4-Mercaptoimidazoles derived from the naturally occurring antioxidant ovothiols 2. Computational and experimental approach of the radical scavenging mechanism.
Détails
ID Serval
serval:BIB_7ECDB53DBDCB
Type
Article: article d'un périodique ou d'un magazine.
Collection
Publications
Institution
Titre
4-Mercaptoimidazoles derived from the naturally occurring antioxidant ovothiols 2. Computational and experimental approach of the radical scavenging mechanism.
Périodique
Free radical research
ISSN
1071-5762 (Print)
ISSN-L
1029-2470
Statut éditorial
Publié
Date de publication
06/2000
Peer-reviewed
Oui
Volume
32
Numéro
6
Pages
525-533
Langue
anglais
Notes
Publication types: Journal Article
Publication Status: ppublish
Publication Status: ppublish
Résumé
The radical-scavenging mechanism of fourteen 4-mercaptoimidazoles, derived from the natural family of ovothiols, was studied via a QSAR approach, cyclic voltammetry, ESR and NMR spectroscopy. A significant correlation was found between the DPPH scavenging abilities of test compounds and thermodynamic parameters like overall ease of disulphide formation. The production of a disulphide compound via thiyl radical formation is proposed. Upon DPPH scavenging, hydrogen abstraction from thiols yields transient short-lived thiyl radicals, which were characterised by ESR and rapidly dimerise to form a disulphide compound. Cyclic voltammetry showed that the best DPPH scavengers exhibit low oxidation potentials for their oxidation to disulphides.
Mots-clé
Antioxidants/chemistry, Bepridil/analogs & derivatives, Bepridil/chemistry, Biphenyl Compounds, Electrochemistry, Electron Spin Resonance Spectroscopy, Free Radical Scavengers, Free Radicals, Hydroxyl Radical/chemistry, Imidazoles/chemistry, Imidazoles/pharmacology, Methylhistidines/chemistry, Molecular Structure, Picrates, Structure-Activity Relationship, Sulfhydryl Compounds/chemistry, Thermodynamics
Pubmed
Web of science
Création de la notice
22/01/2019 11:29
Dernière modification de la notice
21/08/2019 6:37