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Febrifugine

From Wikipedia, the free encyclopedia
Febrifugine
Names
IUPAC name
3-{3-[(2R,3S)-3-Hydroxypiperidin-2-yl]-2-oxopropyl}quinazolin-4(3H)-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard100.208.679Edit this at Wikidata
UNII
  • 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 ☒N
    Key: FWVHWDSCPKXMDB-CABCVRRESA-N ☒N
  • C1C[C@@H]([C@H](NC1)CC(=O)CN2C=NC3=CC=CC=C3C2=O)O
Properties
C16H19N3O3
Molar mass301.346 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound

Febrifugine is aquinazolinonealkaloid first isolated from the Chinese herbDichroa febrifuga, but also found in the garden plantHydrangea.[1] Laboratory synthesis of febrifugine determined that the originally reported stereochemistry was incorrect.[2]

Febrifugine hasantimalarial properties and the synthetichalogenatedderivativehalofuginone is used in veterinary medicine as acoccidiostat. Other synthetic febrifugine derivatives have been used against malaria, cancer, fibrosis, and inflammatory disease.[3]

References

[edit]
  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):6833–6841.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.
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