Synthesis and Antimicrobial Activity of Some New Barbituric Acid Derivatives Containing Thiazole Moiety from Sulfadiazine

A new series of barbituric acid derivatives w prepared and characterized by Fourier-transform infrared spectroscopy (FTIR), proton nuclear magnetic resonance (¹H-NMR) and nuclear magnetic resonance (¹³C-NMR). The antimicrobial studies of synthesized compounds were screened for antibacterial activity against three different types of bacteria (Staphylococcus aureus, Pseudomonas aeruginosa and Escherichia coli), and against two types of fungi (Candida albicans and Aspergillus flavus). In this research, a reaction of sulfadiazine with chloroacetylchloride gave 2-chloro-N-(4-(N-pyrimidin-2-ylsulfamoyl)phenyl)acetamide [A] which was reacted with thiourea, and with K₂CO₃ to give thiazole derivative [B]. The last compound (thiaole derivative) was reacted with chloroacetyl chloride in basic medium to form compound [R]. 5,5-Diethyl barbituric acid and 5-phenyl,5-ethyl barbituric acid were treated with formaldehyde to give 1,3-bis(hydroxyl methyl)barbituric acids derivatives [B₁] and [B₂]. Finally, the compound [R] reacted with 1,3-bis(hydroxyl methyl) barbituric acids derivatives via Williamson reaction to form new barbituric acid derivatives [RB₁] and [RB₂]. By the reaction of 5,5-diethyl barbituric acid with 5-phenyl,5-ethyl barbituric acid, new compounds of barbituric acids derivatives [RB₃] and [RB₄] were obtained. The biological applications of the synthesized compounds showed a greater effect in antimicrobial activities from the starting material (sulfadiazine).