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 itself can be synthesized by heating fenamic acid.
Acridones in general can be synthesized by several routes. One classic method for the synthesis of acridones is the Lehmstedt–Tanasescu reaction, a reaction between a 2-nitrobenzaldehyde (1) and an arene compound (2) in the presence of an acidic nitrous acid:Ion Tănăsescu Bull Soc Chim Fr 41 (1927) p. 528I Silberg. Rev Roum Chim 10 (1965) 1035
In enzymology, an acridone synthase () is an enzyme that catalyzes the chemical reaction
3 malonyl-CoA + N-methylanthraniloyl-CoA 4 CoA + 1,3-dihydroxy-N-methylacridone + 3 CO2
Thus, the two substrates of this enzyme are malonyl-CoA and N-methylanthraniloyl-CoA, whereas its three products are CoA, 1,3-dihydroxy-N-methylacridone, and CO2.
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.Austrian National Library, Reports of the monthly meetings of the Academy of Sciences
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
References