Assessing the pharmacological potential of selected xanthene derivatives Scientific paper

Abstract

A convenient and efficient approach toward the synthesis of seven aromatically substituted xanthendiones 1‒7 and one structurally-related xan­thenone 8 through condensation of dimedone and the appropriate aromatic ald­e­hyde is reported. Further, their chemical structure was confirmed by melting points, elemental analysis, FT-IR, ¹H-, ¹³C-NMR and UV–Vis spectroscopic methods. The relationship between the chemical structure and pharmacological activity was determined empirically using appropriate software packages and in vitro using the 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid (ABTS) method. The results of in silico prediction suggested that all investigated com­pounds possess good oral bioavailability. The results of the ABTS assay indic­ate that five compounds possess the ability to scavenge the ABTS^•+ radical cat­ion. Based on the comparison of the IC₅₀ values, the activity of the compounds was found to be as follows: 6 > 1 > 7 > 2 > 8. The effects of solvent dipol­arity/polarizability and solute solvent–hydrogen-bonding interactions on the shifts of the absorption maxima were rationalized by means of the linear sol­vation energy relationship concepts proposed by Kamlet–Taft and Catalán.