2. Academic Validation
  3. Synthesis and biological evaluation of piperlongumine derivatives as potent anti-inflammatory agents

Synthesis and biological evaluation of piperlongumine derivatives as potent anti-inflammatory agents

  • Bioorg Med Chem Lett. 2014 Dec 15;24(24):5727-5730. doi: 10.1016/j.bmcl.2014.10.054.
Young Hwa Seo 1,  Jin-Kyung Kim 2,  Jong-Gab Jun 3
Affiliations

Affiliations

  • 1 Department of Chemistry and Institute of Applied Chemistry, Hallym University, Chuncheon 200-702, Republic of Korea.
  • 2 Department of Biomedical Science, College of Natural Science, Catholic University of Daegu, Gyeungsan-Si 700-702, Republic of Korea.
  • 3 Department of Chemistry and Institute of Applied Chemistry, Hallym University, Chuncheon 200-702, Republic of Korea. Electronic address: [email protected].
PMID: 25453809 DOI: 10.1016/j.bmcl.2014.10.054
Abstract

Piperlongumine (PL) and its derivatives were synthesized by the direct reaction between acid chloride of 3,4,5-trimethoxycinnamic acid and various amides/lactams. Later their anti-inflammatory effects were evaluated in lipopolysaccharide (LPS)-induced RAW-264.7 macrophages. Of the piperlogs prepared in this study, the maximum (91%) inhibitory activity was observed with PL (IC50=3 μM) but showed cytotoxicity whereas compound 3 (IC50=6 μM) which possess α,β-unsaturated γ-butyrolactam moiety offered good level (65%) of activity with no cytotoxicity. This study revealed that amide/lactam moiety connected to cinnamoyl group with minimum 3 carbon chain length and α,β-unsaturation is fruitful to show potent anti-inflammatory activity.

Keywords

3,4,5-Trimethoxycinnamic acid; Anti-inflammatory; Nitric oxide; Piperlongumine.

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