Acridone

Acridone is an organic compound based on the acridine skeleton, with a carbonyl group at the 9 position. A yellow solid.

Acridone
Names
IUPAC name
10H-Acridin-9-one
Other names
9-Acridanone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.578
UNII
Properties
C13H9NO
Molar mass 195.221 g·mol−1
Appearance yellow solid
Melting point 250 °C (482 °F; 523 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

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 the condensation of aniline and 2-chlorobenzoic acid. It can also be prepared by heating N-phenylanthranilic 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

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. doi:10.1038/nature07937. PMID 19357645.
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