Efficient synthesis of (±)-parasitenone, a novel inhibitor of NF-κB

Tsuyoshi Saitoh, Eriko Suzuki, Arisa Takasugi, Rika Obata, Yuichi Ishikawa, Kazuo Umezawa, Shigeru Nishiyama

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

Dehydroxymethylepoxyquinomicin (DHMEQ, 1) is a novel nuclear factor-κB (NF-κB) inhibitor that inhibits DNA binding of NF-κB components including p65. To inspect its biological activity of 1, we synthesized parasitenone (3), possessing the common epoxycyclohexenone moiety of 1. Assessment of the inhibitory activity against NF-κB indicated that the epoxycyclohexenone moiety is the most essential element for the NF-κB inhibitory activity and the salicylic acid moiety may contribute the binding efficiency and specificity.

Original languageEnglish
Pages (from-to)5383-5386
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume19
Issue number18
DOIs
Publication statusPublished - 2009 Sep 15

Keywords

  • Anodic oxidation
  • DHMEQ
  • Epoxycyclohexenone
  • NF-κB inhibitor
  • Parasitenone

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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  • Cite this

    Saitoh, T., Suzuki, E., Takasugi, A., Obata, R., Ishikawa, Y., Umezawa, K., & Nishiyama, S. (2009). Efficient synthesis of (±)-parasitenone, a novel inhibitor of NF-κB. Bioorganic and Medicinal Chemistry Letters, 19(18), 5383-5386. https://doi.org/10.1016/j.bmcl.2009.07.120