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Acridone

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Acridone
Names
IUPAC name 10H-acridin-9-one
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.578 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
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 195.221 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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.

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.

References

  1. C. F. H. Allen and G. H. W. McKee (1943). "Acridone". Organic Syntheses; Collected Volumes, 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. PMC 171411. PMID 2653215.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
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