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Ferrocenyl chalcones with O-alkylated vanillins: synthesis, spectral characterization, microbiological evaluation, and single-crystal X-ray analysis

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Abstract

O-alkylated vanillin derivatives 2a–f and acetylferrocene react under Claisen–Schmidt conditions, resulting in good-to-high yields of the corresponding ferrocene chalcones 3a–f. None of the resultant compounds 3b–f has been previously described in the literature. All synthesized compounds were characterized by spectral and physical data, whereas two of them, 1-ferrocenyl-3-(4-ethoxy-3-methoxyphenyl)-prop-2-en-1-one (3b) and 1-ferrocenyl-3-(4-buthoxy-3-methoxy-phenyl)-prop-2-en-1-one (3e), were crystalline substances, suitable for single-crystal X-ray analysis, which confirmed undoubtedly their structures. Chalcones 3a–f were tested for their biological activity and demonstrated relatively good in vitro antimicrobial activity towards different strains of bacteria and fungi. The best antibacterial activity is expressed by compounds 3b and 3c, while compound 3d shows the best antifungal activity.

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Acknowledgments

This work was supported by the Ministry of Science and Technological Development of the Republic of Serbia, Projects No. 172034 and 172014.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, University of Kragujevac, Kragujevac, Serbia

    Jovana Muškinja, Adrijana Burmudžija & Zoran Ratković

  2. Department of Biology, Faculty of Science, University of Kragujevac, Kragujevac, Serbia

    Branislav Ranković & Marijana Kosanić

  3. Vinča Institute of Nuclear Sciences, Laboratory of Theoretical Physics and Condensed Matter Physics, University of Belgrade, Belgrade, Serbia

    Goran A. Bogdanović & Slađana B. Novaković

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  1. Jovana Muškinja
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  2. Adrijana Burmudžija
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Correspondence to Zoran Ratković.

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44_2016_1609_MOESM1_ESM.doc

The supplementary Crystallographic data for the structural analysis have been deposited with Cambridge Crystallographic Data Centre: Deposition number CCDC-1407296 and 1407297 for compounds 3b and 3e respectively. These data can be obtained free of charge from The Cambridge Crystallographic Data Center, via www.ccdc.cam.ac.uk/data_request/cif or 12, Union Road, Cambridge, CB2 1EZ, UK; Fax:+44 1223 336033; e-mail: deposit@ccdc.cam.ac.uk).

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Muškinja, J., Burmudžija, A., Ratković, Z. et al. Ferrocenyl chalcones with O-alkylated vanillins: synthesis, spectral characterization, microbiological evaluation, and single-crystal X-ray analysis. Med Chem Res 25, 1744–1753 (2016). https://doi.org/10.1007/s00044-016-1609-8

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