Acridone

Acridone

Names
IUPAC name 10H-acridin-9-one
Identifiers
CAS Number	578-95-0
ChEBI	CHEBI:50756
ChEMBL	ChEMBL436589
ChemSpider	10188539
Jmol interactive 3D	Image Image
PubChem	2015
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	195.22 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Acridone is an organic compound based on the acridine skeleton, with a carbonyl group at the 9 position. It may be synthesized by the self-condensation of N-phenylanthranilic acid.^[1]

Derivatives

Acridone constitutes the scaffold of some synthetic compounds with various pharmacological activities. Most recent derivatives still in its development stage, including 3-chloro-6-(2-diethylamino-ethoxy)-10-(2-diethylamino-ethyl)-acridone, have shown some promise as a potential antimalarial drugs.^[2][3]

2-chloroacridone is the precursor used to make clomacran (tranquilizer).

References

1. C. F. H. Allen and G. H. W. McKee (1943). "Acridone". Org. Synth.; Coll. Vol. 2, p. 15
2. HISASHI FUJIOKA, YUKIHIRO NISHIYAMA, HIROSHI FURUKAWA, AND 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.
3. 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.