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.
Takahashi
H
H
Institute of Molecular and Cellular Biosciences, The University of Tokyo, 1-1-1 Yayoi, Bunkvo-ku, Tokyo 113-0032, Japan.
Ishioka
T
T
Koiso
Y
Y
Sodeoka
M
M
Hashimoto
Y
Y
D000726:Androgen Antagonists / Q000138:chemical synthesis* / Q000494:pharmacology* / Q000633:toxicity; D001391:Azo Compounds / Q000138:chemical synthesis* / Q000494:pharmacology* / Q000633:toxicity; D001555:Benzene Derivatives / Q000138:chemical synthesis* / Q000494:pharmacology* / Q000633:toxicity; D018922:HL-60 Cells; D006801:Humans; D007928:Lethal Dose 50; D009682:Magnetic Resonance Spectroscopy; D011944:Receptors, Androgen / Q000378:metabolism; D018160:Receptors, Cytoplasmic and Nuclear / Q000187:drug effects / Q000378:metabolism; D013329:Structure-Activity Relationship
D000726:Androgen Antagonists; D001391:Azo Compounds; D001555:Benzene Derivatives; D011944:Receptors, Androgen; D018160:Receptors, Cytoplasmic and Nuclear