Synthesis, Characterization, Cytotoxicity, and Antibacterial Properties of trans ‐γ‐Halo‐δ‐lactones

Abstract: A new four‐step pathway for the synthesis of γ‐halo‐δ‐lactones is described from simple, commercially available substrates: aryl bromides and 3‐methyl crotonaldehyde. The halogenolactonization reaction of β,δ‐substituted, γ,δ‐unsaturated carboxylic acid 4 a–c is regio‐ and stereoselective and gives only the trans‐isomers of lactones 5 a–c, 6 a–c, and 7 a–c. The structures of all synthesized compounds were confirmed by using spectroscopic methods. For bromolactone, containing a naphthyl moiety in the structure, crystallographic analysis was also performed. The lactones were tested for their cytotoxic activity against L929 cell lines (mouse fibroblasts) and antibacterial activity against Escherichia coli strains ATCC 8739 and Staphylococcus aureus ATCC 65389. Compounds 5 a, 5 c, 7 a, and 7 b statistically significantly inhibited the metabolic activity of mouse fibroblasts L929. Compounds 5 b and 6 a were not cytotoxic towards L929 cells, but showed moderate bactericidal properties.

Object Details

• Location: Deutsche Nationalbibliothek Frankfurt am Main
• Extent: Online-Ressource
• Language: Englisch

References and Relationships

• Bibliographic citation: Synthesis, Characterization, Cytotoxicity, and Antibacterial Properties of trans ‐γ‐Halo‐δ‐lactones ; volume:7 ; number:7 ; year:2018 ; pages:543-550 ; extent:8 ; ChemistryOpen ; 7, Heft 7 (2018), 543-550 (gesamt 8)

Contributors, Places and Time

• Creator: Kamizela, Angelika ; Gawdzik, Barbara ; Urbaniak, Mariusz ; Lechowicz, Łukasz ; Białońska, Agata ; Gonciarz, Weronika ; Chmiela, Magdalena

Further information

• DOI: 10.1002/open.201800110
• URN: urn:nbn:de:101:1-2022083106444817669857
• Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
• Last update: 15.08.2025, 7:29 AM CEST