SYNTHESIS AND ANTIOXIDANT ACTIVITY OF (E)-3-(3-(4-OXO-4H-CHROMEN-3-YL)ACRYLOYL) 2H-CHROMEN-2-ONE DERIVATIVES

Abstract

The aim is based on the results of the in silico prediction, to obtain and characterize a number of (E)-3-(3-(4-oxo-4H-chromen-3-yl)acryloyl)-2H-chromen-2-one derivatives, and also to study their antioxidant activity.Materials and methods. The synthesis of the target compounds was carried out by condensation of substituted 3-formylchromones and 3-acetylcoumarins under the acid catalysis conditions. 1H NMR spectra were recorded on the instruments of Bruker Avance-400 (400 MHz) and Bruker Avance-300 (300 MHz) in the solutions of CDCl3 or DMSO-d6. Mass spectra (ESI) were obtained on a Finnigan LCQ Advantage mass spectrometer (USA). The melting points of the compounds were determined on a PTP (M) instrument. Quantum-chemical calculations were carried out on the basis of a density functional theory using the Gaussian 09 program using the B3LYP/6-311G (d, p) method, as well as using the Way2Drug (PASS Online) online service. The antiradical activity of the compounds was studied by the DPPH test, and the chelating properties were assessed by the o-phenanthroline method.Results. 15 derivatives of (E)-3-(3-(4-oxo-4H-chromen-3-yl)acryloyl)-2H-chromen-2-one have been obtained and characterized. The calculations based on the density functional theory showed that the highest occupied molecular orbital exhibiting electron-donating properties is localized on the propenone fragment, which confirms the likelihood of the manifestation of antiradical properties. According to the prediction of the probable spectrum of the biological activity, the obtained compounds are more likely to exhibit their direct antioxidant activity. According to the results of the in vitro study of the antioxidant activity, it was found out that compounds 1-15 are the most active in relation to the DPPH radical, which confirms the obtained prognostic data.Conclusion. Thus, based on the in silico prediction data, 15 derivatives of (E)-3-(3-(4-oxo-4H-chromen-3-yl)acryloyl)-2H-chromen-2-one have been obtained and characterized, for which the method antioxidant activity has been studied in vitro. It was found out that compounds 1-15 exhibit the antiradical activity to a large extent.