- Microwave-promoted N-alkylation of acridones without solvent
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N-Alkylacridones (3) were effectively synthesized in few minutes by reaction of acridone and alkyl halides with NaOH/K2CO3 absorbed on Al2O3 in the presence of TBAB under microwave irradiation without solvent.
- Wang, Cunde,Hang, Tianlong,Zhang, Hui
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- Anisotropic Dissociation of π-π Stacking and Flipping-Motion-Induced Crystal Jumping in Alkylacridones and Their Dicyanomethylene Derivatives
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Ethylacridone (1 b) and dicyanomethylenated acridones 2 a,b,d showed crystal-jumping activity upon heating. This is the first example of thermosalient behavior in a simple aromatic ketone and its derivatives. A systematic investigation of the jumping behavior of derivatives with different alkyl chains by variable-temperature X-ray crystal-structure analyses revealed the mechanism of this phenomenon. Anisotropic dissociation of π stacking in a dimer was important for inducing crystal jumping in 1 b, whereas the collective fluctuation/flipping motion of a dicyanomethylene unit induced crystal jumping in 2.
- Takeda, Takashi,Akutagawa, Tomoyuki
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- Synthesis, cytotoxicity evaluation, and molecular modeling studies of 2,N10-substituted acridones as DNA-intercalating agents
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Acridine-based compounds possess anticancer activities by intercalating to DNA. Although they have chemotherapeutic potential, acridine-based compounds are not used to treat cancer. In this study, 2,N10-acridone derivatives are designed and synthesized based on acridone, a ketone derivative of acridine. Herein, acridone is functionalized with alkyl side chains containing terminal nitrogen-based moieties at the N10-position and substituted at the C2-position. The products are evaluated for in vitro cytotoxicity against four cancer cell lines: Molt-3, HepG2, A549, and HuCCA-1. The derivative bearing two butyl piperidine side chains at the C2- and N10-positions is the most active, with IC50 values ranging from 2.96 to 9.46 μM. Molecular modeling studies supported the binding of the derivatives to DNA by intercalation, thereby confirming the observed cytotoxic effects.
- Chimnoi, Nitirat,Eurtivong, Chatchakorn,Jumpathong, Watthanachai,Khunnawutmanotham, Nisachon,Techasakul, Supanna
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p. 410 - 425
(2020/03/23)
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- 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
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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
- Huang, Pang-Chi,Parthasarathy, Kanniyappan,Cheng, Chien-Hong
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supporting information
p. 460 - 464
(2013/02/23)
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- Preparation of Some New N-Substituted 9,10-Dihydroacridine Derivatives
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Some new 9,10-dihydroacridines were prepared owing to the well-known central nervous system activity of the structurally related tricyclic molecules.These compounds were easily obtained from 9(10H)-acridinones.
- Charbit, Jean Jacques,Galy, Anne Marie,Galy, Jean Pierre,Barbe, Jacques
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p. 136 - 137
(2007/10/02)
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- A Convenient Preparation of Some N-Alkylcarbazoles and N-Alkylacridones
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N-Alkylation of aromatic compounds involving nitrogen heterocycles such as carbazole and acridone with alkyl halide in the presence of caustic solution and benzyl triethyl ammonium chloride (BTEAC) as a phase-transfer catalyst readily proceeded under mild conditions.These results show that this procedure is effective for the preparation of the title compounds in high yields.
- Nishi, Hisao,Kohno, Hisao,Kano, Toshihiro
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p. 1897 - 1898
(2007/10/02)
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