Abstract
Three polyhydroxy-2-phenylnaphthalenes (1-3) and the oxy analogue of tetrahydroxypavinan (4) were prepared and evaluated for their antioxidant properties (inhibition of diphenylpycrylhydrazyl radical (DPPH), reduction of iron (III) ion) and inhibition of 5-lipoxygenase (5-LO) activity. Their three-dimensional structures were established on the basis of spectroscopic data and semiempirical calculations. Compounds 1 and 2 were found as potent 5-LO inhibitors as nordihydroguaiaretic acid (NDGA), whereas 4 is 2.5 times less potent than NDGA. The reliability of the 3-D structures with the 5-LO inhibition properties is discussed. Their antioxidant properties show that tested compounds are expected to act as redox inhibitors.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Antioxidants / chemical synthesis
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Antioxidants / pharmacology
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Arachidonate 5-Lipoxygenase / drug effects*
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Arachidonate 5-Lipoxygenase / metabolism
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Bepridil / analogs & derivatives*
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Bepridil / metabolism
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Biphenyl Compounds
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Catechols
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Indicators and Reagents
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Iron / metabolism
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Kinetics
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Lipoxygenase Inhibitors / chemical synthesis*
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Lipoxygenase Inhibitors / pharmacology
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Molecular Structure
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Oxidation-Reduction
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Picrates*
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Rats
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Structure-Activity Relationship
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Tumor Cells, Cultured
Substances
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Antioxidants
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Biphenyl Compounds
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Catechols
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Indicators and Reagents
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Lipoxygenase Inhibitors
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Picrates
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Bepridil
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1,1-diphenyl-2-picrylhydrazyl
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Iron
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Arachidonate 5-Lipoxygenase