Spectroscopic, electronic properties analysis for 2, 6-Bis (phenylamino)-4-(iminophenyl) benzoquinone molecule and molecular docking clarification for its anticancer activity detected by strong inhibition of NQO1 enzyme

• Published in: Journal of molecular structure 2023-06, Vol.1282, p.135231, Article 135231
• Main Authors: Abbas, Faheem, Attia, Mohamed I, Alghamdi, Suzan K., Khouqeer, Ghada A., Hussein, Rageh K.
• Format: Article
• Language: English
• Subjects: ADMET; DFT; Molecular docking; Quinone compound; UV-Vis
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2023.135231

•This work discuss the investigation of the spectroscopic data (IR, UV-Vis), and HOMO-LUMO, MEP, NLO, NBO analysis and the antifungal activity of a previously synthesized novel pyrimidine molecule “2, 6-Bis (phenylamino)-4-(iminophenyl) benzoquinone".•Density functional theory, ADMET and molecular docking were used as investigated techniques.•Chemically, the molecule was found to stable. The DFT analysis revealed reactive regions and the charge density distributions within the molecule that could be linked to biological activity.•The molecule contains safety agents and has been validated as a pharmaceutical drug by drug likeness and ADMET analysis•The molecule binding to NQO1 receptor protein with superior binding energy −8.69 kcal/mol.•The molecule has a potential anticancer drug due to its high capability to inhibit the NQO1 enzyme. Quinone compounds have been the subject of extensive research due to their remarkable efficiency and prospective use as drugs and in a variety of fields. In this study, we report the spectroscopic characterization, electronic structure, ADMET evaluation, and molecular docking assessment of 2,6-Bis(phenylamino)-4-(iminophenyl)benzoquinone as an anticancer drug. By using DFT investigations, the vibrational wavenumbers were calculated and utilized to assign vibrational bands, which were found to be in good accordance with the experimentally observed data. The analysis of the UV-Vis spectra revealing an absorption peak from electronic transitions HOMO→LUMO at 547 nm is found to be in good conformity with its experimental value. The HOMO and LUMO frontier molecular orbitals and their associated energies highlighted the mechanism of charge transfer within the molecule and revealed a small energy gap. The chemically reactive sites identified by the MEP surface helped predict the spots of the molecule's biological activity. According to NBO analysis, the π C9-C10 → π* C11-C12 interaction has the maximum energy stability with 23.74 Kcal/mol., due to π electron delocalization within the ring. At the same level of theory, third-order NLO polarizability was found to be 4-fold stronger than the third-order of P-NA (a prototype NLO molecule). The potential for a safe oral bioavailability drug was identified by computing ADMET parameters and evaluating drug-likeness based on Lipinski's rule of five. The molecular docking study found that the molecule binding to NQO1 receptor protein with superior binding energy -8.69 kcal/mol than previousl