3D QSAR and docking study of flavone derivatives as potent inhibitors of influenza H1N1 virus neuraminidase.

abstract Although several flavonoids have been reported to exert inhibitory effects on influenza H1N1 neuramin-idase (NA), little is known about the structure–activity relationship and binding mode. Three dimensionalQSAR (quantitative structure–activity relationship) and molecular docking approaches were applied toexplore the structural requisites of flavone derivatives for NA inhibitory activity. A meaningful QSARmodel with R 2 of 0.5968, Q 2 of 0.6457, and Pearson-R value of 0.8679, was constructed. From the QSARmodel, it could be seen how 6-OH, 3 0 -OH, 4 0 -OH, and 8-position substituent affect the NA inhibitory activ-ity. Molecular docking study between the most active compound and NA suggested that hydrogen bonds,hydrophobic and electrostatic interactions were closely related to NA inhibitory activity, 5-OH and 7-OHmay be essential for this activity. The results provide a set of useful guidelines for the rational design ofnovel NA inhibitors. 2011 Elsevier Ltd. All rights reserved.