Microwave assisted green synthesis, Single crystal XRD, DFT, Hirshfeld surface analysis, Antibiofilm, Anti-inflammatory activity and Molecular docking study of 4-(4-Fluorophenyl)-5-methyl-1,3-thiazole-2-amine

Abstract

The title compound 4-(4-Fluorophenyl)-5-methyl-1,3-thiazole-2-amine was synthesized by the green microwave irradiation method and the structure was confirmed by spectroscopic techniques. Single crystal X-ray diffraction study was performed to investigate the crystal structure of the title compound. Further, the molecular structure was optimized by density functional theory (DFT) calculations using the B3LYP/6-311G++ (d, p) basic set and compared with X-ray diffraction data. DFT optimized structure, geometrical parameters and IR spectra of the title compound showed excellent correlations with the experimental results. The chemical reactivity and stability of the title compound were studied by molecular electrostatic potential (MEP) and Frontier molecular orbitals (FMOs) analysis. Intermolecular interactions of the title compound were analyzed by Hirschfeld surfaces and 2D-fingerprint plots. In vitro, antibiofilm activity against C. albicans, suggests a potential biofilm inhibitor (MIC 12.5 μg/ml). A molecular docking study of the title compound with the active sights of the target protein (PDB:5TZ1) justifies the results of the antibiofilm activity whereas a drug-likeness pharmacokinetic study is used to analyze the safety and efficiency of the drug. Furthermore, the Anti-inflammatory activity study of the title compound indicates significant (82.63%) inhibition of protein denaturation.