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

SUBMITTER: Kamizela A 

PROVIDER: S-EPMC6055027 | biostudies-literature | 2018 Jul

REPOSITORIES: biostudies-literature