Acridone

Acridone
Names
Preferred IUPAC name
Acridin-9(10H)-one
Other names
9-Acridanone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.578 Edit this at Wikidata
UNII
  • 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) checkY
    Key: FZEYVTFCMJSGMP-UHFFFAOYSA-N checkY
  • 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
  • C1=CC=C2C(=C1)C(=O)C3=CC=CC=C3N2
  • O=C1c3ccccc3Nc2ccccc12
Properties
C13H9NO
Molar mass 195.221 g·mol−1
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 [77 °F], 100 kPa).
X markN verify (what is checkYX markN ?)

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 itself can be synthesized by heating fenamic acid.

Acridones in general can be synthesized by several routes. One classic method for the synthesis of acridones is the Lehmstedt–Tanasescu reaction, a reaction between a 2-nitrobenzaldehyde (1) and an arene compound (2) in the presence of an acidic nitrous acid:

The Lehmstedt–Tanasescu reaction

In enzymology, an acridone synthase (EC 2.3.1.159) is an enzyme that catalyzes the chemical reaction

3 malonyl-CoA + N-methylanthraniloyl-CoA ⇌ 4 CoA + 1,3-dihydroxy-N-methylacridone + 3 CO2

Thus, the two substrates of this enzyme are malonyl-CoA and N-methylanthraniloyl-CoA, whereas its three products are CoA, 1,3-dihydroxy-N-methylacridone, and CO2.

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. ↑ Yoshida, Shu (1997). Design, Synthesis and Characterization of Novel Heterocyclic Polymers (PhD thesis). McGill University, Montreal, Canada.
  4. ↑ Ion Tănăsescu Bull Soc Chim Fr 41 (1927) p. 528
  5. ↑ Lehmstedt, Kurt (1932). "Eine einfache Synthese des Acridons und 3-substituierter Acridone (IX. Mitteil. über Acridin)". Berichte der Deutschen Chemischen Gesellschaft (A and B Series). 65 (5): 834–839. doi:10.1002/cber.19320650531.
  6. ↑ I Silberg. Rev Roum Chim 10 (1965) 1035
  7. ↑ Maier W, Baumert A, Schumann B, Furukawa H, Gröger D (1993). "Synthesis of 1,3-dihydroxy-N-methylacridone and its conversion to rutacridone by cell-free extracts of Ruta-graveolens cell cultures". Phytochemistry. 32 (3): 691–698. Bibcode:1993PChem..32..691M. doi:10.1016/S0031-9422(00)95155-0.
  8. ↑ Austrian National Library, Reports of the monthly meetings of the Academy of Sciences
  9. ↑ 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.
  10. ↑ 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.