Synthesis, crystal and molecular structure, DFT, vibrational spectroscopic, hirshfeld surfaces analyses and molecular docking of a novel compound N-(3-((1-(5-bromo-2-(pyrrolidin-1-yl)phenyl)-5-oxo-[1,2,4]triazolo[4,3-a]quinazolin-4(5H)-yl)methyl)phenyl)-2-thiomorpholinoacetamide

Abstract

The N-(3-((1-(5-bromo-2-(pyrrolidin-1-yl)phenyl)-5-oxo-[1,2,4]triazolo[4,3-a]quinazolin- 4(5H)-yl)methyl)phenyl)-2-thiomorpholinoacetamide is a novel compound having the [1,2,4]triazolo[4,3-a]quinazolinone. It was synthesized by nine steps and confirmed by 13C NMR, 1H NMR, FT-IR and MS spectroscopies. Meanwhile, the single crystal of the title compound was subjected to crystallographic analysis and conformation determination. Moreover, density functional theory (DFT) was used to calculate the optimized structures of the molecule, which was compared with the X-ray measurement. The result of the molecular structure optimized by DFT is similar to the crystal structure determined by X-ray single crystal diffraction. In order to further investigate some physical properties of the title compound, by using the B3LYP/6-311+G(2d, p) method, molecular electrostatic potential and frontier molecular orbitals was calculated. Furthermore, the binding mode of the title compound and SHP2 protein (PDB: 6BMR) was analyzed by molecular docking. Finally, hirshfeld surfaces analyses can explain the atom pair contacts of the crystal and the quantitative analysis of intermolecular interactions.