Journal of Computer-Aided Molecular Design

, Volume 27, Issue 11, pp 951–964 | Cite as

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

  • El Hassane Anouar
  • Salwa Raweh
  • Imene Bayach
  • Muhammad Taha
  • Mohd Syukri Baharudin
  • Florent Di Meo
  • Mizaton Hazizul Hasan
  • Aishah Adam
  • Nor Hadiani Ismail
  • Jean-Frédéric F. Weber
  • Patrick Trouillas
Article

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.

Keywords

Schiff bases Antioxidant DFT Kinetics Free radical scavenging BDE Structure–activity relationship 

Supplementary material

10822_2013_9692_MOESM1_ESM.docx (49 kb)
Supplementary material 1 (DOCX 49 kb)

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Copyright information

© Springer Science+Business Media Dordrecht 2013

Authors and Affiliations

  • El Hassane Anouar
    • 1
  • Salwa Raweh
    • 1
    • 2
  • Imene Bayach
    • 1
    • 3
  • Muhammad Taha
    • 1
  • Mohd Syukri Baharudin
    • 1
  • Florent Di Meo
    • 4
  • Mizaton Hazizul Hasan
    • 2
  • Aishah Adam
    • 2
  • Nor Hadiani Ismail
    • 1
    • 5
  • Jean-Frédéric F. Weber
    • 1
    • 2
  • Patrick Trouillas
    • 4
    • 6
    • 7
  1. 1.Atta-ur-Rahman Institute for Natural Product Discovery (RiND)Universiti Teknologi MARAShah AlamMalaysia
  2. 2.Faculty of PharmacyUniversiti Teknologi MARAShah AlamMalaysia
  3. 3.LCSN-Faculté de PharmacieUniversité de LimogesLimogesFrance
  4. 4.INSERM, UMR-S850/Faculté de PharmacieUniversité de LimogesLimogesFrance
  5. 5.Faculty of Applied SciencesUniversiti Teknologi MARAShah AlamMalaysia
  6. 6.Laboratoire de Chimie des Matériaux NouveauxUniversité de MonsMonsBelgium
  7. 7.Regional Center of Advanced Technologies and Materials, Department of Physical Chemistry, Faculty of SciencePalacký UniversityOlomoucCzech Republic

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