Open AccessSynthesis, Characterization, Cytotoxicity, and Antibacterial Properties of trans ‐γ‐Halo‐δ‐lactones
Author(s) -
Kamizela Angelika,
Gawdzik Barbara,
Urbaniak Mariusz,
Lechowicz Łukasz,
Białońska Agata,
Gonciarz Weronika,
Chmiela Magdalena
Publication year - 2018
Publication title -
chemistryopen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.644
H-Index - 29
ISSN - 2191-1363
DOI - 10.1002/open.201800110
Subject(s) - crotonaldehyde , chemistry , moiety , stereoselectivity , escherichia coli , cytotoxicity , stereochemistry , antibacterial activity , cytotoxic t cell , aryl , staphylococcus aureus , bacteria , organic chemistry , biochemistry , in vitro , biology , catalysis , genetics , alkyl , gene
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.