{{chembox | Verifiedfields = changed | verifiedrevid = 477241172 | ImageFile=acridone.svg | ImageSize=180px | PIN=Acridin-9(10''H'')-one | OtherNames= 9-Acridanone |Section1={{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 10188539 | InChI = 1/C13H9NO/c15-13-9-5-1-3-7-11(9)14-12-8-4-2-6-10(12)13/h1-8H,(H,14,15) | InChIKey = FZEYVTFCMJSGMP-UHFFFAOYAI | SMILES1 = O=C1c3ccccc3Nc2ccccc12 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 436589 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C13H9NO/c15-13-9-5-1-3-7-11(9)14-12-8-4-2-6-10(12)13/h1-8H,(H,14,15) | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = FZEYVTFCMJSGMP-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo=578-95-0 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 6BK306GUQA | PubChem=2015 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 50756 | SMILES=C1=CC=C2C(=C1)C(=O)C3=CC=CC=C3N2 }} |Section2={{Chembox Properties | C=13 | H=9 | N=1 | O=1 | Appearance= yellow powder | Density= | MeltingPtC= 250 | BoilingPt= | Solubility= }} |Section3={{Chembox Hazards | MainHazards= | FlashPt= | AutoignitionPt = }} }} '''Acridone''' is an organic compound based on the acridine skeleton, with a carbonyl group at the ''9'' position.
==Synthesis and structure== The molecule is planar. Optical spectra reveal that the keto tautomer predominates in the gas-phase and in ethanol solution.<ref>{{cite journal |doi=10.1021/ja00417a027|title=Equilibration studies. Protomeric equilibria of 2- and 4-hydroxypyridines, 2- and 4-hydroxypyrimidines, 2- and 4-mercaptopyridines, and structurally related compounds in the gas phase|year=1976|last1=Beak|first1=Peter|last2=Fry|first2=Fred S.|last3=Lee|first3=Jaekeun|last4=Steele|first4=Frank|journal=Journal of the American Chemical Society|volume=98|pages=171–179}}</ref>
Acridone can be synthesized by heating fenamic acid.<ref>{{cite journal | title = Acridone | author = C. F. H. Allen | author2 = G. H. W. McKee | name-list-style = amp | volume= 19 | pages = 6 | doi = 10.15227/orgsyn.019.0006 | year = 1939|journal=Organic Syntheses}}</ref>
==History== One of the first who were able to prove the compound's existence was Karl Drechsler, Student of G. Goldschmiedt, at the k.u.k. Universität Wien (Vienna, Austria) in 1914.<ref>[http://anno.onb.ac.at/cgi-content/anno-plus?aid=mch&datum=1914&size=45&page=667 Austrian National Library, Reports of the monthly meetings of the Academy of Sciences]</ref>
==Derivatives== Acridone constitutes the scaffold of some synthetic compounds with diverse pharmacological activities. 3-Chloro-6-(2-diethylamino-ethoxy)-10-(2-diethylamino-ethyl)-acridone has shown promise as an antimalarial drug.<ref>{{cite journal | journal = Antimicrobial Agents and Chemotherapy | year = 1989 | pages = 6–9 |volume=33| issue=1 | title = In Vitro and In Vivo Activities of Atalaphillinine and Related Acridone Alkaloids against Rodent Malaria |author1=HISASHI FUJIOKA |author2=YUKIHIRO NISHIYAMA |author3=HIROSHI FURUKAWA |author4=NOBUO KUMADA |name-list-style=amp | pmid = 2653215 | pmc = 171411 | doi=10.1128/aac.33.1.6}}</ref><ref>{{cite journal |author1=Kelly, Jane X. |author2=Smilkstein, Martin J. |author3=Brun, Reto |author4=Wittlin, Sergio |author5=Cooper, Roland A. |author6=Lane, Kristin D. |author7=Janowsky, Aaron |author8=Johnson, Robert A. |author9=Dodean, Rozalia A. |author10=Winter, Rolf |author11=Hinrichs, David J. |author12=Riscoe, Michael K. | title = Discovery of dual function acridones as a new antimalarial chemotype | journal=Nature |year=2009 | volume=459 | issue=7244 |pages=270–273 | doi = 10.1038/nature07937 | pmid = 19357645|pmc=8158239 |bibcode=2009Natur.459..270K }}</ref>
==See also== * Quinacridone
==References== {{reflist}}
Category:Aromatic ketones Category:Acridines