Zd. Huang et al., SYNTHESIS AND EVALUATION OF THE ANTITUMOR-ACTIVITY OF 4,5-DIAMINO-SUBSTITUTED 1,2-BENZOQUINONES, Journal of medicinal chemistry, 36(13), 1993, pp. 1797-1801
A series of 4,5-diamino-substituted-1,2-benzoquinones were prepared fr
om catechol and the corresponding secondary amines in high yield in a
single step using copper complex formation to stabilize the intermedia
te. The cytotoxicity of the products under various conditions was eval
uated using the EMT-6 mammary carcinoma cell line, and antitumor activ
ity was tested in the L1210 murine leukemia. The 4,5-diaziridinyl-1,2-
benzoquinone was a more potent cytotoxic agent than diaziquone (AZQ) a
nd was very effective against the L1210 leukemia. The azetidine, pyrro
lidine, and diethylamine derivatives were not effective antitumor agen
ts.