Synthesis, Characterization and Biological Evaluation of Aurone and Chromone Derivatives

Abstract

In the present research, various aurone and chromone derivatives (1-90) were designed and synthesized through two and three-step reactions respectively and evaluated for their in vitro mushroom tyrosinase, -amylase, -glucosidase and alkaline phosphatase inhibition activities. Chalcones were synthesized through Claisen-Schmidt condensation then oxidatively cyclized in the presence of a catalytic amount of H2O2 (flavonols), I2/DMSO (flavones) and Hg(OAc)2 to produce a substituted aurones. The molecular structures of all the synthesized compounds were substantiated by different spectroscopic techniques (UV-Vis, FT-IR, mass spectrometry, 1H-NMR and 13C-NMR). Moreover, the synthesized aurone and chromone (flavones and flavonols) derivatives (1-90) were examined for their antioxidant and antimicrobial activities. Biological evaluation exhibited moderate to excellent activities against different bacterial and mycological strains and their action is analogous to those of commercially existing antibiotics i.e., clotrimazole and cefixime. Activities displayed by both scaffolds might be due to the collective impact of the heteroatom as well as different substituents present on rings A and B. The results demonstrated that most of the synthesized compounds were better inhibitors of mushroom tyrosinase with varying degrees of IC50 values. Inhibitory activities of these target compounds are highly reliant on the position and nature of different substituents on Rings A & B of the designed motifs/scaffolds. This study helps to design and develop novel inhibitors by using 2-arylchromone and 2-benzylidenefuran as a structural core in the time ahead. We are very confident that these results might be of interest in medicinal chemistry applications.