Synthesis and characterization of thiazolidine-4-one compounds derived from chalcone and evaluation of the biological activity of some of them

Abstract

In this paper, chalcone [T1-T10] was synthesized from the reaction of (N-phenylacetamide or N-(4-chlorophenyl)acetamide) with benzaldehyde and its aromatic substitutes using ethanol as a solvent and in the presence of KOH as a basic intermediate. Schiff bases [T11-T20] were synthesized from the reaction of chalcone [T1-T10] with 4-chloroaniline using droplets of glacial acetic acid and in the presence of ethanol as a solvent. Thiazolidines-4-one compounds were synthesized from the reaction of Schiff bases [T11-T20] prepared in the second step with thioglycolic acid using heat and anhydrous ZnCl2 as a catalyst and using 10% sodium bicarbonate to neutralize the reaction. The synthetic compounds were diagnosed with some spectral methods such as [UV], [FTIR], [1H NMR] and [13C-{1H}NMR] , in addition to determining the melting and purity levels of the prepared compounds and monitoring the progress of the reactions using TLC thin layer chromatography. The effect of some prepared compounds on the growth of two types of bacterial isolates, known to be resistant to antibiotics, one negative for Gram stain [Gr-ve], which is Pseudomonas aeruginosa, and the second positive for Gram stain [Gr + ve], which is Staphylococcus aurous, were used antibiotics Amoxicillin and Ampicillin. Some of the prepared compounds showed high inhibitory efficacy against the used bacteria in addition, the conformation of prepared compounds at the lower energy level were studied.