Ligand-assisted click reaction for the synthesis of new hybrid compounds based on 1,2,3-triazoles and 5,5-diphenylimidazolidine-2,4-dione and evaluation of their antibacterial activities

Abstract

The new hybrid compounds based on 1,2,3-triazoles and 5,5-diphenylimidazolidine-2,4-dione were successfully synthesized by copper-catalyzed click reaction in the presence of water-soluble ligand, sodium 4-amino-5-hydroxy-7-sulfonaphthalene-2-sulfonate and copper salt. The click reaction of 5,5-diphenyl-3-(prop-2-yn-1-yl)imidazolidine-2,4-dione and 5,5-diphenyl-1,3-di(prop-2-yn-1-yl)imidazolidine-2,4-dione with aryl azides or sodium azide and benzyl chloride in water produced new 1,2,3-triazoles linked-5,5-diphenylimidazolidine-2,4-dione. The 4-amino-5-hydroxy-7-sulfonaphthalene-2-sulfonate was used as ligand, which enhanced the reactions and reduced the quantity of the toxic copper salt. The in vitro antibacterial activities of the all synthesized compounds were screened against the Gram-positive and Gram-negative bacteria, by the use of well diffusion method. The results showed that all compounds were active against both M. luteus and P. aeruginoasa bacteria.