Hybridization of Aminoadamantanes with Cinnamic Acid Analogues and Elucidation of Their Antioxidant Profile

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F22%3A10451906" target="_blank" >RIV/00216208:11310/22:10451906 - isvavai.cz</a>

Výsledek na webu

<a href="https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=dLBZRN5SFU" target="_blank" >https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=dLBZRN5SFU</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1155/2022/7582587" target="_blank" >10.1155/2022/7582587</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Hybridization of Aminoadamantanes with Cinnamic Acid Analogues and Elucidation of Their Antioxidant Profile

Popis výsledku v původním jazyce

A series of seventeen cinnamic acid hybrids (4a(i)-c(i)) were obtained through an amidation of aminoadamantanes (amantadine, rimantadine, and memantine) with mixed anhydride generated from different substituted cinnamic acid and ethyl chloroformate. (1)H NMR, (13)C NMR, IR, and HRMS were used for the confirmation of the structures of the synthesized hybrids. Moreover, the antioxidant profiles of amides were estimated as per five different in vitro methods: 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2,2&apos;-azinobis-3-ethylbenzothiazoline-6-sulfonic acid cation radical (ABTS+), ferric reducing antioxidant power (FRAP), cupric reducing antioxidant capacity (CUPRAC) assay, and inhibition of Fe(III)/asc induced lipid peroxidation (LP) in brain homogenate. For comparison, caffeic acid (CaffA), known as a potent naturally occurring antioxidant, was used as a reference compound in our study. The results revealed that the most prominent antioxidant activity was demonstrated by compound 4b(2), with excellent CUPRAC, FRAP, scavenging ABTS(+) potential, and inhibition of Fe/asc-induced LP, followed by 4c(6) &gt; 4a(6) &gt; CaffA &gt; 4c(5) and 4a(5) &gt; 4a(7). Overall, the results suggest that the hybrids (4b(2), 4c(6), and 4a(6)) consisting of a caffeoyl moiety and lipophilic adamantane core endow the molecules with the higher antioxidant activity than their parent compound (caffeic acid), especially against LP. Thus, these promising antioxidants could have beneficial effects in various pathological conditions, where oxidative stress is implicated.

Název v anglickém jazyce

Hybridization of Aminoadamantanes with Cinnamic Acid Analogues and Elucidation of Their Antioxidant Profile

Popis výsledku anglicky

A series of seventeen cinnamic acid hybrids (4a(i)-c(i)) were obtained through an amidation of aminoadamantanes (amantadine, rimantadine, and memantine) with mixed anhydride generated from different substituted cinnamic acid and ethyl chloroformate. (1)H NMR, (13)C NMR, IR, and HRMS were used for the confirmation of the structures of the synthesized hybrids. Moreover, the antioxidant profiles of amides were estimated as per five different in vitro methods: 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2,2&apos;-azinobis-3-ethylbenzothiazoline-6-sulfonic acid cation radical (ABTS+), ferric reducing antioxidant power (FRAP), cupric reducing antioxidant capacity (CUPRAC) assay, and inhibition of Fe(III)/asc induced lipid peroxidation (LP) in brain homogenate. For comparison, caffeic acid (CaffA), known as a potent naturally occurring antioxidant, was used as a reference compound in our study. The results revealed that the most prominent antioxidant activity was demonstrated by compound 4b(2), with excellent CUPRAC, FRAP, scavenging ABTS(+) potential, and inhibition of Fe/asc-induced LP, followed by 4c(6) &gt; 4a(6) &gt; CaffA &gt; 4c(5) and 4a(5) &gt; 4a(7). Overall, the results suggest that the hybrids (4b(2), 4c(6), and 4a(6)) consisting of a caffeoyl moiety and lipophilic adamantane core endow the molecules with the higher antioxidant activity than their parent compound (caffeic acid), especially against LP. Thus, these promising antioxidants could have beneficial effects in various pathological conditions, where oxidative stress is implicated.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2022

Kód důvěrnosti údajů

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

Název periodika

Journal of Chemistry

ISSN

2090-9063

e-ISSN

2090-9071

Svazek periodika

2022

Číslo periodika v rámci svazku

November

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

11

Strana od-do

7582587

Kód UT WoS článku

000891078700001

EID výsledku v databázi Scopus

2-s2.0-85143167668