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Please use this identifier to cite or link to this item: http://dspace.utalca.cl/handle/1950/8804

Title: Studies on quinones. Part 47. Synthesis of novel phenylaminophenanthridinequinones as potential antitumor agents
Authors: Valderrama, J.A.
Ibacache, A.
Rodriguez, J.A.
Theoduloz, C.
Benites, J.
Keywords: Cytotoxicity
Aminophenanthridinequinones
Regioselectivity
Half-wave potentials
Issue Date: Aug-2011
Publisher: ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES
Citation: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY Volume: 46 Issue: 8 Pages: 3398-3409 DOI: 10.1016/j.ejmech.2011.05.003
Abstract: In our search for potential anticancer agents, a series of 8- and 9-phenylamino-3,4-tetrahydro-phenanthridine-1,7,10(2H)-triones with substituent variations at 6-, 8- and 9-positions were prepared using a highly efficient sequence involving: a) solar photoacylation reactions of benzoquinone with arylaldehydes, b) one-pot procedure for the synthesis of 3,4-dihydrophenanthridine-1,7,10(2H)-trione intermediates from acylhydroquinones and c) highly regiocontrolled acid-induced amination reaction of phenanthridinequinones with phenylamines. The members of this series were in vitro evaluated using the KIT colorimetric method against one normal cell line and three human cancer cell lines. The SAR analysis indicates that the location of nitrogen substituents on the quinone nucleus, the presence of methyl, phenyl, furyl and thienyl groups at the 6-position and the aromatization of the angular cyclo-aliphatic ring of the phenylamino-3,4-tetrahydrophenanthridine-1,7,10(2H)-trione pharmacophore play key roles in the antitumor activity. (C) 2011 Elsevier Masson SAS. All rights reserved.
Description: Rodriguez, JA (Rodriguez, Jaime A.). Theoduloz, C (Theoduloz, Cristina);Univ Talca, Fac Ciencias Salud, Talca, Chile.
URI: http://dspace.utalca.cl/handle/1950/8804
ISSN: 0223-5234
Appears in Collections:Artículos en publicaciones ISI - Universidad de Talca

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