- An efficient route to synthesize isatins by metal-free, iodine-catalyzed sequential C(sp3)-H oxidation and intramolecular C-N bond formation of 2′-aminoacetophenones
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A novel molecular I2-catalyzed synthesis of isatins through C(sp3)-H oxidation and intramolecular C-N bond formation of 2′-aminoacetophenones with excellent yields up to 97% under transition metal, base, additive, peroxide and ligand free conditions is described. The present protocol is suitable for gram scale synthesis of isatins and retained its high yield. Further, the synthetic utility of this present reaction towards synthesis of bioactive 3-hydroxy-2-oxindoles and oxindoles is demonstrated. This journal is
- Rajeshkumar, Venkatachalam,Chandrasekar, Selvaraj,Sekar, Govindasamy
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- Design, synthesis and evaluation of N-aryl-glyoxamide derivatives as structurally novel bacterial quorum sensing inhibitors
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Bacteria cooperatively regulate the expression of many phenotypes through a mechanism called quorum sensing (QS). Many Gram-negative bacteria use an N-acyl homoserine lactone (AHL)-mediated QS system to control biofilm formation and virulence factor production. In recent years, quorum sensing inhibitors (QSIs) have become attractive tools to overcome antimicrobial resistance exhibited by various pathogenic bacteria. In the present study, we report the design and synthesis of novel N-arylisatin-based glyoxamide derivatives via the ring-opening reaction of N-aryl isatins with cyclic and acylic amines, and amino acid esters. The QSI activity of the synthesized compounds was determined in the LasR-expressing Pseudomonas aeruginosa MH602 and LuxR-expressing Escherichia coli MT102 reporter strains. Compounds 31 and 32 exhibited the greatest QSI activity in P. aeruginosa MH602, with 48.7% and 42.7% reduction in QS activity at 250 μM, respectively, while compounds 31 and 34 showed 73.6% and 43.7% QSI activity in E. coli MT102. In addition, the ability of these compounds to inhibit the production of pyocyanin in P. aeruginosa (PA14) was also determined, with compound 28 showing 47% inhibition at 250 μM. Furthermore, computational docking studies were performed on the LasR receptor protein of P. aeruginosa, which showed that formation of a hydrogen bonding network played a major role in influencing the QS inhibitory activity. We envisage that these novel non-AHL glyoxamide derivatives could become a new tool for the study of QS and potentially for the treatment of bacterial infections.
- Nizalapur, Shashidhar,Kimyon, ?nder,Biswas, Nripendra Nath,Gardner, Christopher R.,Griffith, Renate,Rice, Scott A.,Manefield, Mike,Willcox, Mark,Black, David StC.,Kumar, Naresh
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p. 680 - 693
(2016/01/12)
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- Design, synthesis and biological evaluation of N-alkyl or aryl substituted isoindigo derivatives as potential dual cyclin-dependent kinase 2 (CDK2)/glycogen synthase kinase 3β (GSK-3β) phosphorylation inhibitors
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A series of N-alkyl or aryl substituted isoindigo derivatives have been synthesized and their anti-proliferative activity was evaluated by Sulforhodamine B (SRB) assay. Some of the target compounds exhibited significant antitumor activity, including compounds 6h and 6k (against K562 cells), 6i (against HeLa cells) and 6j (against A549 cells). N-(p-methoxy-phenyl)-isoindigo (6k) exhibited a high and selective anti-proliferative activity against K562 cells (IC50 7.8 μM) and induced the apoptosis of K562 cells in a dose-dependent manner. Compound 6k arrested the cell cycle at S phase in K562 cells by decreasing the expression of cyclin A and CDK2, which played critical roles in DNA replication and passage through G2 phase. Moreover, compound 6k down-regulated the expression of p-GSK-3β (Ser9), β-catenin and c-myc proteins, up-regulated the expression of GSK-3β, consequently, suppressed Wnt/β-catenin signaling pathway and induced the apoptosis of K562 cells. The binding mode of compound 6k with GSK-3β was simulated using molecular docking tools. All of these studies gave a better understanding to the molecular mechanisms of this class of agents and clues to develop dual CDK2/GSK-3β (Ser9) phosphorylation inhibitors applied in cancer chemotherapy.
- Zhao, Ping,Li, Yanzhong,Gao, Guangwei,Wang, Shuai,Yan, Yun,Zhan, Xiaoping,Liu, Zenglu,Mao, Zhenmin,Chen, Shaoxiong,Wang, Liqun
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p. 165 - 174
(2014/09/17)
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- Selenium-promoted intramolecular oxidative amidation of 2-(arylamino)acetophenones for the synthesis of N-arylisatins
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A convenient method for the synthesis of N-arylisatins from 2-(arylamino)acetophenones by using SeO2 as an oxidant is described. Various substituted N-arylisatins were selectively obtained in good to excellent yields. The reaction tolerates a wide range of functionalities. Copyright
- Liu, Yong,Chen, Hui,Hu, Xiong,Zhou, Wang,Deng, Guo-Jun
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p. 4229 - 4232
(2013/07/26)
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- Cu(i)-catalyzed intramolecular oxidative C-H amination of 2-aminoacetophenones: A convenient route toward isatins
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2-Aminoaryl methyl ketones undergo intramolecular oxidative C-H amination to give the corresponding substituted isatins under an oxygen atmosphere in the presence of [CuI(bpy)]2. The Royal Society of Chemistry 2013.
- Huang, Pang-Chi,Gandeepan, Parthasarathy,Cheng, Chien-Hong
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supporting information
p. 8540 - 8542
(2013/09/23)
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- Synthesis of N-arylisatins using different heterogeneous catalyst under microwave irradiations
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N-Arylisatins having both biological and medical properties are synthesized by the reaction of methyl-2-oxo-2-(arylamino)acetates and arynes using NaHCO3 in presence of different heterogeneous catalyst under microwave irradiations in high yield in shorter
- Singh, Ravinder,Kumar, Ramesh
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p. 4935 - 4938
(2013/07/28)
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- Synthesis of n-arylisatins using nay heterogeneous catalyst under microwave irradiations
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N-Arylisatins are synthesized in high yield in shorter reaction time by the reaction of 2-oxo-2-(Arylamino)acetates and arynes using NaY heterogeneous catalyst under microwave irradiations.
- Singh, Ravinder,Kumar, Ramesh
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p. 1049 - 1054
(2012/10/29)
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- Convenient syntheses of benzo-fluorinated dibenz[b,f]azepines: Rearrangements of isatins, acridines, and indoles
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Efficient procedures for the synthesis of benzo-fluorinated dibenz[b,f]azepines (iminostilbenes) from fluorinated isatins or indoles using a number of ring-expansion reactions are described. A range of mono- and difluorinated analogues is accessible, and the syntheses can deliver gram quantities of the final products, which are precursors of fluoro analogues of the important anticonvulsant carbamazepine.
- Elliott, Emma-Claire,Bowkett, Elizabeth R.,Maggs, James L.,Bacsa, John,Park, B. Kevin,Regan, Sophie L.,O'Neill, Paul M.,Stachulski, Andrew V.
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supporting information; experimental part
p. 5592 - 5595
(2011/12/03)
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- Synthesis of N -arylisatins by the reaction of arynes with methyl 2-Oxo-2-(arylamino)acetates
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N-Arylisatins are efficiently prepared by the reaction of 2-oxo-2-(arylamino)acetates and arynes under mild reaction conditions
- Rogness, Donald C.,Larock, Richard C.
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experimental part
p. 4980 - 4986
(2011/08/06)
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- N-Arylation of Isatins. A Direct Route to N-Arylisatoic Anhydrides
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The synthesis of N-arylisatoic anhydrides 3 has been accomplished by using a two-step process.The key reaction in the sequence is the direct N-arylation of isatin with an aryl bromide in the presence of cupric oxide.Subsequent oxidation of the resulting N
- Coppola, Gary M.
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p. 1249 - 1251
(2007/10/02)
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