title: Efficient synthesis of substituted 7-methyl-2H,5H-pyrano[4,3-b]pyran-5-ones and evaluation of their in vitro antiproliferative/cytotoxic activities.
abstract: 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.
authors.affiliation: Bioorganische Chemie, Institut für Chemie der Universität Hohenheim, Garbenstr. 30, 70599 Stuttgart, Germany.
authors.forename: Heiko
authors.initials: H
authors.lastname: Leutbecher
authors.forename: Lawrence A D
authors.initials: LA
authors.lastname: Williams
authors.forename: Harald
authors.initials: H
authors.lastname: Rösner
authors.forename: Uwe
authors.initials: U
authors.lastname: Beifuss
mesh_terms: D000447:Aldehydes; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D002448:Cell Adhesion / Q000187:drug effects; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000494:pharmacology; D006801:Humans; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D011753:Pyrones / Q000138:chemical synthesis* / Q000494:pharmacology*; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet
chemical_list: D000447:Aldehydes; D000970:Antineoplastic Agents; D006571:Heterocyclic Compounds; D007202:Indicators and Reagents; D011753:Pyrones