Febrifugine Explained

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 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]

Notes and References

1. McLaughlin . N. P. . Evans . P. . Dihydroxylation of Vinyl Sulfones: Stereoselective Synthesis of (+)- and (−)-Febrifugine and Halofuginone . The Journal of Organic Chemistry . 2010 . 75 . 2 . 518–521 . 20000346 . 10.1021/jo902396m .
2. 10.1021/jo990877k. 11674693. Catalytic Asymmetric Synthesis of Antimalarial Alkaloids Febrifugine and Isofebrifugine and Their Biological Activity. The Journal of Organic Chemistry. 64. 18. 6833–6841. 1999. Kobayashi. Shū. Ueno. Masaharu. Suzuki. Ritsu. Ishitani. Haruro. Kim. Hye-Sook. Wataya. Yusuke.
3. Keller. Tracy L. Zocco. Davide. Sundrud. Mark S. Hendrick. Margaret. Edenius. Maja. Yum. Jinah. Kim. Yeon-Jin. Lee. Hak-Kyo. Cortese. Joseph F. Wirth. Dyann F. Dignam. John David. Rao. Anjana. Yeo. Chang-Yeol. Mazitschek. Ralph. Whitman. Malcolm. 8. Halofuginone and other febrifugine derivatives inhibit prolyl-tRNA synthetase. Nature Chemical Biology. 2012. 8. 3. 311–317. 10.1038/nchembio.790. 22327401. 3281520.