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Copper(II) Complex of Bis(1',3'-Hydroxymethyl)-Spiro-(Fluorene-9,4'-Imidazolidine)-2',5'-Dione, Cytotoxicity and Antibacterial Activity of Its Derivative and Crystal Structure of Free Ligand

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Abstract

The aims of the present study were to synthesize, elucidate the structure and investigate the biological properties of substituted fluorenylspirohydantoins: Cu(II)L1 complex of 1,3-dihydroxymethyl-(9'-fluorene)-spiro-5-hydantoin (bis(1',3'-hydroxymethyl)-spiro-(fluorene-9,4'-imidazolidine)-2',5'-dione) (L1) and 4'-bromo-(9'-fluorene)-spiro-5-hydantoin (4'-bromо-spiro-(fluorene-9,4'-imidazolidine)-2',5'-dione) (L2). Based on the experimental data, the most probable structure for the copper(II) complex was suggested with one deprotonated OH group in C-7 position of two ligand L1 molecules and O4-atom and formed six-membered chelate rings CuOCNCO–[CuL1-H)2]. We determined their cytotoxic effects on the tumor human cell line A2058 by WST-1 assay (Roche Applied Science). The antimicrobial activity against both Gram-positive, Gram-negative bacteria and the yeast Candida albicans was studied additionally. The structures of the new compounds were discussed based on the performed spectroscopic measurements (UV-Vis, IR, Raman, 1H- and 13C NMR spectroscopy) and the single-crystal X-ray diffraction method for 1,3-dihydroxymethyl-(9'-fluorene)-spiro-5-hydantoin. The compound was crystallized in monoclinic crystal system and P21/c space group.

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ACKNOWLEDGMENTS

We are grateful also to prof. Plamen Penchev from University of Plovdiv for spectra measurements.

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Authors and Affiliations

  1. University of Plovdiv, Faculty of Chemistry, Department of General and Inorganic Chemistry with Methodology of Chemistry Education, 4000, Plovdiv, Bulgaria

    P. Marinova

  2. Agricultural University, Faculty of Plant Protection and Agroecology, Department of Chemistry and Phytopharmacy, 4000, Plovdiv, Bulgaria

    M. Marinov

  3. Medical University-Plovdiv, Department of Medical Biology, 4000, Plovdiv, Bulgaria

    M. Kazakova, Ya. Feodorova & V. Sarafian

  4. Research Institute at Medical University of Plovdiv, 4000, Plovdiv, Bulgaria

    M. Kazakova, Ya. Feodorova & V. Sarafian

  5. University of Food Technologies, Department of Microbiology, 4002, Plovdiv, Bulgaria

    D. Blazheva & A. Slavchev

  6. University of Plovdiv, Faculty of Biology, Department of Biochemistry and Microbiology, 4000, Plovdiv, Bulgaria

    D. Georgiev

  7. University of Ruse—Razgrad Branch, Department of Chemical, Food and Biotechnologies, 7200, Razgrad, Bulgaria

    I. Nikolova & N. Stoyanov

  8. Institute of Mineralogy and Crystallography, Bulgarian Academy of Sciences, 1113, Sofia, Bulgaria

    H. Sbirkova-Dimitrova

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Marinova, P., Marinov, M., Kazakova, M. et al. Copper(II) Complex of Bis(1',3'-Hydroxymethyl)-Spiro-(Fluorene-9,4'-Imidazolidine)-2',5'-Dione, Cytotoxicity and Antibacterial Activity of Its Derivative and Crystal Structure of Free Ligand. Russ. J. Inorg. Chem. 66, 1925–1935 (2021). https://doi.org/10.1134/S0036023621130052

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