Spectroscopic Identifications, Molecular Docking, Neuronal Growth and Enzyme Inhibitory Activities of Steroidal Nitro Olefin: Quantum Chemical Study

Abstract

AbstractFT‐IR, NMR and ultraviolet spectroscopy by means of DFT / B3LYP‐6‐311G(d, p), molecular docking and biological activity of 6‐nitrocolest‐5‐en‐3‐beta‐yl acetate (steroid nitro‐olefin) was reported in this article. The optimized molecular geometric structure and its associated parameters including vibrational frequencies, carbon and 1H NMR data of the title compound in ground electronic state was obtained at DFT approach applying B3LYP/6‐311G(d,p). The ultraviolet absorbance data is obtained at TDB3LYP/6‐311G(d,p) basis set. The present computational data are found in reasonable agreement with the experimental results. Simulated electronic and NMR (1H and 13C) spectra have been reported in solution phase. Parameters like thermodynamic quantities, dipole moment, FMO energies, MEP and global reactivity descriptors of steroid nitro olefin were determined at same level of theory. The neuromodulatory effect of the compound on central nervous system development of rat embryonic hippocampal neurons has been studied. Based on the outcome; compound demonstrated suppression activity despite the promotion of neuronal cytoarchitecture leading to a negative effect on hippocampal neurons. The nature of the compound found to be toxic to the cells. Besides, steroid compound is also used to perform inhibitory activity against acetylcholinesterase (AChE) compared to the reference drug i. e. Galanthamine. The molecular docking of the synthesized compound is carried out with the structure of the acetylcholinesterase (PDB: 1DX6) protein to check the mode of interactions.