Substituted 7-methyl-2H,5H-pyrano[4,3-b]pyran-5-ones and related heterocycles 3 were synthesized through an efficient domino Knoevenagel condensation/6pi-electron electrocyclization. In vitro antiproliferative/cytotoxic activity evaluation was performed with human SH-SY5Y neuroblastoma cells and revealed IC(50) values ranging from 6.7 to >200microM. The compound that was most cytotoxic to the neuroblastoma cells, that is, 2-isobutyl-3-isopropyl-7-methyl-2H,5H-pyrano[4,3-b]pyran-5-one (3a), also exhibited necrotic effects on the human IPC melanoma cells.
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The corresponding record at NLM can be accessed at https://www.ncbi.nlm.nih.gov/pubmed/17166717