1169933-45-2Relevant academic research and scientific papers
Studies on quinones. Part 47. Synthesis of novel phenylaminophenanthridinequinones as potential antitumor agents
Valderrama, Jaime A.,Ibacache, Andrea,Rodriguez, Jaime A.,Theoduloz, Cristina,Benites, Julio
, p. 3398 - 3409 (2011/08/03)
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 MTT 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 cycloaliphatic ring of the phenylamino-3,4-tetrahydrophenanthridine-1,7,10(2H)- trione pharmacophore play key roles in the antitumor activity.
Regiochemical control in the amination reaction of phenanthridine-7,10-quinones
Valderrama, Jaime A.,Ibacache, J. Andrea
scheme or table, p. 4361 - 4363 (2009/10/26)
The reaction of substituted phenanthridine-7,10-quinones with amines to construct novel aminophenanthridinequinone derivatives as antitumor agents is described. The regiochemistry of the amination reaction is discussed in terms of inductive and steric eff
