Synthesis and antioxidant evaluation of 3-bromo-flavone

Abstract

Objective: The objective of the study was to obtain a flavone derivative compound through N-bromosuccinimide (NBS) reducing the reaction. The antioxidant activity of the synthetic compound was then assayed by the 2,2-diphenyl-1-picrylhydrazyl method. Methods: Chalcone (3 mmol) as intermediate precursor was suspended with dimethyl sulfoxide and reacted with NBS (3 mmol), stirred at room temperature for 25 min and diluted in cold water. The synthesis of flavone derivatives resulted in yellow crystalline powder, freely soluble in methanol and ethanol, renamed 60% with a melting point of 87.7°C. Detection by thin-layer chromatography using hexane:chloroform (2:1) showed single spot with Rf = 0.38 which is different from the Rf value of the starting compound (chalcone, 0.66 and 0.78). Results: The results of the characterization of the synthesized compound using ultraviolet-visible and Fourier transform-infared showed the group characteristic containing C=C (1604.77 and 1639.49 cm-1), C=O (1681.93 cm-1), C-O-C (1242.16 cm-1), Ar-H (3032.1 and 3062.96 cm-1), and C-Br (663.51 cm-1) at maximum absorption of wavelength 253 nm. Conclusion: The synthesis of flavone using NBS resulted in 3-bromo-flavone with a weak antioxidant activity.