Efficient synthesis of substituted 7-methyl-2H,5H-pyrano[4,3-b]pyran-5-ones and evaluation of their in vitro antiproliferative/cytotoxic activities

Publikations-Art

Zeitschriftenbeitrag (peer-reviewed)

Autoren

Leutbecher, H.; Williams, L. A. D.; Roesner, H.; Beifuss, U.

Erscheinungsjahr

2007

Veröffentlicht in

Bioorg. & Med. Chem. Lett.

Band/Volume

17/4

DOI

10.1016/j.bmcl.2006.11.045

Seite (von - bis)

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