Synthesis, Fluorescence Properties, Molecular Docking Studies, and Analysis of the Crystalline Structure of the Novel 5-Imino-7-Aryl-5 H-Thiazolo[3.2-a]Pyrimidine-6-Carbonitrile and Its Derivatives

This study describes a simple, inexpensive, and effective method for the synthesis of new 5-imino-7-aryle-5H-thiazolo[3,2-a]pyrimidine-3-carbonitrile derivatives 4a-e using a green procedure that does not require the use of heat or a base, creating a strategy that meets both economic and environmental demands. Various synthesized products were characterized via diverse techniques such as ¹H-NMR, infrared (FT-IR), Mass spectroscopy (MS), and single crystal X-ray diffraction. Using a fluorescence spectrometer, the 5-imino-7-phenyle-5H-thiazolo[3.2-a]pyrimidine-3-carbonitrile 4a has been tested as a potent fluorescent agent in mixture of DMSO/Water at 10⁻⁴ M in one hand, and on the other hand the results of our fluorescence evaluation studies with metal ions (Pb(II), Ba(II), Cd(II), Ni(II), Mn(II), Hg(II), Zn(II), Fe(II), Co(II), Cu(II), La(II), Cr(III), and Fe(III)) have shown that this compound exhibits a turn-on and turn-off of the fluorescence to 4a compound with these metals, what forms poor to good interaction by these ions. This result represents the emergence of a new potential ligand for the two heavy cations Cd(II) and Pb(II), which are toxic and polluting, and whose detection is currently of high interest. As well, In the molecular docking evaluation study, it was determined that the 4e molecule has an exceptional ability to inhibit the binding energy of the tubulin protein by −9.13 kcal/mmol, compared to other compounds. The results demonstrate the possibilities for a novel oral medication application.