Design and synthesis of silicon-containing fatty acid amide derivatives as novel peroxisome proliferator-activated receptor (PPAR) agonists

Daisuke Kajita, Masaharu Nakamura, Yotaro Matsumoto, Minoru Ishikawa, Yuichi Hashimoto, Shinya Fujii

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

Abstract We recently reported that diphenylsilane structure can function as a cis-stilbene mimetic. Here, we investigate whether silyl functionality can also serve as a mimetic of aliphatic cis-olefin. We designed and synthesized various silyl derivatives of oleoylethanolamide (OEA: 8), an endogenous cis-olefin-containing PPARα agonist, and evaluated their PPARα/δ/γ agonistic activity. We found that diethylsilyl derivative 20 exhibited PPARα/δ agonistic activity, and we also obtained a PPARδ-selective agonist, 32. Our results suggest that incorporation of silyl functionality is a useful option for structural development of biologically active compounds.

Original languageEnglish
Article number22735
Pages (from-to)3350-3354
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume25
Issue number16
DOIs
Publication statusPublished - 2015 Jul 3

Keywords

  • PPAR
  • Peroxisome proliferator-activated receptor
  • Sila-substitution
  • Silicon
  • cis-Olefin mimetic

ASJC Scopus subject areas

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

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