Acridone

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

Acridone

Names
Preferred IUPAC name Acridin-9(10H)-one
Other names 9-Acridanone
Identifiers
CAS Number	578-95-0 Y
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:50756 Y
ChEMBL	ChEMBL436589 Y
ChemSpider	10188539 Y
ECHA InfoCard	100.008.578
PubChem CID	2015
UNII	6BK306GUQA Y
CompTox Dashboard (EPA)	DTXSID8060371
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) Y Key: FZEYVTFCMJSGMP-UHFFFAOYSA-N Y 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−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). N verify (what is YN ?) Infobox references

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

• Quinacridone