Peroxisome proliferator-activated receptor agonists with phenethylphenylphthalimide skeleton derived from thalidomide-related liver X receptor antagonists: Relationship between absolute configuration and subtype selectivity

Kazunori Motoshima, Minoru Ishikawa, Yuichi Hashimoto, Kazuyuki Sugita

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

Introduction of an alkylcarboxylic acid unit, which is a partial structure of endogenous peroxisome proliferator-activated receptor (PPAR) ligands, into a phenethylphenylphthalimide skeleton, which possesses liver X receptor (LXR) antagonistic activity, afforded novel PPAR ligands. The results of structure-activity relationship analysis and docking studies led us to the potent PPAR agonists 13c-e. The absolute configuration of 13c-e affects the PPAR subtype selectivity.

Original languageEnglish
Pages (from-to)3156-3172
Number of pages17
JournalBioorganic and Medicinal Chemistry
Volume19
Issue number10
DOIs
Publication statusPublished - 2011 May 15
Externally publishedYes

Keywords

  • Molecular design
  • Nuclear receptor
  • PPAR agonist
  • Subtype selectivity

ASJC Scopus subject areas

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

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