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Enaminoketones: Functional Derivatives Based on 7-Hydroxy-3′,3′-dimethyl-3′H-spiro[chromen-2,1′-isobenzofuran]-8-carbaldehyde with Aromatic Amines. Physicochemical Studies and Biological Activity

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Abstract

The derivatives of the 2-oxaindane series spiropyran (7-hydroxy-3′,3′-dimethyl-3′Н-spiro[chromene-2,1′-isobenzofuran]-8-carbaldehyde) series have been synthesized via its condensation with aromatic amines. The obtained compounds have existed as enaminoketones in the solution as well as in the solid state. Dynamic equilibrium of the E,Z-isomers has been observed in the solutions of the obtained derivatives in DMSO. The structure of the enaminoketone based on 3,4-dimethylaniline has been confirmed by means of X-ray diffraction analysis. The in vitro cytotoxic activity of the synthesized compounds has been investigated. Moderate activity towards the cells of hepatocellular human carcinoma (HepG2), breast carcinoma (MCF-7), lung cancer (A549), and carcinoma (KB) has been revealed. The anticancer activity of the prepared enaminoketones has been assessed by means of molecular docking.

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Funding

This study was performed with financial support from the Russian Foundation for Basic Research and Vietnam Academy of Science and Technology (project no. 21-53-54007, topic code QTRU01.08/21-22) using the equipment of the Joint Resource Center “Molecular Spectroscopy” and the Center for Collective Usage “High-Performance Calculations” of Southern Federal University.

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Authors and Affiliations

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

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

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

    X. T. Nguyen

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

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

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

    H. D. Vu

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

    B. N. Duong

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

    V. A. Lazarenko

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  1. X. T. Nguyen
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Nguyen, X.T., Zantman, A.A., Bulanov, A.O. et al. Enaminoketones: Functional Derivatives Based on 7-Hydroxy-3′,3′-dimethyl-3′H-spiro[chromen-2,1′-isobenzofuran]-8-carbaldehyde with Aromatic Amines. Physicochemical Studies and Biological Activity. Russ J Gen Chem 93, 1028–1039 (2023). https://doi.org/10.1134/S1070363223050031

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