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Microwave-assisted synthesis of derivatives of khellinone under phase-transfer catalytic conditions

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Abstract

The microwave-assisted synthesis of four new 5-acetyl-4,7-dimethoxy-6-hydroxybenzofuran (khellinone) analogs is described. The structures of the obtained derivatives in the solid state are evaluated on the basis of 13C CP/MAS NMR spectra and theoretical calculations at DFT level. A single crystal X-ray diffraction structure is presented for 8-acetyl-7-hydroxy-4-methylcoumarin. 1,4-Bis(5-acetyl-4,7-dimethoxybenzofuran-6-yloxy)butane was evaluated for potential anticancer activity in an in vitro screening panel of 60 human tumor cell lines. Selected leukemia, non-small cell lung cancer, CNS, melanoma, ovarian, and breast cancer cell lines were sensitive to this compound.

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Authors and Affiliations

  1. Department of Organic Chemistry, Faculty of Pharmacy, Medical University of Warsaw, Warsaw, Poland

    Elżbieta Hejchman & Dorota Maciejewska

  2. Department of Crystallography, Faculty of Chemistry, Adam Mickiewicz University, Poznań, Poland

    Irena Wolska

Authors
  1. Elżbieta Hejchman
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  2. Dorota Maciejewska
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  3. Irena Wolska
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Corresponding author

Correspondence to Elżbieta Hejchman.

Additional information

Correspondence: Elżbieta Hejchman, Department of Organic Chemistry, Faculty of Pharmacy, Medical University of Warsaw, Banacha 1, 02-097 Warsaw, Poland.

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Hejchman, E., Maciejewska, D. & Wolska, I. Microwave-assisted synthesis of derivatives of khellinone under phase-transfer catalytic conditions. Monatsh Chem 139, 1337–1348 (2008). https://doi.org/10.1007/s00706-008-0931-3

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  • DOI: https://doi.org/10.1007/s00706-008-0931-3

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