Nitrogen analogs of 1,4-benzoquinones. Activities against the ascitic sarcoma 180 of mice

Abstract

Compounds having the basic structure N-(R)-substituted ring-substituted 4-iminocyclohexadienone were synthesized and tested as antitumor agents against the ascitic sarcoma 180 tumor in Swiss mice. Among these compounds, the dimethylindoanilines [R = 4-(CH3)2NC6H4] are most stable in water at pH 7.0 and at 25.degree. C, the oximes (R = OH) are less stable, and the N-halo compounds (R = Br and Cl) are least stable. The N-halo derivatives have the highest redox potentials under conditions used, the greatest effect against ascitic sarcoma 180 in Swiss mice and the greatest acute toxicity when injected i.p. in Swiss mice. The redox potential, a molecular parameter, is the best single variable for discriminating between the groups based on antitumor activities.