Acridone is an organic compound based on the
acridine skeleton, with a carbonyl group at the ''9'' position. It is a yellow solid.
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 the condensation of
aniline
Aniline is an organic compound with the formula C6 H5 NH2. Consisting of a phenyl group attached to an amino group, aniline is the simplest aromatic amine
In organic chemistry, an aromatic amine is an organic compound consisting of an aroma ...
and
2-chlorobenzoic acid
2-Chlorobenzoic acid is an organic compound with the formula ClC6H4CO2H. It is one of three isomeric chlorobenzoic acids, the one that is the strongest acid. This white solid is used as a precursor to a variety of drugs, food additives, and dyes ...
and subsequently heating of
''N''-phenylanthranilic 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
Quinacridone is an organic compound used as a pigment. Numerous derivatives constitute the quinacridone pigment family, which finds extensive use in industrial colorant applications such as robust outdoor paints, inkjet printer ink, tattoo inks, ...
References
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Aromatic ketones