Synthesis of highly functionalized imine-containing halogen-substituted-1-oxo-acenaphthenes and their quantum computational investigation as propitious drugs for anti-skin cancer

Herein, the one-keto protected and one-keto transformed into the imine-functionalized Schiff bases (7a–b) through the 1,2-dimethoxy-1,2-dihydroacenaphthylene using calcium oxo-chloride are reported. However, the analytical techniques named UV–Vis, FT-IR_ν, ¹H, ¹³C NMR, HRMS were used for the characterization, and their analytical values were also validated through the density function theory. Actually, the experimental FT-IR_ν spectra collocated with theoretically illustrated spectra utilizing Potential Energy Distribution (PED) and Frontier Molecular Orbitals (FMO). Moreover, Molecular Electrostatic Potential (MEP) plots in methanol, DMSO, and gas phase provided insights into the electrostatic potential distribution, facilitating the prediction of the molecules’ reactivity. Similarly, the GIAO method was conducted to compare the theoretical ¹H and ¹³C NMR chemical shift values with the experimentally obtained results as well. On the contrary, in-vitro analysis of the anticancer activity of 7a–b against 60 human cancerous cells through the National Cancer Institute Developmental program-USA was evaluated at 10^–5 M concentrations. As per lead molecule, the synthesized 7a compound not only showed 100 % GI but also 42 % lethality for the MDA-MB-435 of melanoma cancer cell. Moreover, molecular docking as artificial intelligence tool was used for the formation of docked complexes, including MN1R-7a, MN1R-7b, and MN1R-Decarbazine, and consequently they showed −8.79, −7.67, and −6.51 binding affinities in Kcal/mol units, respectively. Further, the stability of docked complexes and their physical parameters, including RMSD, RMSF, SASA, ΔGsolv, Rg values, and hydrogen-bond analysis, were performed. Futuristically, synthesized compound 7a could be used for further analysis, like in-vivo clinical trials, to find their side effects on human cells.