Synthesis and antibacterial and anticancer evaluations of alpha-methylene-gamma-butyrolactones.

Nine new alpha-methylene-gamma-butyrolactones were synthesized by the Reformatsky condensation of ethyl alpha-bromomethylacrylate with ketones, aldehydes, and an epoxide. A unique spirobutyrolactone class was prepared by reaction of the zinc alkyl derivative and N-methylisatins. The compounds were evaluated against L-1210 and P-388 leukemia and the 9KB carcinoma of the nasopharynx. They also were screened in a microbiocidal and an antifungal assay. The spiro methylene lactone of 5-iodo-N-methylisatin displayed activity in the P-388, 9KB, and antifungal screens.