Acridone

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Acridone
Acridone.png
Names
IUPAC name
10H-acridin-9-one
Identifiers
578-95-0 N
ChEBI CHEBI:50756 YesY
ChEMBL ChEMBL436589 YesY
ChemSpider 10188539 YesY
Jmol 3D model Interactive image
Interactive image
PubChem 2015
Properties
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[edit]

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[edit]

  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 171411free to read. 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.