Aminoalkyl-Substituted 2-Hetarylimidazophenazines: Synthesis, DNA Binding and Cytotoxicity

A series of ethylamino- and propylamino-substituted 2-(pyridin-2-yl)imidazophenazines bearing various tertiary amine moieties, as well as a series of 2-hetarylimidazophenazines with N,N-diethylethan-1-amine moiety, were synthesized via the reaction of phenazine-2,3-diamine with heterocyclic aldehydes followed by alkylation with chloro-substituted alkylamines. In a study on HCT116, K562 and Kelly cells compounds containing N-methylindole, 2-chloroquinoline, and N-phenylpyrrole moieties exhibited the highest cytotoxicity. The values of binding constants with G-quadruplexes tel22, c-Myc for the leader compounds, determined by the method of fluorescence spectroscopy, were within the order of 105-106 M-1.