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Two series of novel multifunctional pyrimidine–imine hybrids were synthesized and evaluated for their antitubercular and antimicrobial properties. A novel synthetic methodology utilizing water as a green solvent and a catalytic amount of HCl resulted in the isolation of barbituric acid – uracil – imine hybrids in moderate to good yields. The in vitro antitubercular activity of the compounds revealed exceptional activity, with D16 showing MIC₁₀₀ at 6 µM, which is comparable to the commercial drug ethambutol with MIC₁₀₀ at 7.63 µM. Compounds D7, D12, D18, D19, and D20 also showed MIC₁₀₀ at concentrations ranging from 10.60 µM to 50.86 µM. The compounds were also noncytotoxic in the mouse macrophage cell line (RAW 264.7) at 25 µg/ml concentration. Molecular docking studies were carried out against M.tb thymidylate kinase to gain insights into the binding modes of the compounds and understand the …