Abstract
Some of the chalcones and flavones are very efficient to facilitate the signal of death to the lung cancer cell through blocking the active site BH3 of Bcl-2 proteins. We designed a number of novel chalcones and flavones targeting the active site of the protein. Docking study showed that the designed compounds were very efficient as the reported compounds. We synthesized and characterized some of the designed compounds. 2,3-Tetrasubstituted-2,3-dihydrobenzofuran-3-carboxamides were generated as novel products by base-catalyzed condensation of o-hydroxyacetophenones and p-nitrobenzaldehyde in different alcohols. Detailed NMR spectroscopic analysis including COSY, homodecoupling and HETCOR (one bond as well as long-range) studies established the structure of the compounds. Mechanistic paths have been suggested for the formation of the novel products.
Graphic Abstract
SYNOPSIS: With the help of structural features of naturally occurring anti-cancer chalcones and flavones, we developed a strategy for the synthesis of some novel chalcones and flavones suitable for inhibiting lung cancer. To check their efficiency for this cancer, we have taken help of theoretical calculations. From docking of the reported and designed compounds with the protein targeted by reported compounds, the synthesis of the designed compounds were encouraged us. We synthesized and characterized a number of designed compounds through the simple synthetic method.
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Acknowledgements
Financial assistance to S. P. Dey from the University Grants Commission, New Delhi for this work is gratefully acknowledged. We are also grateful to the University of Calcutta and Jadavpur University for providing the instrumental facilities.
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NMR data and figures of the compounds and the docking results with different poses of the synthesized compounds with Bcl-2 protein are available at www.ias.ac.in/chemsci.
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Dey, S.P., Sepay, N., Mallik, A.K. et al. Novel chalcones as Bcl-2 inhibitor in lung cancer: docking, design and synthesis of 2,3-Tetrasubstituted-2,3-dihydrobenzofuran-3-carboxamides. J Chem Sci 132, 105 (2020). https://doi.org/10.1007/s12039-020-01812-2
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DOI: https://doi.org/10.1007/s12039-020-01812-2