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

Abstract : 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 phenolic Schiff 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 loss electron transfer, the latter mechanism being only feasible at relatively high pH.
Type de document :
Article dans une revue
Liste complète des métadonnées

https://hal-unilim.archives-ouvertes.fr/hal-00937806
Contributeur : Vincent Sol <>
Soumis le : mardi 28 janvier 2014 - 19:22:20
Dernière modification le : mardi 20 mars 2018 - 16:36:21

Lien texte intégral

Identifiants

Collections

Citation

E.H. Anouar, Salwa Raweh, Imene Bayach, M. Taha, Mohd Syukri Baharudin, et al.. Antioxidant properties of phenolic Schiff bases: Structure-activity relationship and mechanism of action. Journal of Computer-Aided Molecular Design, Springer Verlag, 2013, 27 (11), pp.951-964. ⟨10.1007/s10822-013-9692-0⟩. ⟨hal-00937806⟩

Partager

Métriques

Consultations de la notice

129