| Revision as of 14:35, 28 July 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (changes to verified fields - updated 'UNII_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report errors or [[user talk← Previous edit |
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{{Chembox |
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{{Chembox |
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| Verifiedfields = changed |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 400325991 |
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| verifiedrevid = 441877885 |
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| ImageFile = Febrifugine.png |
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| ImageFile = Febrifugine.png |
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| ImageSize = 200px |
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| ImageSize = 200px |
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| IUPACName = 3-{3--2-oxopropyl}quinazolin-4(3H)-one |
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| IUPACName = 3-<nowiki/>{3--2-oxopropyl}quinazolin-4(3''H'')-one |
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| OtherNames = |
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| OtherNames = |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| InChI = 1/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+/m0/s1 |
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| 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 |
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| InChIKey = FWVHWDSCPKXMDB-LSDHHAIUBU |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = FWVHWDSCPKXMDB-CABCVRRESA-N |
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| 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+/m0/s1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| CASNo_Ref = {{cascite|correct|??}} |
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| StdInChIKey = FWVHWDSCPKXMDB-LSDHHAIUSA-N |
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| CASNo = 24159-07-7 |
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| CASNo = 24159-07-7 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem = 63224 |
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| UNII = 89UWD0FH2I |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 56900 |
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| PubChem = 9851692 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 8027405 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 479432 |
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| ChEMBL = 479432 |
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| SMILES = O=C1c3ccccc3/N=C\N1CC(=O)C2NCCC2O |
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| SMILES = C1C((NC1)CC(=O)CN2C=NC3=CC=CC=C3C2=O)O |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=16|H=19|N=3|O=3 |
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| C=16 | H=19 | N=3 | O=3 |
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| Appearance = |
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| Appearance = |
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| Density = |
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| Density = |
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| MeltingPt = |
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| MeltingPt = |
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| BoilingPt = |
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| Solubility = |
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| Solubility = |
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}} |
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}} |
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| Section3 = {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards = |
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| MainHazards = |
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| FlashPt = |
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| FlashPt = |
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| Autoignition = |
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| AutoignitionPt = |
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}} |
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}} |
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}} |
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}} |
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'''Febrifugine''' is a ] alkaloid first isolated from Chinese herb '']'', but also found in the garden plant '']''.<ref>{{cite journal | last1 = McLaughlin | first1 = Noel P. | last2 = Evans | first2 = Paul | title = Dihydroxylation of Vinyl Sulfones: Stereoselective Synthesis of (+)- and (−)-Febrifugine and Halofuginone | journal = The Journal of Organic Chemistry | volume = 75 | issue = 2 | pages = 518 | year = 2010 | pmid = 20000346 | doi = 10.1021/jo902396m}}</ref> |
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'''Febrifugine''' is a ] ] first isolated from the Chinese herb '']'', but also found in the garden plant '']''.<ref>{{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 }}</ref> Laboratory synthesis of febrifugine determined that the originally reported stereochemistry was incorrect.<ref>{{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 = 6833–6841| 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}}</ref> |
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Febrifugine has ] properties and the synthetic ]ated ] ] is used in veterinary medicine as a ]. Other synthetic febrifugine derivatives have been used against malaria, cancer, fibrosis, and inflammatory disease.<ref>{{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|display-authors=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}}</ref> |
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Febrifugine has ] properties and the ]ated derivative ] is used in veterinary medicine as a ]. |
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==References== |
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== References == |
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