A new series of eight compounds 1-(40 -O-b-Dglucopyranosyloxy-20 -hydroxy-50 -substituted phenyl)-3 heteroaryl-propane-1,3-diones (DKG) were prepared by the interaction of a-acetobromoglucose with 1-(20 ,40 -dihydroxy-50 -substituted phenyl)-3-heteroaryl-propane-1,3-diones under anhydrous condition at lower temperature. The structures of these O-b-D-glucopyranosides were established on the basis of chemical, elemental, and spectral analyses. Further, the compounds were tested for their antibacterial, antifungal, and antioxidant properties. A correlation of structure and activities relationship of these compounds with respect to molecular modeling, Lipinski rule of five, drug-likeness, toxicity profiles, and other physicochemical properties of drugs are described and verified experimentally.