comparable or superior to rivastigmine for AChE inhibition, but only a few of carbamates also for BChE. Several structure-activity relationships were identified, e.g., N-phenethylcarbamates produce clearly favourable BChE inhibition. The compounds also share convenient physicochemical properties for CNS penetration.

Název v anglickém jazyce

Investigation of salicylanilide and 4-chlorophenol-based N-monosubstituted carbamates as potential inhibitors of acetyl- and butyrylcholinesterase

Popis výsledku anglicky

Based on the presence of carbamate moiety, twenty salicylanilide N-monosubstituted carbamates concomitantly with their parent salicylanilides and five newly prepared 4-chlorophenyl carbamates obtained from isocyanates were investigated using Ellman&apos;s method for their in vitro inhibitory activity against acetylcholinesterase (AChE) from electric eel and butyrylcholinesterase (BChE) from equine serum. The carbamates and salicylanilides exhibited mostly a moderate inhibition of both cholinesterase enzymes with IC(50) values ranging from 5 to 235 mu M. IC(50) values for AChE were in a narrower concentration range when compared to BChE, but many of the compounds produced a balanced inhibition of both cholinesterases. The derivatives were comparable or superior to rivastigmine for AChE inhibition, but only a few of carbamates also for BChE. Several structure-activity relationships were identified, e.g., N-phenethylcarbamates produce clearly favourable BChE inhibition. The compounds also share convenient physicochemical properties for CNS penetration.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

30104 - Pharmacology and pharmacy

Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2018

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Bioorganic Chemistry

ISSN

0045-2068

e-ISSN

—

Svazek periodika

80

Číslo periodika v rámci svazku

October

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

6

Strana od-do

668-673

Kód UT WoS článku

000441537800070

EID výsledku v databázi Scopus

2-s2.0-85050533780