Chemistry:Acridone
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.[1]
Acridone itself can be synthesized by heating fenamic acid.[2]
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:[3][4][5][6]
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.[7]
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.[8]
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.[9][10]
See also
References
- ↑ Beak, Peter; Fry, Fred S.; Lee, Jaekeun; Steele, Frank (1976). "Equilibration studies. Protomeric equilibria of 2- and 4-hydroxypyridines, 2- and 4-hydroxypyrimidines, 2- and 4-mercaptopyridines, and structurally related compounds in the gas phase". Journal of the American Chemical Society 98: 171–179. doi:10.1021/ja00417a027.
- ↑ C. F. H. Allen; G. H. W. McKee (1939). "Acridone". Organic Syntheses 19: 6. doi:10.15227/orgsyn.019.0006.
- ↑ Yoshida, Shu (1997). Design, Synthesis and Characterization of Novel Heterocyclic Polymers (PhD thesis). McGill University, Montreal, Canada.
- ↑ Ion Tănăsescu Bull Soc Chim Fr 41 (1927) p. 528
- ↑ Lehmstedt, Kurt (1932). "Eine einfache Synthese des Acridons und 3-substituierter Acridone (IX. Mitteil. über Acridin)". Berichte der Deutschen Chemischen Gesellschaft (A and B Series) 65 (5): 834–839. doi:10.1002/cber.19320650531.
- ↑ I Silberg. Rev Roum Chim 10 (1965) 1035
- ↑ "Synthesis of 1,3-dihydroxy-N-methylacridone and its conversion to rutacridone by cell-free extracts of Ruta-graveolens cell cultures". Phytochemistry 32 (3): 691–698. 1993. doi:10.1016/S0031-9422(00)95155-0. Bibcode: 1993PChem..32..691M.
- ↑ Austrian National Library, Reports of the monthly meetings of the Academy of Sciences
- ↑ HISASHI FUJIOKA; YUKIHIRO NISHIYAMA; HIROSHI FURUKAWA; NOBUO KUMADA (1989). "In Vitro and In Vivo Activities of Atalaphillinine and Related Acridone Alkaloids against Rodent Malaria". Antimicrobial Agents and Chemotherapy 33 (1): 6–9. doi:10.1128/aac.33.1.6. PMID 2653215.
- ↑ Kelly, Jane X.; Smilkstein, Martin J.; Brun, Reto; Wittlin, Sergio; Cooper, Roland A.; Lane, Kristin D.; Janowsky, Aaron; Johnson, Robert A. et al. (2009). "Discovery of dual function acridones as a new antimalarial chemotype". Nature 459 (7244): 270–273. doi:10.1038/nature07937. PMID 19357645. Bibcode: 2009Natur.459..270K.
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