A theoretical study of radical scavenging antioxidant activity of 3-styrylchromone derivatives using DFT based on quantum chemical descriptors

Chromone (4H-chromen-4-one, 4H-1-benzopyran-4-one) heterocyclic compound has been widely used in traditional medicine, which has anti-allergy, anti-inflammation, anti-diabetes, anti-tumor, antibacterial and other pharmacological effects. To estimate the scavenging activity on free radical of 3-styry...

Full description

Saved in:
Bibliographic Details
Published in:Theoretical chemistry accounts 2021-05, Vol.140 (5), Article 48
Main Authors: Huang, Pei, Jin, Ling-Xia, Lu, Jiu-Fu, Gao, Yan-Hong, Guo, Shao-Bo
Format: Article
Language:English
Subjects:
Antioxidants
Atomic/Molecular Structure and Spectra
Catechol
Chemical properties
Chemistry
Chemistry and Materials Science
Conjugation
Density functional theory
Free radicals
Heterocyclic compounds
Hydrogen bonds
Hydroxyl groups
Inorganic Chemistry
Mathematical analysis
Molecular structure
Organic Chemistry
Physical Chemistry
Quantum chemistry
Regular Article
Scavenging
Theoretical and Computational Chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Chromone (4H-chromen-4-one, 4H-1-benzopyran-4-one) heterocyclic compound has been widely used in traditional medicine, which has anti-allergy, anti-inflammation, anti-diabetes, anti-tumor, antibacterial and other pharmacological effects. To estimate the scavenging activity on free radical of 3-styrylchromone derivatives, we considered the physical and chemical properties of the molecule structure, orbital, and thermodynamics. The antioxidant activity of 3-styrylchromone derivatives was studied by density functional theory (DFT) in gas and water. A series of quantum chemical parameters were calculated to describe molecular properties and clarify the radical scavenging mechanism. Our study suggests that the antioxidant activity of scavenging free radicals is largely affected by molecular structure, especially the number of hydroxyl groups, hydrogen bonds, and conjugation effects. 3-styrylchromone derivatives containing pyrogallol structure may have potential antioxidant activity. The antioxidant ability of catechol structure is greater than pyrogallol structure. 1,4-pyrrole also has a positive effect on free radical scavenging, but the scavenging effect of 2-OH and 5-OH introduced by antioxidants was not obvious. The excellent correlations between the structure and the mentioned DFT-based descriptors lead us to predict good antioxidants.
ISSN:1432-881X
1432-2234
DOI:10.1007/s00214-021-02754-9