Anthraquinones The Antrone Chemotherapy Agents

The synthesis of the hrst of these agents starts with the dye intermediate leucoquinizarin (35-1), the reduction product of the dihydroxyanthraquinone, quinizarin. Condensation with A-(2-hydroxyethyl)ethylenediamine (35-2) leads to the corresponding bis imine (35-3). Air oxidation may be visualized as starting at the hydroquinone-like central ring bond reorganization will lead to ametrantrone (35-4) [35]. 

In much the same vein, condensation of the tetrahydroxy intermediate (36-1) with the same polyamine as above gives the analogous intermediate bis imine air oxidation of the intermediate then affords mitoxantrone (36-2) [36]. 

The symmetrical substimtion pattern in the foregoing starting anthraquinones greatly simplified the chemistry. The presence of but a single hydroxyl substituent 

Chilma-Blair, K. Castaner, J. Silvestre, J. S. Bayes, H. Drugs Future 2003, 28, 950. 

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