Acridone

Acridone
IUPAC name

10H-acridin-9-one
Identifiers
CAS number 578-95-0 Y
PubChem 2015
ChemSpider 10188539 Y
ChEBI CHEBI:50756 Y
ChEMBL CHEMBL436589 Y
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C13H9NO
Molar mass 195.22 g mol−1
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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]

References

  1. ^ C. F. H. Allen and G. H. W. McKee (1943), "Acridone", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv2p0015 ; Coll. Vol. 2: 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. PMC 171411. PMID 2653215. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=171411. 
  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.