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Study of the Schiff Base to Enamine-Ketone Rearrangement upon Condensation of Formyl Functionalized 2-Oxaindane Series Spiropyran with Aliphatic Amines

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Abstract

This work focuses on the formyl derivative of 2-oxaindane series spiropyran under its condensation reaction. The data indicated that all products are thermodynamically stable enamine-ketone tautomeric form in both DMSO solution and solid state. This finding can be explained by the migration of proton in 7-hydroxy group to the azomethine nitrogen, which is conjugated with electrocyclic opening of the spirounit in the non-stable Schiff-bases. We observe the enamine-ketones dynamic equilibrium of Z-, E-isomers in the DMSO solution. X-Ray diffraction study was performed for single crystalline sample of aminoethanol derivative. The synthesized compounds were evaluated in vitro cytotoxic activity against four typical human cell lines, showing moderate activity against lung carcinoma (LU-1), hepatocellular carcinoma (Hep-G2), breast carcinoma (MCF-7), and undifferentiated thyroid carcinomas (8505c). Among them, the compound with R = i-Pr showed the best activity with IC50 values 10.60 (MCF-7), and 10.55 µM (8505c). The in vitro antioxidant activity test using 1,1-diphenyl-2-picrylhydrazyl (DPPH) showed that all the synthesized compounds have weak or no activity.

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ACKNOWLEDGMENTS

Spectral study was performed using the equipment of Joint Resource Centre “Molecular Spectroscopy”, DFT calculations were performed at JRC “High-performance calculations” of Southern Federal University.

Funding

This work was financially supported by Russian Foundation for Basic Research (project no. 21-53-54007) and the Vietnam Academy of Science and Technology (subject code QTRU01.08/21-22).

Author information

Authors and Affiliations

  1. Department of Chemistry, Southern Federal University, 344019, Rostov-on-Don, Russia

    X. T. Nguyen, A. O. Bulanov, V. V. Lukov & I. N. Shcherbakov

  2. Institute of Chemistry, Vietnam Academy of Science and Technology, 100000, Hanoi, Vietnam

    X. T. Nguyen

  3. Institute of Physical and Organic Chemistry, Southern Federal University, 344090, Rostov on Don, Russia

    G. Borodkin

  4. Institute for Tropical Technology, Vietnam Academy of Science and Technology, 100000, Hanoi, Vietnam

    T. T. T. Nguyen, L. D. Tran & B. N. Duong

  5. Hanoi University of Science and Technology, 100000, Hanoi, Vietnam

    H. D. Vu

  6. Office of the State Council for Professorship, Ministry of Education and Training, 100000, Hanoi, Vietnam

    B. N. Duong

  7. National Research Center “Kurchatov Institute”, 123182, Moscow, Russia

    V. A. Lazarenko

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  1. X. T. Nguyen
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  2. A. O. Bulanov
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  9. V. A. Lazarenko
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  10. I. N. Shcherbakov
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Correspondence to A. O. Bulanov.

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Nguyen, X.T., Bulanov, A.O., Lukov, V.V. et al. Study of the Schiff Base to Enamine-Ketone Rearrangement upon Condensation of Formyl Functionalized 2-Oxaindane Series Spiropyran with Aliphatic Amines. Russ J Gen Chem 93, 215–226 (2023). https://doi.org/10.1134/S1070363223010267

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