Synthesis and biological evaluation of a library of resveratrol analogues as inhibitors of COX-1, COX-2 and NF-kappaB.

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Kang SS, Cuendet M, Endringer DC, Croy VL, Pezzuto JM, Lipton MA

Synthesis and biological evaluation of a library of resveratrol analogues as inhibitors of COX-1, COX-2 and NF-kappaB.

Bioorg Med Chem. 2009 Feb 1;17(3):1044-54. doi: 10.1016/j.bmc.2008.04.031. Epub 2008 May 16.

PubMed ID

18487053 [ View in PubMed

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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.

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Binding Properties

Drug	Target	Property	Measurement	pH	Temperature (°C)
Resveratrol	Prostaglandin G/H synthase 2	IC 50 (nM)	990	N/A	N/A	Details