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Febrifugine information


Febrifugine
Names
IUPAC name
3-{3-[(2R,3S)-3-Hydroxypiperidin-2-yl]-2-oxopropyl}quinazolin-4(3H)-one
Identifiers
CAS Number
  • 24159-07-7 checkY
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL479432 checkY
ChemSpider
  • 8027405 ☒N
ECHA InfoCard 100.208.679 Edit this at Wikidata
PubChem CID
  • 9851692
UNII
  • 89UWD0FH2I checkY
CompTox Dashboard (EPA)
  • DTXSID30946987 Edit this at Wikidata
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).
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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 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]

  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.

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Febrifugine

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Febrifugine is a quinazolinone alkaloid first isolated from the Chinese herb Dichroa febrifuga, but also found in the garden plant Hydrangea. Laboratory...

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Project 523

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against different species of Plasmodium. American scientists isolated febrifugine as its major active antimalarial compound. The project scientists confirmed...

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Dichroa febrifuga

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where it is considered one of the 50 fundamental herbs. The alkaloids febrifugine and isofebrifugine are believed to be responsible for its antimalarial...

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Halofuginone

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in veterinary medicine. It is a synthetic halogenated derivative of febrifugine, a natural quinazolinone alkaloid which can be found in the Chinese herb...

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Alkaloid

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4-Dihydro-4-quinazolone derivatives Anthranilic acid or phenylalanine or ornithine Febrifugine 1,4-Dihydro-4-quinazolone derivatives Glycorine, arborine, glycosminine...

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Quinazoline alkaloids

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1-b]quinazolines and indoloquinazolines. Vasicine Evodiamine Rutaecarpine Febrifugine Quinazoline alkaloids can be found mainly in plants, such as acanthaceae...

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C16H19N3O3

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C16H19N3O3 (molar mass: 301.34 g/mol, exact mass: 301.1426 u) may refer to: Febrifugine HIOC Prazitone (AGN-511) This set index page lists chemical structure...

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