title: Ligand-based CoMFA and CoMSIA studies on chromone derivatives as radical scavengers.
abstract: The antioxidant activity for a series of chromone compounds, evaluated by DPPH free radical scavenging assay, were subjected to 3D-QSAR studies using comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA). All 48 chromone derivatives were geometry optimized by AM1 and HF/6-31G(*) calculations. The CoMFA and CoMSIA results were compared between different alignment strategies. The best CoMFA model obtained from HF/6-31G(*) optimization with field fit alignment gave cross-validated r(2) (q(2))=0.821, noncross-validated r(2)=0.987, S=0.095, and F=388.255. The best CoMSIA model derived from AM1 optimized structures and superimposition alignment gave q(2)=0.876, noncross-validated r(2)=0.976, S=0.129, and F=208.073, including electrostatic, hydrophobic, hydrogen bond donor and acceptor fields. The contour maps provide the fruitful structure-radical scavenging activity relationships which are useful for designing new compounds with higher activity.
authors.affiliation: Faculty of Pharmacy, Siam University, 38 Petkasem Road, Bangkok 10160, Thailand.
authors.forename: Narumol
authors.initials: N
authors.lastname: Phosrithong
authors.forename: Jiraporn
authors.initials: J
authors.lastname: Ungwitayatorn
mesh_terms: D002867:Chromones / Q000737:chemistry*; D016166:Free Radical Scavengers / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D021281:Quantitative Structure-Activity Relationship
chemical_list: D002867:Chromones; D016166:Free Radical Scavengers; D008024:Ligands
keywords: Chromone derivatives; CoMFA; CoMSIA; Radical scavenging activity