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Microwave-Assisted Three-Component Domino Synthesis of Polysubstituted 4H-Pyran Derivatives and Their Anticancer Activity

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Abstract

An efficient microwave-assisted one-pot procedure has been proposed for the synthesis of new 4-aryl-6-(methylamino)-5-nitro-2-(1H-pyrrol-2-yl)-4H-pyran-3-carbonitriles by condensation of 3-oxo-3-(1H-pyrrol-2-yl)propanenitrile with (E)-N-methyl-1-(methylsulfanyl)-2-nitroethenamine and substituted benzaldehydes in the presence of a catalytic amount of piperidine using ethanol as a solvent. The transformation occurs via successive Knoevenagel condensation, Michael addition, and intramolecular cyclization. The proposed procedure is advantageous due to its one-pot mode, short reaction time, simple purification by recrystallization, and excellent yields. The product structure was confirmed using various spectroscopic techniques, including IR,1H and 13C NMR, LC/MS, elemental analysis, and single crystal X-ray diffraction study. The synthesized compounds were evaluated for their anticancer activity against 60 different human cancer cell lines in nine cancer panels, and two compounds were found to be potent against different cell lines.

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ACKNOWLEDGMENTS

The authors are thankful to the Department of Chemistry (UGC-SAP, FIST sponsored), Saurashtra University, Rajkot, for providing the laboratory facilities and National Facility for Drug Discovery Complex (NFDD), Centre of Excellence (CoE) and School of Science, Department of Chemistry, RK University, Rajkot (Gujarat), India, for providing the spectral data. The authors are also thankful to the National Cancer Institute, a part of the National Institute of Health (NIH).

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Authors and Affiliations

  1. School of Science, Department of Chemistry, RK University, 360020, Rajkot, Gujarat, India

    S. D. Hadiyal & J. N. Lalpara

  2. Department of Chemistry, Saurashtra University, 360005, Rajkot, Gujarat, India

    N. D. Parmar, P. L. Kalavadiya & H. S. Joshi

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  1. S. D. Hadiyal
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  2. N. D. Parmar
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  3. P. L. Kalavadiya
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Correspondence to H. S. Joshi.

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Hadiyal, S.D., Parmar, N.D., Kalavadiya, P.L. et al. Microwave-Assisted Three-Component Domino Synthesis of Polysubstituted 4H-Pyran Derivatives and Their Anticancer Activity. Russ J Org Chem 56, 671–678 (2020). https://doi.org/10.1134/S1070428020040168

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  • DOI: https://doi.org/10.1134/S1070428020040168

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