Synthesis and Biological Activity of New 4-tert-Butylcyclohexanone Derivatives

Chem Biodivers. 2019 Feb;16(2):e1800411. doi: 10.1002/cbdv.201800411. Epub 2019 Jan 18.

Abstract

In the synthesis performed in this study, derivatives of 4-tert-butylcyclohexanone 1 were obtained using typical reactions of organic synthesis. The bioactivity of the selected compounds was evaluated. 1-(Bromomethyl)-8-tert-butyl-2-oxaspiro[4.5]decan-3-one (5) was characterized by attractant properties against larvae and a weak feeding deterrent activity against adults of Alphitobius diaperinus Panzer. This bromolactone was a moderate antifeedant towards Myzus persicae Sulzer. In addition, ethyl (4-tert-butylcyclohexylidene)acetate (2) and bromolactone 5 displayed antibacterial activity. The strongest bacteriostatic effect was observed against Gram-positive strains: Bacillus subtilis and Staphylococcus aureus. The bromolactone 5 also limited the growth of Escherichia coli strain.

Keywords: 4-tert-butylcyclohexanone; antibacterial activity; biological activity; lactones, bromolactones.

MeSH terms

  • Animals
  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / pharmacology*
  • Aphids / drug effects*
  • Bacillus subtilis / drug effects
  • Coleoptera / drug effects
  • Cyclohexanones / chemical synthesis
  • Cyclohexanones / pharmacology*
  • Escherichia coli
  • Insecticides / chemical synthesis
  • Insecticides / pharmacology*
  • Larva / drug effects
  • Staphylococcus aureus

Substances

  • Anti-Bacterial Agents
  • Cyclohexanones
  • Insecticides