Synthesis of spirooxindoles promoted by the deep eutectic solvent, ZnCl₂+urea via the pseudo four-component reaction: anticancer, antioxidant, and molecular docking studies

Abstract

Various spirooxindoles (7a–c, 8a–c, 9a–c, and 10a–c) were efficiently synthesized using deep eutectic solvent ZnCl₂+urea and well characterized using IR, ¹H NMR, and ¹³C NMR spectroscopic techniques. The biological screening results showed that the compound 9a exhibited potent anticancer activity against MCF7 and HeLa cell lines with IC₅₀ values 6.47 ± 0.01 and 9.14 ± 0.32 µM, respectively. The compound 7c exhibited potent activity against the HeLa cell line with IC₅₀ value 6.81 ± 0.01 µM. The compound 9a exhibited a potent antioxidant activity with IC₅₀ value 7.34 ± 0.17 µM. The comparative molecular docking study against the cancer proteins EGFR and HER2 revealed that the EGFR was the best target protein receptor for the target compounds. Among all the compounds, the compound 9a exhibited the least binding energy −10.72 kcal/mol against the protein EGFR (PDB ID: 4HJO).

GRAPHICAL ABSTRACT

KEYWORDS:

• Anticancer activity
• antioxidant activity
• deep eutectic solvent
• molecular docking studies
• spirooxindoles