Abstract
Considerable attention has been focused on the [1,3] dipolar cycloaddition reaction approach of olefin with amino acid (sarcosine), and isatin which underwent smoothly, and afforded a highly functionalized complex molecule. The target spiroindolone analogue 4 was synthesized in excellent yield. The desired compound was elucidated based on X-ray single crystal diffraction technique. Compound 4 was examined against three different cancer cell lines for liver, breast and colorectal cancer (HepG2, MCF-7 and HCT-116, respectively). It showed high selectivity against colon cancer (HCT-116). Hirshfeld molecular packing analysis of 4 showed that the H⋯H, Cl⋯H and C⋯H contacts are the most abundant while the N⋯H and O⋯H hydrogen bonding interactions are the strongest. Molecular and electronic structures as well as the Uv–Vis and NMR spectra of 4 were discussed based on DFT calculations. The longest wavelength band observed at 298 nm was assigned for the HOMO-2/HOMO-1→LUMO excitations. The 1H and 13C NMR chemical shifts of 4 were calculated and compared with the experimental data (0.934–0.954).
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•The manuscript involved design of spiroindolone analogue as anti-cancer agent.•The designed compound was assigned by X-ray single crystal.•Anti-proliferative activities of the designed compound were carried out.•Computational studies of the designed compound were investigated.