Structural modification study of bis(substituted aminoalkylamino)anthraquinones. An evaluation of the relationship of the [2-[(2-hydroxyethyl)amino]ethyl]amino side chain with antineoplastic activity.

Several anthraquinones containing the [2-[(2-hydroxyethyl)amino]ethyl]amino, the [2-(dimethylamino)ethyl]amino, and the 2-(dimethylamino)ethoxy groups were prepared. Preparation of a lucanthone analogue, a 7-chloroquinoline derivative, and derivatives of naphthoquinones containing the [2-[(2-hydroxyethyl)amino]ethyl]amino side chain and related amino-substituted side chains was also conducted. It was found that the antineoplastic activity of anthraquinones containing the [2-[(2-hydroxyethyl)amino]ethyl]amino side chain is superior to those containing the tertiary amino side chain. However, the presence of the [2-[(2-hydroxyethyl)amino]ethyl]amino chain is an important, but not a sufficient, factor for good antineoplastic activity, as indicated by the lack of significant biological activity of other ring systems containing this side chain.