Synthesis, quantum chemical study, AIM simulation, in silico ADMET profile analysis, molecular docking and antioxidant activity assessment of aminofuran derivatives

Abstract

Abstract Quantum computational investigations and in silico biological evaluation of substituted aminofuran derivatives are described in this study. The synthesized compounds were characterized by 1H NMR, 13C NMR, FTIR, UV–Vis and ESI-MS spectroscopic techniques. Experimental observations were compared with the theoretical data generated by quantum chemical calculations. Computational quantum chemical evaluations were done through ab-initio density function theory (DFT) using Becke’s three parameters hybrid functional (B3LYP) with 6–311++G(d,p) level of theory, to study the molecular structural, thermodynamic, nonlinear optical (NLO) and natural bond order (NBO) properties. NBO exploration was also done to study the intermolecular interactions and their stabilization energies with the help of a molecular electrostatic potential map (MEP). Mulliken population and NBO correlated the charge distributions within the molecule. Topological parameters at the bond critical point (BCP) were studied by the quantum theory of atoms in molecules (QTAIM). VEDA4 program was used to evaluate the potential energy distribution (PED). The molecular docking investigation was done with three human targets viz. coronin 1C (Cor1C), eukaryotic elongation factor 1A (eEF1A) and villin found in various carcinoma cells. The molecular docking results of the compounds revealed a good interaction profile with cytoskeletal targets Furthermore, pharmacological absorption, distribution, metabolism, excretion and toxicity (ADMET) properties along with druglikeness were also assessed. The synthesized compounds were also evaluated for their antioxidant activity and were shown to possess potential antioxidant activity.