Febrifugine

Febrifugine

Names
IUPAC name 3-{3-[(2R,3S)-3-Hydroxypiperidin-2-yl]-2-oxopropyl}quinazolin-4(3H)-one
Identifiers
CAS Number	24159-07-7
ChEMBL	ChEMBL479432
ChemSpider	8027405
Jmol interactive 3D	Image
PubChem	9851692
InChI InChI=1S/C16H19N3O3/c20-11(8-14-15(21)6-3-7-17-14)9-19-10-18-13-5-2-1-4-12(13)16(19)22/h1-2,4-5,10,14-15,17,21H,3,6-9H2/t14-,15+/m1/s1 Key: FWVHWDSCPKXMDB-CABCVRRESA-N
SMILES C1C[C@@H]([C@H](NC1)CC(=O)CN2C=NC3=CC=CC=C3C2=O)O
Properties
Chemical formula	C16H19N3O3
Molar mass	301.35 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Febrifugine is a quinazolinone alkaloid first isolated from the Chinese herb Dichroa febrifuga, but also found in the garden plant Hydrangea.^[1] Laboratory synthesis of febrifugine determined that the originally reported stereochemistry was incorrect.^[2]

Febrifugine has antimalarial properties and the halogenated derivative halofuginone is used in veterinary medicine as a coccidiostat. Halofuginone is specifically shown to be an effective drug in malaria, cancer, fibrosis and inflammatory disease.^[3]

References

1. McLaughlin, N. P.; Evans, P. (2010). "Dihydroxylation of Vinyl Sulfones: Stereoselective Synthesis of (+)- and (−)-Febrifugine and Halofuginone". The Journal of Organic Chemistry 75 (2): 518–521. doi:10.1021/jo902396m. PMID 20000346.
2. Kobayashi, Shū; Ueno, Masaharu; Suzuki, Ritsu; Ishitani, Haruro; Kim, Hye-Sook; Wataya, Yusuke (1999). "Catalytic Asymmetric Synthesis of Antimalarial Alkaloids Febrifugine and Isofebrifugine and Their Biological Activity". The Journal of Organic Chemistry 64 (18): 6833. doi:10.1021/jo990877k. PMID 11674693.
3. Keller, Tracy L; Zocco, Davide; Sundrud, Mark S; Hendrick, Margaret; Edenius, Maja; Yum, Jinah; Kim, Yeon-Jin; Lee, Hak-Kyo; et al. (2012). "Halofuginone and other febrifugine derivatives inhibit prolyl-tRNA synthetase". Nature Chemical Biology 8 (3): 311–317. doi:10.1038/nchembio.790. PMC 3281520. PMID 22327401.