Efficient synthesis of substituted 7-methyl-2H,5H-pyrano[4,3-b]pyran-5-ones and evaluation of their in vitro antiproliferative/cytotoxic activities
- Publication Type
- Journal contribution (peer reviewed)
- Authors
- Leutbecher, H.; Williams, L. A. D.; Roesner, H.; Beifuss, U.
- Year of publication
- 2007
- Published in
- Bioorg. & Med. Chem. Lett.
- Band/Volume
- 17/4
- DOI
- 10.1016/j.bmcl.2006.11.045
- Page (from - to)
- 978-982
Substituted 7-methyl-2H,5H-pyrano[4,3-b]pyran-5-ones and related heterocycles were synthesized through an efficient domino Knoevenagel condensation/6π-electron electrocyclization. In vitro antiproliferative/cytotoxic activity evaluation was performed with human SH-SY5Y neuroblastoma cells and revealed IC50 values ranging from 6.7 to >200 μM. The compd. that was most cytotoxic to the neuroblastoma cells, i.e., 2-isobutyl-3-isopropyl-7-methyl-2H,5H-pyrano[4,3-b]pyran-5-one (I), also exhibited necrotic effects on the human IPC melanoma cells