Synthesis, characterization, crystal structure and urease-inhibition activities of three 2-phenylthiazole derivatives

Three 2-phenylthiazole derivatives were synthesized, characterized and evaluated as urease inhibitors. The structures of the 2-phenylthiazole derivatives were characterized by FT-IR, 1H NMR and 13C NMR spectroscopy. Their crystal structures were also determined by single-crystal X-ray diffraction studies. Hirshfeld surfaces analysis and their associated two dimensional fingerprint plots of compounds were used as theoretical approach to assess driving force for crystal structure formation via the intermolecular interactions in the crystal lattices of synthesized compounds. The study of X-ray single crystal diffraction and Hirshfeld surfaces analysis of the prepared compounds shows NH⋯O hydrogen bonds and CH⋯O intermolecular interactions among molecules of synthesized compounds. The urease-inhibition activities of the synthesized compounds were tested by phenol red method. Among the three compounds, the compound N-cyclohexyl-2-(4-methoxyphenyl)thiazole-4-carboxamide (5b) showed the best urease inhibitory activity with the IC50 of 1.82 μM. The docking study performed demonstrated that compound N-cyclohexyl-2-(4-methoxyphenyl)thiazole-4- carboxamide could interact with the catalytic active site of urease.