Synthesis and in vitro evaluation of novel rhodanine derivatives as potential cholinesterase inhibitors

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F16%3A39901560" target="_blank" >RIV/00216275:25310/16:39901560 - isvavai.cz</a>

Alternative codes found

RIV/00216208:11160/16:10327902

Result on the web

<a href="http://dx.doi.org/10.1016/j.bioorg.2016.07.004" target="_blank" >http://dx.doi.org/10.1016/j.bioorg.2016.07.004</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.bioorg.2016.07.004" target="_blank" >10.1016/j.bioorg.2016.07.004</a>

Result language

angličtina

Original language name

Synthesis and in vitro evaluation of novel rhodanine derivatives as potential cholinesterase inhibitors

Original language description

Based on a broad spectrum of biological activities of rhodanines, we synthesized aromatic amides and esters of 2-(4-oxo-2-thioxothiazolidin-3-yl)acetic acid (rhodanine-3-acetic acid) via carbodiimide- or PCl3-mediated coupling. Both esters and amides were investigated for their in vitro inhibitory potency and selectivity against acetylcholinesterase (AChE) from electric eel and butyrylcholinesterase (BChE) from equine serum using Ellman's spectrophotometric method. The derivatives exhibited mostly a moderate activity against both cholinesterases. IC50 values for AChE were in a closer concentration range of 24.05-86.85 lM when compared to BChE inhibition (7.92-227.19 lM). The esters caused the more efficient inhibition of AChE than amides and parent acid. The esterification and amidation of the rhodanine- 3-acetic acid increased inhibition of BChE, even up to 26 times. Derivatives of 4-nitroaniline/phenol showed the activity superior to other substituents (H, Cl, CH3, OCH3, CF3). Rhodanines produced a balanced inhibition of both cholinesterases. Seven derivatives produced the more potent inhibition of AChE than rivastigmine, a clinically used drug; additional three compounds were comparable. Two amides exceeded inhibitory potency of rivastigmine towards BChE. Importantly, this is the first evidence that rhodanine-based compounds are able to inhibit BChE.

Czech name

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Czech description

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Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

CE - Biochemistry

OECD FORD branch

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Project

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Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2016

Confidentiality

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

Name of the periodical

Bioorganic Chemistry

ISSN

0045-2068

e-ISSN

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Volume of the periodical

68

Issue of the periodical within the volume

October

Country of publishing house

US - UNITED STATES

Number of pages

7

Pages from-to

23-29

UT code for WoS article

000387978400004

EID of the result in the Scopus database

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