Abstract
Herein, we have built up structure–activity relationship (SAR), k-nearest neighbor, quantum mechanical, field similarity analysis as well as a sufficient number of quantitative SAR (QSAR) models to explore the pharmacological activity of Xanthones as α-glucosidase inhibitors. To achieve good results, SAR and QSAR have been investigated apropos of a new descriptor “similarity score”. These analyses reveal that among the various parameters, the softness and the similarity score have high correlation with activity. In addition, structural features like hydrogen bonding ability and steric factors also play a vital role in deciding the α-glucosidase inhibitory activity. The SAR analysis is vindicated by quantum mechanical studies. The best QSAR model was found to have
R
2
= 0.81,
R
adj
2
= 0.79 and
R
CV
2
= 0.76.