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

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...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2014-12, Vol.24 (24), p.5727-5730
Main Authors: Seo, Young Hwa, Kim, Jin-Kyung, Jun, Jong-Gab
Format: Article
Language:English
Subjects:
Animals
Anti-Inflammatory Agents - chemical synthesis
Anti-Inflammatory Agents - pharmacology
Cell Proliferation - drug effects
Cells, Cultured
Dioxolanes - chemistry
Inflammation - chemically induced
Inflammation - metabolism
Inflammation - prevention & control
Lipopolysaccharides - pharmacology
Macrophages - cytology
Macrophages - drug effects
Mice
Molecular Structure
Nitric Oxide - metabolism
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Summary: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.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2014.10.054