Piperlongumine
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| Names | |
|---|---|
| IUPAC name
1-[(2E)-3-(3,4,5-Trimethoxyphenyl)prop-2-enoyl]-5,6-dihydropyridin-2(1H)-one | |
| Other names
Piplartine | |
| Identifiers | |
20069-09-4  | |
| 3D model (Jmol) | Interactive image |
| ChEMBL | ChEMBL465843  |
| ChemSpider | 553441 |
| PubChem | 637858 |
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| |
| Properties | |
| C17H19NO5 | |
| Molar mass | 317.34 g·mol−1 |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| verify (what is ?) | |
| Infobox references | |
Piperlongumine (PL) is a natural product constituent of the fruit of the Long pepper (Piper longum),[1] a pepper plant found in southern India and southeast Asia.
Piperlongumine may have anti-cancer properties. In in vitro experiments, it selectively kills some types cancer cells over normal cells.[1] One study in a xenograft mouse model of cancer showed that piperlongumine inhibits the growth of malignant breast tumors and their associated metastases.[1][2]
Some piperlongumine derivatives were potent anti-inflammatory agents.[3] The synthesis typically involved Schotten-Baumann reaction between the acid chloride of 3,4,5-trimethoxycinnamic acid with the corresponding amines.
References
- 1 2 3 Raj, Lakshmi; Ide, Takao; Gurkar, Aditi U.; Foley, Michael; Schenone, Monica; Li, Xiaoyu; Tolliday, Nicola J.; Golub, Todd R.; et al. (2011). "Selective killing of cancer cells by a small molecule targeting the stress response to ROS". Nature. 475 (7355): 231–234. doi:10.1038/nature10167. PMC 3316487
. PMID 21753854. - ↑ "Novel Compound Selectively Kills Cancer Cells by Blocking Their Response to Oxidative Stress". ScienceDaily. July 2011.
- ↑ Seo, Young Hwa; Kim, Jin-Kyung; Jun, Jong-Gab (2014). "Synthesis and biological evaluation of piperlongumine derivatives as potent anti-inflammatory agents". Bioorganic & Medicinal Chemistry Letters. 24 (24): 5727–5730. doi:10.1016/j.bmcl.2014.10.054. ISSN 0960-894X.
External links
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