Synthesis of prenylated quinolinecarboxylic acid derivatives and their anti-obesity activities

Haruhisa Kikuchi, Toshiyuki Suzuki, Masato Ogura, Miwako K. Homma, Yoshimi Homma, Yoshiteru Oshima

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

Mitochondrial uncoupling is one of the therapeutic strategies used to control energy metabolism in various metabolic diseases and in obesity. Ppc-1 (1), a prenylated quinolinecarboxylic acid isolated from cellular slime molds, shows uncoupling activity in vitro and anti-obesity activity in vivo. In this study, we synthesized Ppc-1 (1) and its derivatives, and revealed the structure-activity relationship of uncoupling activities. The triprenylated compound 18 showed mitochondrial uncoupling activity that was more potent than that of Ppc-1 (1). Compound 18 also suppressed weight gain in mice without undesired effects such as lesions on tissues. These results indicate that compound 18 could be used as a seed compound for new anti-obesity drugs.

Original languageEnglish
Pages (from-to)66-72
Number of pages7
JournalBioorganic and Medicinal Chemistry
Volume23
Issue number1
DOIs
Publication statusPublished - 2015 Jan 1
Externally publishedYes

Keywords

  • Anti-obesity drugs
  • Metabolic diseases Quinolinecarboxylate
  • Mitochondrial uncoupling
  • Structure-activity relationship

ASJC Scopus subject areas

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

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