Design, structural, DFT, Molecular docking studies and biological evaluation of 4-aminiumantipyrine dihydrogenphosphate monohydrate

Abstract Design and supramolecular structural features of the hydrated dihydrogenphosphate salt of 4-aminoantipyrine (4AAPDHP) has been investigated as an ever first report on the literature. The crystals have been grown by the slow evaporation method. Single crystal X-ray diffraction analysis revealed the orthorhombic crystal system with P212121 space group. The N atom of the amino group is connected with O atom of the anion through N–H•••O intermolecular hydrogen bond forming a chain C22(6) motif running along the a- axis of the unit cell. The amino and ketone group of the cation is associated with phosphate anion through N–H•••O and O–H•••O, intermolecular hydrogen bond to form cation-anion dimer ring R22(9) motif. The density functional theory has been carried out at 6-311++G (d,p) level to reach the good agreement between computed and experimental spectra led to a reliable vibrational assignment. HOMO-LUMO energy gap and quantum chemical descriptors values have been calculated. The population of various atoms within the molecules is analyzed using Mulliken charge analysis. The thermal decomposition and thermal stability has been assessed from TG and DTA. Antioxidant activity, cytotoxicity analysis and in-vitro biological properties of the newly synthesized salt have been carried out and the results show the good biological activity. Furthermore, molecular docking studies have been performed.