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.
D015107:4-Butyrolactone / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000494:pharmacology*; D000818:Animals; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D000970:Antineoplastic Agents; D002478:Cells, Cultured; D004353:Drug Evaluation, Preclinical; D005663:Furans / Q000494:pharmacology*; D006801:Humans; D007939:Leukemia L1210 / Q000188:drug therapy; D007941:Leukemia P388 / Q000188:drug therapy; D051379:Mice; D009303:Nasopharyngeal Neoplasms / Q000188:drug therapy
D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D000970:Antineoplastic Agents; D005663:Furans; D015107:4-Butyrolactone