Synthesis, spectra, electronic structure, molecular docking and cytotoxicity investigation on 2-(piperidin-1-ylmethyl)-isoindoline-1,3-dione - A Mannich base system

A Mannich base molecule of 2-(piperidin-1-ylmethyl)isoindoline-1,3-dione (PPF) has been synthesized using Mannich base condensation reaction. The molecular geometry of PPF molecule was optimized by B3LYP/6-311G(d,p) basis set. The vibrational frequencies have been assigned with the aid of normal coordinate analysis. Total energy distributions (TED) were used to explain each vibrational wavenumber assignments of a molecule. The H-1 and C-13 NMR spectroscopic analyses were predicted by using gauge independent atomic orbital (GIAO) method. The thermal stability was determined by applying the thermo gravimetric/differential scanning calorimetry (TG/DSC) studies. The HOMO-LUMO energies, population density of states (PDOS), overlap population density of states (OPDOS), reduced density gradient (RDG), Mulliken atomic charges and molecular electrostatic potential (MEP) surface were plotted to investigate the van der Waals, attraction, repulsion, non-covalent and covalent interactions of the compound. The natural bond orbital (NBO) charge analysis was used in explaining the intermolecular charge transfer and resonance stabilization energy of molecule. Besides, the molecular docking studies have been performed. The cytotoxic activity of the PPF molecule has been resolved. (C) 2020 Elsevier B.V. All rights reserved.

Automated summary

A Mannich base molecule of PPF was synthesized and characterized in terms of molecular geometry, vibrational frequencies, thermal stability, NMR spectroscopic analyses, and various computational methods were used to study the interactions and charge transfer between molecules. Additionally, molecular docking studies were performed to investigate the cytotoxic activity of PPF.