A New Schiff Base Molecule Prepared from Pyrimidine-2-thione: Synthesis, Spectral Characterization, Cytotoxic Activity, DFT, and Molecular Docking Studies

Abstract

Schiff base derivatives are some of the most widely used organic compounds for industrial purposes and they exhibit a broad range of biological activities. In this paper, a new Schiff base derivative (2) synthesized from the condensation reaction of 1-amino-5-benzoyl)-4- phenylpyrimidine-2(1H)-thione (1) with 2-chlorobenzaldehyde. The new compound was characterized by 1H, 13C NMR, and FT-IR. The biological activity property of this compound was tested against two different cancer cell lines and a healthy human cell line. The results demonstrate that molecule 2 has antiproliferative activity. In molecular modeling studies, the interaction site was examined using the epidermal growth factor receptor (EGFR) tyrosine kinase domain. Alignment in molecular docking, surface mapping binding, amino acids, and binding energy calculated. Glide score energy was found to be -9.820 kcal/mol and it predicted that the bonding interaction is strong. Theoretical calculations were made to compare the experimental and theoretical data. These calculations were performed on the 6–31 G* basis set using the Density Functional Theory (DFT) method and Becke-3-Parameter-Lee-Yang-Parr (B3LYP). Using this method, various parameters, such as frontier molecular orbitals, HOMO-LUMO energy levels, band gap, and chemical reactivity indices were found and interpreted.

Keywords

• Cytotoxic activity
• Pyrimidine-2-thione
• 2-Chlorobenzaldehyde
• Schiff Base
• Synthesis
• Molecular Docking

References

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