Synthesis, biopharmaceutical characterization, antimicrobial and antioxidant activities of 1-(4′-O-β-d-glucopyranosyloxy-2′-hydroxyphenyl)-3-aryl-propane-1,3-diones

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.

Graphical abstractA novel series of 1-(4′-O-β-d-glucopyranosyloxy-2′-hydroxyphenyl)-3-aryl-propane-1,3-diones have been evaluated for their biopharmaceutical, antimicrobial and antioxidant, properties.Figure optionsDownload full-size imageDownload as PowerPoint slideResearch highlights► This research article highlights the finding of novel antimicrobial and antioxidant agent 1-(4′-O-β-d-glucopyranosyloxy-2′-hydroxyphenyl)-3-aryl-propane-1,3-diones. ► The presence of glucosyl moiety in the compounds increased its significant hydrophilic nature. With the help of computational hypothesis it is predicted that most of these compounds could be used without great risk of toxicity in diverse antibacterial activity. ► Some compounds (5b), (5c), (5d) and (5g) were found to be potent antibacterial and antifungal agents comparable with standard drugs Ampicillin and Fluconazole.