Design and synthesis of new N-(fluorenyl-9-methoxycarbonyl) (Fmoc)-dipeptides as anti-inflammatory agents

Chiao Ting Yen, Tsong Long Hwang, Yang Chang Wu*, Pei Wen Hsieh

*Corresponding author for this work

Research output: Contribution to journalJournal Article peer-review

21 Scopus citations

Abstract

Twenty-four new dipeptide analogs (1-24) of aurantiamide acetate were designed, synthesized, and assayed for effects on superoxide anion generation and elastase release by human neutrophils in response to fMLP/CB. Among them, seven N-(fluorenyl-9-methoxycarbonyl) (Fmoc)-dipeptides (6, 9, 12, 14, 17, 18 and 20) showed potent inhibitory effects. Compounds 9 and 18 showed the most selective effects against human neutrophil elastase release, with IC50 values of 0.8 ± 0.1 and 1.7 ± 0.6 μM, respectively, and were 130-fold more potent than phenylmethylsulfonyl fluoride (PMSF), the positive control, in this anti-inflammatory assay. These two compounds could be developed as new lead anti-inflammatory agents.

Original languageEnglish
Pages (from-to)1933-1940
Number of pages8
JournalEuropean Journal of Medicinal Chemistry
Volume44
Issue number5
DOIs
StatePublished - 05 2009

Keywords

  • Anti-inflammatory agents
  • Aurantiamide derivatives
  • Fmoc-based dipeptides

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