Chromophore modification of the anthracenediones related to mitoxantrone (5) in an attempt to provide agents with diminished or no cardiotoxicity has resulted in a novel class of DNA binders, the anthrapyrazoles (9). Their synthesis was carried out by a two-stage condensation sequence starting from requisite 1, 4-or 1, 5-dichloro-9, 10-anthracenedione precursors. Reaction with a monoalkylhydrazine gave a chloroanthrapyrazole ...