The synthesis, molecular structure and spectra properties of sulfur and selenium deferiprone analogues

Abstract

Deferiprone has a broad spectrum of biological effects. Thus it is interesting to investigate the influence of structural changes in deferiprone on its biological activity. This work presents a synthesis of a new selenium analogue of deferiprone, 3-hydroxy-1,2-dimethyl-4(1H)- pyridineselenone (3-HDPSe), and an improved method for synthesis of a sulfur analogue of deferiprone, 3-hydroxy-1,2-dimethyl-4(1H)-pyridinethione (3-HDPT). The structures of the synthesized compounds were confirmed by means of IR, MS, 1H NMR and 13C NMR measurements. Single crystals of the selenium analogue were obtained and the crystal structure determined using X-ray diffraction. Additionally DFT (the B3LYP functional combined with the 6-311++G∗∗ basis set) theoretical calculations were conducted and the results compared with experimental data.