Febrifugine

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]

Quick facts Names, Identifiers ...

Febrifugine

Names
IUPAC name 3-{3-[(2R,3S)-3-Hydroxypiperidin-2-yl]-2-oxopropyl}quinazolin-4(3H)-one
Identifiers
CAS Number	24159-07-7 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL479432 Y
ChemSpider	8027405 N
ECHA InfoCard	100.208.679
PubChem CID	9851692
UNII	89UWD0FH2I Y
CompTox Dashboard (EPA)	DTXSID30946987
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 N Key: FWVHWDSCPKXMDB-CABCVRRESA-N N
SMILES C1C[C@@H]([C@H](NC1)CC(=O)CN2C=NC3=CC=CC=C3C2=O)O
Properties
Chemical formula	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). N verify (what is YN ?) Infobox references

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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.^[3]