Febrifugine

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

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 InfoCard 100.208.679
PubChem CID
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
SMILES
  • C1C[C@@H]([C@H](NC1)CC(=O)CN2C=NC3=CC=CC=C3C2=O)O
Properties
C16H19N3O3
Molar mass 301.346 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 has antimalarial properties and the synthetic halogenated derivative halofuginone is used in veterinary medicine as a coccidiostat. Other synthetic febrifugine derivatives have been used against malaria, cancer, fibrosis, and inflammatory disease.

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