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Updated: May 11, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Lactones 43. New biologically active lactones: β-cyclocitral derivatives
Marcelina Mazur1, Witold Gładkowski, Magdalena Podkowik
1Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375, Wrocław, Poland.
Background:
In our previous studies bicyclic γ-lactones with cyclohexane ring exhibited high antifeedant activity against storage pests. The activity was correlated with the type and number of substituents in the cyclohexane ring. One of the most potent group of antifeedant agents was δ-iodo-γ-lactones.
Results:
We present the synthesis of new bicyclic γ-lactones with the cyclohexane ring containing different halogen atoms. To determine the impact of halogen type on biological activity the lactone without halogen atom was also synthesized. The lactones were tested for their antifeedant activity toward the granary weevil beetle (Sitophilus granarius L.), the khapra beetle (Trogoderma granarium Everts) and the confused flour beetle (Tribolium confusum Du Val.). The results of the tests proved that the highest activity was observed for chlorolactone (7) towards larvae and adults of Tribolium confusum. Antibacterial activity of new lactones was also evaluated. Lactone without halogen atom (8) was active against Staphylococcus aureus and Listeria monocytogenes.
Conclusions:
Studies on the biological activity of synthesised lactones revealed high selectivity towards insect pests as well as bacterial strains. Only the halolactones exhibited significant antifeedant activity. In contrast, antibacterial activity was shown only by the lactone (8) without halogen.
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