Bradley University, Mund-Lagowski Department of Chemistry and Biochemistry, Peoria, IL 61625
Through an unexpected condensation reaction between β-keto-esters and benzaldehydes, highly substituted 5-aryl-3-oxo-δ-lactones can be synthesized in a single-pot reaction. It has also been found that the resulting lactones exhibit antibiotic activity against both Gram-positive and Gram-negative bacteria. As a preliminary assessment of activity, antibiotic susceptibility tests (minimum inhibitory concentrations (MIC)) against Bacillus subtilis were performed on these novel compounds. The effect of varying substituents on both the lactone and benzene rings was investigated. From this work it was discovered that hydrophobic substituents, in this case a spirobutane ring attached to the lactone, enhance the activity of the compounds as do electron withdrawing hydrophobic substituents on the benzene ring. Results from both our synthetic efforts and the antibiotic susceptibility testing of these compounds will be presented.
[Abstract (DOCX)]