Abstract
Resveratrol (4,3',5'-trihydroxystilbene) is a naturally occurring antioxidant that inhibits cyclooxygenase-1 (COX-1), cyclooxygenase-2 (COX-2) and the transcription factor NF-kappaB. A 78-membered library of resveratrol analogues in which the substituents on the two aryl rings and alkene were varied was synthesized using a solid-phase Wittig olefination reaction. The library contains inhibitors against all three proteins that were more potent than resveratrol itself. Preliminary structure-activity relationships were also obtained from these data that permitted the derivation of pharmacophore models for each of the three targets.
MeSH terms
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Antioxidants / chemical synthesis*
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Antioxidants / chemistry
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Antioxidants / pharmacology
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Cell Line
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Combinatorial Chemistry Techniques
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Cyclooxygenase 2 Inhibitors / chemical synthesis*
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Cyclooxygenase 2 Inhibitors / chemistry
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Cyclooxygenase 2 Inhibitors / pharmacology
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Cyclooxygenase Inhibitors / chemical synthesis*
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Cyclooxygenase Inhibitors / chemistry
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Cyclooxygenase Inhibitors / pharmacology
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Humans
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Inhibitory Concentration 50
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NF-kappa B / antagonists & inhibitors*
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NF-kappa B / metabolism
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Resveratrol
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Small Molecule Libraries
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Stilbenes / chemical synthesis
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Stilbenes / chemistry*
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Stilbenes / pharmacology
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Structure-Activity Relationship
Substances
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Antioxidants
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Cyclooxygenase 2 Inhibitors
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Cyclooxygenase Inhibitors
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NF-kappa B
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Small Molecule Libraries
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Stilbenes
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Resveratrol