Dual-Function Heterocyclic Phosphonates: Luminescent Scaffolds for Butyrylcholinesterase Inhibition

The synthesis and investigation of a new series of heterobicyclic phosphonates obtained via the reaction of dihydropyrimidine derivatives are reported. The target thiazolo[3,2-a]pyrimidine phosphonates were synthesized selectively in high yields. The structures of all synthesized compounds were confirmed by 1H, 13C, and 31P NMR spectroscopy as well as high-resolution mass spectrometry. Evaluation of the biological activity of the synthesized phosphonates demonstrated that all compounds exhibit inhibitory activity toward butyrylcholinesterase in the millimolar concentration range. The synthesized compounds were also found to possess luminescent properties, enabling not only interaction with the biological target but also real-time monitoring of this process, thereby significantly expanding their potential applications in medicinal chemistry. The obtained results indicate that the synthesized heterobicyclic phosphonates represent promising candidates for further investigation.