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Acridone

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Acridone
Names
Preferred IUPAC name Acridin-9(10H)-one
Other names 9-Acridanone
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.578 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=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)Key: FZEYVTFCMJSGMP-UHFFFAOYSA-N
  • 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)Key: FZEYVTFCMJSGMP-UHFFFAOYAI
SMILES
  • C1=CC=C2C(=C1)C(=O)C3=CC=CC=C3N2
  • O=C1c3ccccc3Nc2ccccc12
Properties
Chemical formula C13H9NO
Molar mass 195.221 g·mol
Appearance yellow powder
Melting point 250 °C (482 °F; 523 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

See also

References

  1. Beak, Peter; Fry, Fred S.; Lee, Jaekeun; Steele, Frank (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. 98: 171–179. doi:10.1021/ja00417a027.
  2. C. F. H. Allen & G. H. W. McKee (1939). "Acridone". Organic Syntheses. 19: 6. doi:10.15227/orgsyn.019.0006.
  3. Austrian National Library, Reports of the monthly meetings of the Academy of Sciences
  4. HISASHI FUJIOKA; YUKIHIRO NISHIYAMA; HIROSHI FURUKAWA & NOBUO KUMADA (1989). "In Vitro and In Vivo Activities of Atalaphillinine and Related Acridone Alkaloids against Rodent Malaria". Antimicrobial Agents and Chemotherapy. 33 (1): 6–9. doi:10.1128/aac.33.1.6. PMC 171411. PMID 2653215.
  5. Kelly, Jane X.; Smilkstein, Martin J.; Brun, Reto; Wittlin, Sergio; Cooper, Roland A.; Lane, Kristin D.; Janowsky, Aaron; Johnson, Robert A.; Dodean, Rozalia A.; Winter, Rolf; Hinrichs, David J.; Riscoe, Michael K. (2009). "Discovery of dual function acridones as a new antimalarial chemotype". Nature. 459 (7244): 270–273. Bibcode:2009Natur.459..270K. doi:10.1038/nature07937. PMC 8158239. PMID 19357645.
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