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1,4-Dihydronaphthoquinones as water-soluble inhibitors of 5-lipoxygenase

1990; Elsevier BV; Volume: 39; Issue: 4 Linguagem: Inglês

10.1016/0952-3278(90)90003-4

1532-2823

Robert G. Schaub, Ayako Yamashita, M K Bach, Gordon J. White, A. Toy, Nabil B. Ghazal, Carol A. Simmons, Michael D. Burdick, John R. Brashler, Marilyn S. Holm,

Morinda citrifolia extract uses

The acetate derivatives of 1,4-dihydronaphthoquinones showed significant inhibition of 5-lipoxygenase. Among them, 1-acetyl-2-n-butyl-4-methoxy-naphthalene and 1-acetyl-2, 3-diethyl-4-methoxynaphthalene were found to be the best inhibitors. A series of HCl salts of the amino acid esters and other derivatives of the two parent molecules, 1-hydroxy-2-n-butyl-4-methoxy-naphthalene and 1-hydroxy-2, 3-diethyl-4-methoxynaphthalene, were synthesized as water-soluble potential inhibitors of 5-lipoxygenase to improve the formulation characteristics of this class of compounds. The derivatives were evaluated for leukotriene (LT) and LTB4 inhibitory activity. The HCl salts of the L-valine esters from the two parent molecules exhibited the best potency for inhibition of (IC50 0.11-0.90 μM) in ionophore A23187-stimulated rat mononuclear cells and of LTB4 in A23187-stimulated rat blood (55.5–79.2% inhibition) following a single oral dose of 50 mg/kg.