Anti-androgenic activity of substituted azo- and azoxy-benzene derivatives.

Substituted phenylazo and phenylazoxy compounds were systematically prepared and their anti-androgenic activity was measured in terms of (1) the growth-inhibiting effect on an androgen-dependent cell line, SC-3, and (2) the binding affinity to nuclear androgen receptor. Generally, azo/azoxy compounds showed cell toxicity, and the growth-inhibiting effects on SC-3 cells correlated with the toxicity. However, some compounds, including 4,4'-dinitroazobenzene (25), 4,4'-dimethoxyazobenzene (33), and 2,2'-dichloroazoxybenzene (47), possessed potent anti-androgenic activity without apparent cell toxicity.