| Abstract
| - Flavonoids, generated by plants upon attack by a range of pathogens, are demonstrated to have arole in biotic and abiotic stress response phenomena in plants, and there is increasing evidence forthe antibacterial, antifungal, and antiviral activities of these compounds. Using the bioisosterismstrategy, a series of 2-aryl-4-chromanone derivatives based upon the structure of flavanones, a kindof flavonoid phytoalexins, were synthesized and tested for the antifungal activity against Pyriculariagrisea, which have been reported in our previous papers. To further explore the comprehensivestructure−activity relationship and construct the binding model for the antifungal compounds, twokinds of molecular field analysis techniques, comparative molecular field analysis (CoMFA) andcomparative molecular similarity indices analysis (CoMSIA), were performed following a Hansch−Fujita QSAR study. Superimpositions were performed using three alignment rules, that is, centroid-based alignment, common substructure-based alignment, and field fit alignment, and statisticallyreliable models with good predictive power (CoMFA r2 = 0.952, q2 = 0.727; CoMSIA r2 = 0.965, q2= 0.751) were achieved on the basis of the common substructure-based alignment. The combinedresults of CoMFA, CoMSIA, and former Hansch−Fujita QSAR analyses resulted in comprehensiveunderstanding about the structure−activity relationships, which led to this construction of a plausiblebinding model of the title compounds. Keywords: CoMFA; CoMSIA; Hansch−Fujita QSAR; 2-aryl-4-chromanones derivatives; binding model
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