Acridone

Acridone

Names
IUPAC name 10H-acridin-9-one
Identifiers
CAS Number	578-95-0
3D model (Jmol)	Interactive image Interactive image
ChEBI	CHEBI:50756
ChEMBL	ChEMBL436589
ChemSpider	10188539
ECHA InfoCard	100.008.578
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; G. H. W. McKee (1943). "Acridone". Org. Synth.; Coll. Vol., 2, p. 15
2. 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.
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.