Hybridization of Aminoadamantanes with Cinnamic Acid Analogues and Elucidation of Their Antioxidant Profile
The result's identifiers
Result code in 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>
Result on the web
<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>
Alternative languages
Result language
angličtina
Original language name
Hybridization of Aminoadamantanes with Cinnamic Acid Analogues and Elucidation of Their Antioxidant Profile
Original language description
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'-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) > 4a(6) > CaffA > 4c(5) and 4a(5) > 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.
Czech name
—
Czech description
—
Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
—
OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
—
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2022
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Journal of Chemistry
ISSN
2090-9063
e-ISSN
2090-9071
Volume of the periodical
2022
Issue of the periodical within the volume
November
Country of publishing house
GB - UNITED KINGDOM
Number of pages
11
Pages from-to
7582587
UT code for WoS article
000891078700001
EID of the result in the Scopus database
2-s2.0-85143167668