2-Anthracenonyl acetic acids as 5-lipoxygenase inhibitors.
The synthesis of 2-substituted anthracenonyl acetic acid (2-AA) derivatives is described. The key step is the Marschalk reaction of 1-hydroxy-8-methoxy-anthracenedione with glycolic acid. After protection of the resulting 2-anthracenonyl acetic acid derivative, the 2-monoalkylated derivatives are selectively obtained by direct alkylation. The methodology proves quite general and allows for the introduction of various substituents onto the 2-position of the carboxylic side chain. Reduction of the anthracenediones proceeds with concomitant protecting group removal and provides final 2-AA products in good yields. The results of initial biological studies demonstrate enhanced 5-lipoxygenase inhibition compared to anthralin.
Prinz
H
H
Institut für Pharmazie, Pharmazeutische Chemie I, Universität Regenburg, Germany.
Müller
K
K
D000085:Acetates / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D000873:Anthracenes / Q000138:chemical synthesis* / Q000494:pharmacology; D002417:Cattle; D066298:In Vitro Techniques; D016859:Lipoxygenase Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D009504:Neutrophils / Q000187:drug effects / Q000201:enzymology; D010084:Oxidation-Reduction
D000085:Acetates; D000873:Anthracenes; D016859:Lipoxygenase Inhibitors