Acridone
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| Names | |
|---|---|
| Preferred IUPAC name
Acridin-9(10H)-one | |
| Other names
9-Acridanone | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.008.578 |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| 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).
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Acridone is an organic compound based on the acridine skeleton, with a carbonyl group at the 9 position.
Synthesis and structure
[edit]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
[edit]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
[edit]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
[edit]References
[edit]- ↑ 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
- ↑ Maier W, Baumert A, Schumann B, Furukawa H, Gröger D (1993). "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. Bibcode:1993PChem..32..691M. doi:10.1016/S0031-9422(00)95155-0.
- ↑ 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. PMC 171411. PMID 2653215.
- ↑ Kelly, Jane X.; Smilkstein, Martin J.; Brun, Reto; Wittlin, Sergio; Cooper, Roland A.; Lane, Kristin D.; Janowsky, Aaron; Johnson, Robert A.; Dodean, Rozalia A.; Winter, Rolf; Hinrichs, David J.; Riscoe, Michael K. (2009). "Discovery of dual function acridones as a new antimalarial chemotype". Nature. 459 (7244): 270–273. Bibcode:2009Natur.459..270K. doi:10.1038/nature07937. PMC 8158239. PMID 19357645.