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Synthesis and biological screening of a new series of 5-[4-(4-aryl-1-piperazinyl)butoxy]coumarins

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Abstract

A series of 5-[4-(4-aryl-1-piperazinyl)butoxy]coumarins were synthesized using microwave-assisted methods. The synthesized compounds were screened for their antibacterial activities against Gram-positive bacterial strains (Staphylococcus aureus, Micrococcus luteus, Bacillus cereus, Bacillus subtilis, Staphylococcus epidermidis, and Enterococcus hirae), Gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa), and for their antifungal activities against three species of Candida (Candida albicans and Candida parapsilosis). The 4,7-dimethyl-5-[4-(pyridin-4-yl)butoxy]coumarin and the 6-acetyl-4,7-dimethyl-5-[4-(pyridin-4-yl)butoxy]coumarin were the most active against the Gram-positive bacteria. The best minimum inhibitory concentration values were obtained for the 4,7-dimethyl-5-[4-[4-[1-(4-pyridyl)]piperazin-1-yl]-butoxy]coumarin against Micrococcus luteus (15 µg/cm3). Two tested compounds exhibited moderate to good antifungal activity. The antitumor activity against of the newly synthesized compounds was evaluated. Among all the compounds tested, the 6-acetyl-4,7-dimethyl-5-[4-[4-(2-fluorophenyl)piperazin-1-yl]butoxy]coumarin was the most potent against HeLa cancer cells. Crystals of 4,7-dimethyl-5-[4-[4-(2-fluorophenyl)piperazin-1-yl]butoxy]coumarin were investigated using a single crystal X-ray diffraction technique.

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Acknowledgments

This project was supported by Medical University of Warsaw, Faculty of Pharmacy, 2014/2015, FW24/NM1/14. The X-ray structure was determined in the Advanced Crystal Engineering Laboratory (aceLAB) at the Chemistry Department of the University of Warsaw.

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Authors and Affiliations

  1. Department of Organic Chemistry, Faculty of Pharmacy, Medical University of Warsaw, 1 Banacha Str., 02 097, Warsaw, Poland

    Kinga Ostrowska, Dawid Grzeszczuk & Dorota Maciejewska

  2. Centre of Biostructure Research, Medical University of Warsaw, 5 Chałubińskiego Str., 02 004, Warsaw, Poland

    Izabela Młynarczuk-Biały, Agnieszka Czajkowska & Alicja Sztokfisz

  3. Crystallochemistry Laboratory, Faculty of Chemistry, University of Warsaw, 1 Pasteura Str., 02 093, Warsaw, Poland

    Łukasz Dobrzycki

  4. Department of Antibiotics and Microbiology, National Medicines Institute, 30/34 Chełmska Str., 00 725, Warsaw, Poland

    Hanna Kruszewska

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  1. Kinga Ostrowska
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Correspondence to Kinga Ostrowska.

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Ostrowska, K., Grzeszczuk, D., Maciejewska, D. et al. Synthesis and biological screening of a new series of 5-[4-(4-aryl-1-piperazinyl)butoxy]coumarins. Monatsh Chem 147, 1615–1627 (2016). https://doi.org/10.1007/s00706-016-1725-7

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  • DOI: https://doi.org/10.1007/s00706-016-1725-7

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