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 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL479432 ;
ChemSpider	8027405 ;
ECHA InfoCard	100.208.679
PubChem CID	9851692;
UNII	89UWD0FH2I ;
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 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	301.346 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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 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.

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): 6833–6841. doi:10.1021/jo990877k. PMID 11674693.
↑ 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.

[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.