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Two new cationic DNA intercalators, 3-phenyl-1-(6-phenylpyridin-2-yl)-1 H -[1,2,4]triazolo[4,3- a ]pyridin-4-ium ( 1a ) +  and 1-phenyl-3-(6-phenylpyridin-2-yl)-3 H -[1,2,4]triazolo[4,3- a ]quinolin-10-ium ( 1b ) + , were synthesized from 2-chloropyridine and 2-chloroquinoline, respectively, in a four-step procedure. Generation of the hydrazine, followed by condensation with an aldehyde to give a hydrazone and subsequent Buchwald-Hartwig amination gave a mixture of  E - and  Z -configured  N , N -functionalized hydrazones. Finally, oxidative cyclisation gave rise to the formation of the cationic DNA intercalators, whose molecular structures were determined by single-crystal X-ray diffraction analysis of the hexafluorophosphate and tribromide salt of ( 1a ) +  and ( 1b ) + , respectively. The intercalative binding of ( 1a )PF 6  and ( 1b )PF 6  to ctDNA was confirmed by means of UV, CD and luminescence spectroscopy, determination of the DNA melting temperature and by rheology measurements.

1 H -[1,2,4]Triazolo[4,3- a ]pyridin-4-ium and 3 H -[1,2,4]triazolo[4,3- a ]quinolin-10-ium derivatives as new intercalating agents for DNA