Acridone

Acridone

File:Acridone.svg
Names
Preferred IUPAC name Acridin-9(10H)-one
Other names 9-Acridanone
Identifiers
CAS Number	578-95-0 checkY
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:50756 checkY
ChEMBL	ChEMBL436589 checkY
ChemSpider	10188539 checkY
ECHA InfoCard
E number
PubChem CID	2015
UNII	6BK306GUQA checkY
CompTox Dashboard (EPA)	{{#property:P3117}}
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) 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
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 checkY☒N ?) Infobox references

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

Synthesis and structure

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

Acridone can be synthesized by heating fenamic acid.

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.

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.

See also

• Quinacridone