O-alkylcarboxylate oxime and N-hydroxyurea analogs of substituted indole leukotriene biosynthesis inhibitors

Reference FLAP inhibitors 1 and 2 were converted into the corresponding O-acetic acid oxime congeners 8 and 11a, respectively, resulting in potent, orally active, leukotriene biosynthesis inhibitors. An attempt to create a dual FLAP and direct 5-LO inhibitor by replacing the carboxylate group in 1 with the N-hydroxyurea pharmacophore did not provide superior inhibitors.