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New γ-Halo-δ-lactones and δ-Hydroxy-γ-lactones with Strong Cytotoxic Activity

1
Institute of Chemistry, Jan Kochanowski University, Świętokrzyska 15 G, 25-406 Kielce, Poland
2
Institute of Biology, Jan Kochanowski University, Świętokrzyska 15 G, 25-406 Kielce, Poland
3
Department of Chemistry, University of Wroclaw, F. Joliot-Curie 14, 50-383 Wrocław, Poland
4
Department of Chemistry, University of Warsaw, Żwirki i Wigury 101, 02-089 Warszawa, Poland
5
Department of Immunology and Infectious Biology, University of Lodz, Banacha 12/16, 90-237 Łódź, Poland
*
Author to whom correspondence should be addressed.
Molecules 2019, 24(10), 1875; https://doi.org/10.3390/molecules24101875
Received: 24 April 2019 / Revised: 7 May 2019 / Accepted: 9 May 2019 / Published: 15 May 2019
(This article belongs to the Special Issue New Studies on the Synthesis of Biologically Active Products)
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Abstract

This paper presents the synthesis of γ -halo- δ -lactones, δ -iodo- γ -lactones and δ -hydroxy- γ -lactones from readily available organic substrates such as trans-crotonaldehyde and aryl bromides. Crystal structure analysis was carried out for lactones that were obtained in crystalline form. All halo- δ -lactones and δ -hydroxy- γ -lactones were highly cytotoxic against gastric cancer AGS cells with I C 50 values in the range of 0.0006–0.0044 mM. Some lactones showed high bactericidal activity against E. coli ATCC 8739 and S. aureus ATCC 65389, which reduced the number of CFU/mL by 70–83% and 87% respectively. View Full-Text
Keywords: halolactones; translactonization; hydroxylactones; anti-cancer properties; bactericidal properties halolactones; translactonization; hydroxylactones; anti-cancer properties; bactericidal properties
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).
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Kamizela, A.; Gawdzik, B.; Urbaniak, M.; Lechowicz, Ł.; Białońska, A.; Kutniewska, S.E.; Gonciarz, W.; Chmiela, M. New γ-Halo-δ-lactones and δ-Hydroxy-γ-lactones with Strong Cytotoxic Activity. Molecules 2019, 24, 1875.

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