词条 | Febrifugine |
释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 441877885 | ImageFile = Febrifugine.png | ImageSize = 200px | IUPACName = 3- | 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] References1. ^{{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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