Design, Synthesis and Biological Evaluation of 4-Hydroxy-2-Thioxo-4-Trifluoromethyl-Hexahydro-Pyrimidin-5-yl]-p-Tolyl-Methanone Derivatives as Potent Anti-Inflammatory and Antimicrobial Agents

Abstract

A series of new 4-hydroxy-2-thioxo-4-trifluoromethyl-hexahydro-pyrimidin-5-yl]-p-tolyl-methanone derivatives were synthesized through one-pot three-component method using 4,4,4-trifluoro-1-p-tolyl-butane-1,3-dione, thiourea, and various substituted benzaldehydes. The structures of newly synthesized products were elucidated by spectroscopic studies such as IR, NMR (proton and carbon), mass spectra, and elemental analyses. The final products were screened for their antioxidant activity, anti-inflammatory activity against LPS-induced cell death in RAW 264.7 macrophage cell lines, antibacterial and antifungal activity using in vitro methods. The results revealed that the compounds such as 10e and 10i against DPPH and H₂O₂; 10a, 10e, 10h, and 10i against LPS induced inflammation in RAW 264.7 cell lines; 10a, 10b, 10c, 10d, and 10e against all the microbial strains tested have exhibited higher content of activity in vitro than the rest of the title compounds when compared to the standard drugs. In overall, 10a, and 10e have shown the most promising activity against all the systems tested. Hence, among all the title compounds, at least a few will stand as next generation antioxidant, anti-inflammatory and antimicrobial agents in future.