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http://dx.doi.org/10.3839/jabc.2010.018

The Influence of the Substituents on the Benzo Ring for Antioxidant Activity of 4-Methyl-2H-benzopyran-2-one Analogues  

Choi, Won-Seok (Department of Applied Biology & Chemistry, College of Agriculture & Life Sciences, Chungnam National University)
Lee, Jae-Whang (Department of Applied Biology & Chemistry, College of Agriculture & Life Sciences, Chungnam National University)
Cho, Yun-Gi (Department of Applied Biology & Chemistry, College of Agriculture & Life Sciences, Chungnam National University)
Sung, Nack-Do (Department of Applied Biology & Chemistry, College of Agriculture & Life Sciences, Chungnam National University)
Publication Information
Journal of Applied Biological Chemistry / v.53, no.2, 2010 , pp. 99-104 More about this Journal
Abstract
The influences on antioxidant activities of the substituents ($R_1-R_4$) on benzo ring in 4-Methyl-2H-benzopyran-2-one analogues (1-23) were discussed quantitatively using three dimensional quantitative structure-activity relationships (3D-QSARs: Comparative molecular field analyses (CoMFA) and Comparative molecular similarity indice analyses (CoMSIA)) methods. The statistical qualities of CoMSIA models were better than those of CoMFA models and the CoMSIA 2 model was optimized model ($q^2$=0.700 & $r^2$=0.979). Also, the contribution ratios (%) of the optimized CoMSIA 2 model were H-bond donor field 43.5%, electrostatic field 41.8% and steric field 14.7% so that the antioxidant activity exhibited a strong correlation with H-bond donor and electrostatic factor of molecules. From the analytical results of the CoMSIA contour maps, if the positive charge favor group and H-bond donor disfavor group were placed in the $R_1-R_4$ positions on the benzo ring, it was predicted that the groups would raised the antioxidant activity.
Keywords
Antioxidant activity; 3D-QSARs (CoMFA & CoMSIA); 4-Methyl-2H-benzopyran-2-one analogues;
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