13082-16-1Relevant academic research and scientific papers
Synthesis of novel heme-interacting acridone derivatives to prevent free heme-mediated protein oxidation and degradation
Pal, Chinmay,Kundu, Milan Kumar,Bandyopadhyay, Uday,Adhikari, Susanta
, p. 3563 - 3567 (2011)
Heme is an important prosthetic molecule for various hemoproteins and serves important function in living aerobic organisms. But degradation of hemoprotein, for example, hemoglobin during different pathological conditions leads to the release of heme, which is very toxic as it induces oxidative stress and inflammation due to its pro-oxidant nature. Thus, synthesis of compound that will detoxify free heme by interacting with it would be fruitful for the management of heme-induced pathogenesis. Here, we report the synthesis of a novel natural product arborinine and some other acridone derivatives, which interact with free heme. These acridones in vitro block heme-mediated protein oxidation and degradation, markers for heme-induced oxidative stress.
Natural Product Chemistry, Part 137: Oxidation of Acridone Alkaloids: Synthesis of 5-Methoxyacronycine
Reisch, Johannes,Wickramasinghe, Anura
, p. 709 - 712 (1990)
Epoxidation of acridone alkaloid acronycine (1) resulted in hydroxylation at the aromatic ring giving 5-hydroxyacronycine (3).The same reaction on 1,3-dimethoxy-10-methyl-9(10H)-acridone (5) gave 1,3-dimethoxy-2-hydroxy-10-methyl-9(10H)-acridone (6), 1,3-dimethoxy-2-hydroxy-4-peroxy-10-methyl-9(10H)-acridone (8), and 1,3-dimethoxy-2,4-diperoxy-10-methyl-9(10H)-acridone (9).
Copper-catalyzed intramolecular oxidative C-H functionalization and C-N formation of 2-aminobenzophenones: Unusual pseudo-1,2-shift of the substituent on the aryl ring
Huang, Pang-Chi,Parthasarathy, Kanniyappan,Cheng, Chien-Hong
, p. 460 - 464 (2013/02/23)
A good move: A copper-catalyzed intramolecular oxidative C-H functionalization of 2-aminobenzophenone affords two regioisomeric acridones (see scheme). The reaction involves an unusual pseudo-1,2-migration of R 2 group(s) on the arene ring (bpy=2,2-bipyridine, DMAc=dimethylacetimide). Copyright
Use of N-lithiated ethyl anthranilates as 1,4-dipole equivalents in 1,4-dipole-aryne cycloaddition: a novel approach to the synthesis of acridones
Khanapure,Bhawal,Biehl
, p. 2869 - 2972 (2007/10/02)
A new strategy for acridones based on 1,4-dipolar cycloaddition of N-lithiated ethyl anthranilates, which function as 1,4-dipole equivalents, with arynes is reported.
The Chemistry of 2H-3,1-Benzoxazine-2,4(1H)-dione (Isatoic Anhydride). 21. A Mild Process For The Preparation of 10-Alkyl-9-acridanones And It's Application To The Synthesis of Acridone Alkaloids
Coppola, Gary M.,Schuster, Herbert F.
, p. 957 - 964 (2007/10/02)
10-Substituted-9-acridanones are readily prepared by the reaction of the corresponding isatoic anhydride with the lithium enolate of 2-cyclohexen-1-one.The initially formed product, the 1,2-dihydroacridone need not be purified but can be aromatized directly with DDQ to the desired acridone.This methodology is applicable to the synthesis of acridone natural products.Two alkaloids, 1,2,3-trimethoxy-10-methylacridone (9) and evoxanthine (10), were prepared from 4,5,6-trimethoxy-N-methylisatoic anhydride and 6-methoxy-4,5-methylenedioxy-N-methylisatoic anhydride respectively.In these trioxygenated systems, palladium-on-charcoal must be used to aromatize the penultimate intermediate.
