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

被引：45
|
作者：
Seo, Young Hwa [1 ,2 ]
Kim, Jin-Kyung [3 ]
Jun, Jong-Gab [1 ,2 ]
机构：
[1] Hallym Univ, Dept Chem, Chunchon 200702, South Korea
[2] Hallym Univ, Inst Appl Chem, Chunchon 200702, South Korea
[3] Catholic Univ Daegu, Coll Nat Sci, Dept Biomed Sci, Gyeungsan Si 700702, South Korea
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2014年 / 24卷 / 24期
基金：
新加坡国家研究基金会;
关键词：
3,4,5-Trimethoxycinnamic acid; Piperlongumine; Nitric oxide; Anti-inflammatory; CANCER-CELLS; PIPER-TUBERCULATUM; PIPLARTINE; ANALOGS; INHIBITION; ANTICANCER; LONGUM; AMIDES;
D O I：
10.1016/j.bmcl.2014.10.054
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
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 mu M) but showed cytotoxicity whereas compound 3 (IC50 = 6 mu M) which possess alpha,beta-unsaturated gamma-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 alpha,beta-unsaturation is fruitful to show potent anti-inflammatory activity. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5727 / 5730
页数：4
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