Acridone Explained

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.^[1]

Acridone can be synthesized by heating fenamic acid.^[2]

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.^[3]

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.^{[4] [5]}

See also

• Quinacridone

Notes and References

1. 10.1021/ja00417a027. 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. 1976. Beak. Peter. Fry. Fred S.. Lee. Jaekeun. Steele. Frank. Journal of the American Chemical Society. 98. 171–179.
2. Acridone . C. F. H. Allen . G. H. W. McKee . amp . 19 . 6 . 10.15227/orgsyn.019.0006 . 1939. 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. Antimicrobial Agents and Chemotherapy . 1989 . 6–9 . 33. 1 . In Vitro and In Vivo Activities of Atalaphillinine and Related Acridone Alkaloids against Rodent Malaria . HISASHI FUJIOKA . YUKIHIRO NISHIYAMA . HIROSHI FURUKAWA . NOBUO KUMADA . amp . 2653215 . 171411 . 10.1128/aac.33.1.6.
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. . Discovery of dual function acridones as a new antimalarial chemotype . Nature . 2009 . 459 . 7244 . 270–273 . 10.1038/nature07937 . 19357645. 8158239 . 2009Natur.459..270K .