Introduction. Bridged 1,3-diazine systems attract considerable interest in organic and medicinal chemistry. At the same time, Schiff bases are of particular interest to researchers as effective complexing agents for various ions. There is no doubt that bridged 1,3-diazine systems potentially possess a sufficiently broad spectrum of biological activity. Therefore, the synthesis and study of novel azomethine systems based on pyrimidines represents a highly promising research direction, as it opens possibilities for obtaining new biologically active compounds.
Material and methods. The aim of our work was the synthesis of novel bridged systems based on 4,6-dihydroxypyrimidine-5-carbaldehydes. A series of bisazomethines was obtained through the nucleophilic addition reaction of m- and p-phenylenediamines to the carbonyl group of
4,6-dihydroxypyrimidine-5-carbaldehydes. During the synthesis of target compounds, methanol and water were used as solvents, with practical yields being comparable under these conditions. The structures of the target compounds were confirmed by ¹H and ¹³C NMR spectroscopy.
Results. According to in silico screening data using web resources PASS-online, CLC-pred, Antivir-pred and GUSAR-online, the synthesized bisazomethines demonstrate a broad spectrum of biological activity (antibacterial, antifungal and antiviral), and are classified as Class 4 toxicity according to the OECD project classifier.
Conclusion. Thus, a series of novel bridged bisazomethines based on 5-formyl derivatives of pyrimidine-4,6-diols was obtained, exhibiting both a high safety profile and promising types of biological activity. The newly synthesized bisazomethines are also of great interest as unique ligands for the preparation of transition metal complexes, which potentially have high prospects for pharmaceutical applications.