Synthesis, crystal structure, theoretical chemical activitiy, electrophilicity-based charge transfer (ECT) with DNA bases and molecular docking studies of 2-amino-4-(2,4-dimethoxyphenyl)-5,6-dihydrobenzo[H]quinoline-3-carbonitrile

Abstract

In this study, the title compound is synthesized and characterized by X-ray diffraction method, FT-IR, UV–Vis, TGA and NMR spectroscopy. The crystal packing is mainly controlled by N–H…N, C–H…N hydrogen bonds and C–H…π interactions. Hirshfeld surface analysis reveals the presence of intermolecular interactions in the crystal. All theoretical computations (NBO, FMOs, MEP, FF, ECT) are calculated by Density Functional Theory (DFT) at B3LYP level by using 6–311G(d,p) basis set. The stability of the molecule arising from hyperconjugative interactions, charge delocalization was analyzed by using natural bond orbital analysis (NBO). Also, the interactions between the title molecule and DNA bases are investigated by using the ECT (electrophilicity-based charge transfer) method. Calculations show that the title molecule interacts with the guanine more than other DNA bases. Furthermore, the interactions states between the guanine DNA (PDB:4ENM) and the studied molecule is determined by molecular docking study.