Febrifugine

Febrifugine
Names

IUPAC name 3-{3-[(2R,3S)-3-Hydroxypiperidin-2-yl]-2-oxopropyl}quinazolin-4(3H)-one
Identifiers
CAS Registry Number	24159-07-7^Y
ChEMBL	ChEMBL479432^Y
ChemSpider	8027405^N
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
Jmol-3D images	Image
PubChem	9851692
SMILES C1C[C@@H]([C@H](NC1)CC(=O)CN2C=NC3=CC=CC=C3C2=O)O
Properties
Molecular formula	C₁₆H₁₉N₃O₃
Molar mass	301.34 g·mol⁻¹
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N verify (what is: Y/N?)
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.

References

↑ 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.
↑ 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.