This research communication is toward the investigation of the antibacterial, antifungal and antioxidant activities of the synthesized compounds 1-(4'-O-β-D-glucopyranosyloxy-2'-hydroxyphenyl)-3-aryl-propane-1,3-diones (5a)-(5h). These compounds have been obtained by the interaction of α-acetobromoglucose with 1-(2',4'-dihydroxyphenyl)-3-aryl-propane-1,3-diones (3a)-(3h) under anhydrous condition and at lower temperature. The structures of these newly synthesized O-β-D-glucopyranosides were established on the basis of chemical, elemental, and spectral analyses. Further, the compounds (5b), (5c), (5d) and (5g) showed potent antibacterial and antifungal activity. A good correlation was obtained between the theoretical predictions of bioavailability using Lipinski's rule-of-five and experimental verification.