Antioxidant properties of phenolic Schiff bases: structure-activity relationship and mechanism of action

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F13%3A33148402" target="_blank" >RIV/61989592:15310/13:33148402 - isvavai.cz</a>

Výsledek na webu

<a href="http://dx.doi.org/10.1007/s10822-013-9692-0" target="_blank" >http://dx.doi.org/10.1007/s10822-013-9692-0</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1007/s10822-013-9692-0" target="_blank" >10.1007/s10822-013-9692-0</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Antioxidant properties of phenolic Schiff bases: structure-activity relationship and mechanism of action

Popis výsledku v původním jazyce

Phenolic Schiff bases are known for their diverse biological activities and ability to scavenge free radicals. To elucidate (1) the structure-antioxidant activity relationship of a series of thirty synthetic derivatives of 2-methoxybezohydrazide phenolicSchiff bases and (2) to determine the major mechanism involved in free radical scavenging, we used density functional theory calculations (B3P86/6-31+(d,p)) within polarizable continuum model. The results showed the importance of the bond dissociation enthalpies (BDEs) related to the first and second (BDEd) hydrogen atom transfer (intrinsic parameters) for rationalizing the antioxidant activity. In addition to the number of OH groups, the presence of a bromine substituent plays an interesting role in modulating the antioxidant activity. Theoretical thermodynamic and kinetic studies demonstrated that the free radical scavenging by these Schiff bases mainly proceeds through proton-coupled electron transfer rather than sequential proton l

Název v anglickém jazyce

Antioxidant properties of phenolic Schiff bases: structure-activity relationship and mechanism of action

Popis výsledku anglicky

Phenolic Schiff bases are known for their diverse biological activities and ability to scavenge free radicals. To elucidate (1) the structure-antioxidant activity relationship of a series of thirty synthetic derivatives of 2-methoxybezohydrazide phenolicSchiff bases and (2) to determine the major mechanism involved in free radical scavenging, we used density functional theory calculations (B3P86/6-31+(d,p)) within polarizable continuum model. The results showed the importance of the bond dissociation enthalpies (BDEs) related to the first and second (BDEd) hydrogen atom transfer (intrinsic parameters) for rationalizing the antioxidant activity. In addition to the number of OH groups, the presence of a bromine substituent plays an interesting role in modulating the antioxidant activity. Theoretical thermodynamic and kinetic studies demonstrated that the free radical scavenging by these Schiff bases mainly proceeds through proton-coupled electron transfer rather than sequential proton l

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CF - Fyzikální chemie a teoretická chemie

OECD FORD obor

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Projekt

<a href="/cs/project/ED2.1.00%2F03.0058" target="_blank" >ED2.1.00/03.0058: Regionální centrum pokročilých technologií a materiálů</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2013

Kód důvěrnosti údajů

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

Název periodika

Journal of Computer-Aided Molecular Design

ISSN

0920-654X

e-ISSN

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Svazek periodika

27

Číslo periodika v rámci svazku

11

Stát vydavatele periodika

NL - Nizozemsko

Počet stran výsledku

14

Strana od-do

951-964

Kód UT WoS článku

000328207000003

EID výsledku v databázi Scopus

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