5489-57-6Relevant academic research and scientific papers
Weakly Coordinating, Ketone-Directed (η5-Pentamethylcyclopentadienyl)cobalt(III)- and (η5-Pentamethylcyclopentadienyl)rhodium(III)-Catalyzed C?H Amidation of Arenes: A Route to Acridone Alkaloids
Bera, Sourav Sekhar,Sk, Md Raja,Maji, Modhu Sudan
supporting information, p. 1806 - 1811 (2019/01/14)
The weakly coordinating, ketone-directed, regioselective monoamidation of aromatic ketones, chalcone, carbazole, and benzophenones was achieved by employing high-valent cobalt and rhodium catalysis to access numerous biologically important molecular building blocks. This amidation proceeded smoothly with a variety of ketones and several amidating partners. The application of the products in the synthesis of various heterocycles, including acridones, indoles, quinoline, quinolones, quinolinones, and quinazolines, was also explored. The total synthesis of acridone-based alkaloids, namely, toddaliopsin A, toddaliopsin D, and arborinine, and the formal synthesis of acronycine and noracronycin were also accomplished by applying this method. A mechanistic study revealed this amidation reaction follows a base-assisted intermolecular electrophilic substitution pathway.
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
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 (2011/08/06)
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.
