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词条 Febrifugine
释义

  1. References

{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 441877885
| ImageFile = Febrifugine.png
| ImageSize = 200px
| IUPACName = 3-{3-[(2R,3S)-3-Hydroxypiperidin-2-yl]-2-oxopropyl}quinazolin-4(3H)-one
| OtherNames =
|Section1={{Chembox Identifiers
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI =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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = FWVHWDSCPKXMDB-CABCVRRESA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 24159-07-7
| PubChem = 9851692
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 8027405
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 479432
| SMILES = C1C[C@@H]([C@H](NC1)CC(=O)CN2C=NC3=CC=CC=C3C2=O)O
|Section2={{Chembox Properties
| C=16 | H=19 | N=3 | O=3
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}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]

References

1. ^{{cite journal | last1 = McLaughlin | first1 = N. P. | last2 = Evans | first2 = P. | title = Dihydroxylation of Vinyl Sulfones: Stereoselective Synthesis of (+)- and (−)-Febrifugine and Halofuginone | journal = The Journal of Organic Chemistry | year = 2010 | volume = 75 | issue = 2 | pages = 518–521 | pmid = 20000346 | doi = 10.1021/jo902396m }}
2. ^{{Cite journal | doi = 10.1021/jo990877k| pmid = 11674693| title = Catalytic Asymmetric Synthesis of Antimalarial Alkaloids Febrifugine and Isofebrifugine and Their Biological Activity| journal = The Journal of Organic Chemistry| volume = 64| issue = 18| pages = 6833| year = 1999| last1 = Kobayashi| first1 = Shū| last2 = Ueno| first2 = Masaharu| last3 = Suzuki| first3 = Ritsu| last4 = Ishitani| first4 = Haruro| last5 = Kim| first5 = Hye-Sook| last6 = Wataya| first6 = Yusuke}}
3. ^{{cite journal|last1=Keller|first1=Tracy L|last2=Zocco|first2=Davide|last3=Sundrud|first3=Mark S|last4=Hendrick|first4=Margaret|last5=Edenius|first5=Maja|last6=Yum|first6=Jinah|last7=Kim|first7=Yeon-Jin|last8=Lee|first8=Hak-Kyo|last9=Cortese|first9=Joseph F|last10=Wirth|first10=Dyann F|last11=Dignam|first11=John David|last12=Rao|first12=Anjana|last13=Yeo|first13=Chang-Yeol|last14=Mazitschek|first14=Ralph|last15=Whitman|first15=Malcolm|displayauthors=8|title=Halofuginone and other febrifugine derivatives inhibit prolyl-tRNA synthetase|journal=Nature Chemical Biology|year= 2012|volume=8|issue=3|pages=311–317|doi=10.1038/nchembio.790|pmid=22327401|pmc=3281520}}

2 : Quinazolinones|Piperidine alkaloids

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