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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 49, 2019 - Issue 20
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Articles

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

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Pages 2671-2682 | Received 30 Mar 2019, Published online: 16 Jul 2019
 

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).

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