Synthetic procedures have been developed which lead to the 2-aza congeners 3 and several related N-oxides 4. The analogues 3 exhibited a wide range of in vitro cytotoxicity against L1210 leukemia, the human colon adenocarcinoma cell line LoVo, and the doxorubicin resistant LoVo/DX cell line. Selected analogues of 3 showed significant P388 antileukemic activity in mice with 3c exhibiting high activity. This activity was also retained in the related N-oxide 4a. These heterocyclic bioisosteric models are representative of the first anthracene-9,10-diones which display antileukemic activity comparable to mitoxantrone.

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method. On removal of the ether a light yellow crystalline residue, a melting point of 141 °C was obtained. Recrystallization from methanol gave needles: mp 146-147 °C;llb yield 0.4 g (77.5%); IR (KBr) 1700 cm'1 (C=0, ester); NMR (CDC13) 3.9 (s, 6 H), 7.66 (s, 2 H).