Acridone
Chemical compound
Acridone is an organic compound based on the acridine skeleton, with a carbonyl group at the 9 position.
01Synthesis 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:
In enzymology, an acridone synthase (EC 2.3.1.159) 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.
02History
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.
03Derivatives
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.
Sources and credits
This article is adapted from the Wikipedia article “Acridone”, written by its contributors and licensed under CC BY-SA 4.0. Fathomly has changed the layout, removed citation markers, navigation and maintenance notices, and adjusted punctuation. This adapted version is shared under the same license. For references, see the original article.
Images, from Wikimedia Commons:
- Acridone.svg by User:Edgar181, Public domain
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