Acridone

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title: "Acridone" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["aromatic-ketones", "acridines"] topic_path: "general/aromatic-ketones" source: "https://en.wikipedia.org/wiki/Acridone" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Verifiedfields = changed | verifiedrevid = 477241172 | ImageFile=acridone.svg | ImageSize=180px | PIN=Acridin-9(10H)-one | OtherNames= 9-Acridanone |Section1={{Chembox Identifiers | ChemSpiderID_Ref = | 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 = | ChEMBL = 436589 | StdInChI_Ref = | 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 = | StdInChIKey = FZEYVTFCMJSGMP-UHFFFAOYSA-N | CASNo_Ref = | CASNo=578-95-0 | UNII_Ref = | UNII = 6BK306GUQA | PubChem=2015 | ChEBI_Ref = | 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.

Acridone can be synthesized by heating fenamic acid.

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.

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.

References

References

  1. (1976). "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". Journal of the American Chemical Society.
  2. C. F. H. Allen. (1939). "Acridone". Organic Syntheses.
  3. [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]
  4. (1989). "In Vitro and In Vivo Activities of Atalaphillinine and Related Acridone Alkaloids against Rodent Malaria". Antimicrobial Agents and Chemotherapy.
  5. (2009). "Discovery of dual function acridones as a new antimalarial chemotype". Nature.

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