Efficient procedure with new fused pyrimidinone derivatives, Schiff base ligand and its La and Gd complexes by green chemistry

Abstract

In this study, a convenient synthesis of a series of pyrimido[4,5-d]pyrimidine, pyrimidine acetohydrazide, and thieno[3,2-d]pyrimidine-7-carbohydrazide derivatives, via the reactions of versatile, readily accessible electrophilic and nucleophilic reagents with 2-thioxodihydropyrimidine-4,6(1H,5H)-dione 1, is described. Different biologically active moieties such as thiophene and pyridine are introduced in order to investigate their anticancer activity in vitro. In addition, a Schiff base ligand derived from the reaction of 5-bromosalicylaldehyde with 6-aminothieno[3,2-d]pyrimidine carbohydrazide 8 and its La(III) and Gd(III) complexes (in the bulk and at the nanoscale) were prepared and characterized by elemental analyses, IR spectra, magnetic measurement, and electronic absorption data. Chemical shifts of the different types of protons in the NMR spectra of the prepared Schiff base and its metal complexes are also reported. The nanocomplexes were characterized with a scanning electron microscope. The cytotoxicity of all newly synthesized compounds was demonstrated and they were tested for their activity against common pathogenic organisms and anticancer activity against human epithelial colorectal adenocarcinoma cells (Caco2). Some of the newly synthesized compounds had the best recorded anticancer activity against Caco2 cells. In addition, the three active compounds were tested for antibacterial activity. The three structures succeeded in affecting and stopping the growth of Klebsiella pneumoniae strain and the results revealed promising activity.