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

Soo Sung Kang, Muriel Cuendet, Denise C. Endringer, Vicki L. Croy, John M. Pezzuto, Mark A. Lipton

Research output: Contribution to journalArticlepeer-review

78 Scopus citations

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-κB. 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.

Original languageEnglish
Pages (from-to)1044-1054
Number of pages11
JournalBioorganic and Medicinal Chemistry
Volume17
Issue number3
DOIs
StatePublished - 1 Feb 2009

Keywords

  • Cyclooxygenase
  • Inhibition
  • NF-κB
  • Parallel synthesis
  • Resveratrol analogues

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