Synthesis of spirooxindoles promoted by the deep eutectic solvent, ZnCl2+urea via the pseudo four-component reaction: anticancer, antioxidant, and molecular docking studies. Issue 20 (18th October 2019)

• Record Type: Journal Article
• Authors: Nishtala, Venkata Bharat; Gandamalla, Durgaiah; Yellu, Narsimha Reddy; Basavoju, Srinivas
• Is Part Of: Synthetic communications. Volume 49:Issue 20(2019)
• Page Start: 2671
• Page End: 2682
• Publication Date: 2019-10-18
• Subjects: Anticancer activity -- antioxidant activity -- deep eutectic solvent -- molecular docking studies -- spirooxindoles; Organic compounds -- Synthesis -- Periodicals; Chemistry, Organic; Synthesis; 547.205
• DOI: 10.1080/00397911.2019.1639193
• Languages: English
• ISSNs: 0039-7911

Abstract

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, 1 H NMR, and 13 C 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: