Synthesis, Spectroscopic, Electronic Charge Transfer and Non-covalent Interactions Studies on (E)-5-Bromo-3-((3-chloro-4-fluorophenyl)imino)indolin-2-one: In vitro Studies against the Cancer Cell Lines

This research focuses on synthesising an anticancer drug titled (E)-5-bromo-3-((3-chloro-4-fluorophenyl)imino)indolin-2-one (5BFIO) and validating its analytical values through theoretical and experimental evaluation using techniques such as FT-IR, FT-Raman, 1H and 13C NMR. Moreover, the anticancer activity of 5BFIO molecule was evaluated using molecular docking against cancer proteins (4B55, 5KYG and 6UGR) and 60 human cancer cell lines of NCI-60 under in silico and in vitro analyses, respectively. In the formation of docked complexes, low binding affinities -5.78 for 5BFIO-4B55, -6.72 for 5BFIO-5KYG and -8.86 for 5BFIO-6UGR) were noted in kcal/mol, respectively. Moreover, 5BFIO showed the best activity (49.59% GI) against the MCF7 breast cancer cell line. Density functional theory (DFT) was effectively employed to analyse the molecule’s stability under optimal conditions for comparative studies that incorporate both observational and computational data from gas phases. The outcomes of this study present a comprehensive analysis of gas-phase properties, including nonlinear optical (NLO) behaviour, molecular electrostatic potential (MEP), electron localization function (ELF), localized orbital locator (LOL) and reduced density gradient (RDG) descriptors. The pharmacological evaluation demonstrated significant anticancer activity and it could be derivatized into a more potent drug-like molecule using chemical reactions.