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Please use this identifier to cite or link to this item: http://dspace.utalca.cl/handle/1950/4127

Title: Studies on quinones. Part 40: Synthesis and cytotoxicity evaluation of anthraquinone epoxides and isomerization products
Authors: Valderrama, J.A.
Espinoza, O.
Gonzalez, M.F.
Tapia, R.A
Rodriguez, J.
Theoduloz, C.
Schmeda-Hirschmann, G.
Keywords: Diels–Alder adducts; Aerobic epoxidation; Rearrangement; Angular quinones; Cytotoxicity
Issue Date: 2006
Publisher: Elsevier Ltd.
Citation: Tetrahedron 62 (11): 2631-2638
Abstract: Aerobic oxidation of 1,4,4a,10a-tetrahydro-1,4-alkano-5,10-anthraquinones and thiophene-analogues in dichloromethane–DBU yielded the corresponding dihydroalkanoquinones which, depending on their structures, react with in situ generated hydroperoxide anion to give quinone epoxides and/or hydroperoxides. The calcium hydroxide-induced rearrangement of quinone epoxides yielded furan-containing angular quinones. The cytotoxic activities of quinone epoxides and their isomerization products were evaluated in vitro against normal human lung fibroblasts (MRC-5) and human cancer gastric epithelial cells (AGS). Aerobic oxidation of Diels–Alder adducts of naphthoquinones and thiophene-analogues in dichloromethane–DBU provides access to quinone epoxides.
Description: Rodriguez,J.;Theoduloz, C. and Schmeda-Hirschmann, G. Laboratorio de Cultivo Celular, Facultad de Ciencias de la Salud, and Instituto de Química de Recursos Naturales, Universidad de Talca, Casilla 747, Talca, Chile
URI: http://dspace.utalca.cl/handle/1950/4127
ISSN: 0040-4020
Appears in Collections:Artículos en publicaciones ISI - Universidad de Talca

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