Acridone

Chemical compound From Wikipedia, the free encyclopedia

Acridone is an organic compound based on the acridine skeleton, with a carbonyl group at the 9 position.

Quick facts Names, Identifiers ...
Acridone
Names
Preferred IUPAC name
Acridin-9(10H)-one
Other names
9-Acridanone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.578 Edit this at Wikidata
UNII
  • 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) checkY
    Key: FZEYVTFCMJSGMP-UHFFFAOYSA-N checkY
  • 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
  • C1=CC=C2C(=C1)C(=O)C3=CC=CC=C3N2
  • O=C1c3ccccc3Nc2ccccc12
Properties
C13H9NO
Molar mass 195.221 g·mol−1
Appearance yellow powder
Melting point 250 °C (482 °F; 523 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis and structure

The molecule is planar. Optical spectra reveal that the keto tautomer predominates in the gas-phase and in ethanol solution.[1]

Acridone can be synthesized by heating fenamic acid.[2]

History

One of the first who were able to prove the compound's existence was Karl Drechsler, Student of G. Goldschmiedt, at the k.u.k. Universität Wien (Vienna, Austria) in 1914.[3]

Derivatives

Acridone constitutes the scaffold of some synthetic compounds with diverse pharmacological activities. 3-Chloro-6-(2-diethylamino-ethoxy)-10-(2-diethylamino-ethyl)-acridone has shown promise as an antimalarial drug.[4][5]

See also

References

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