58995-74-7Relevant academic research and scientific papers
An iron(iii)-catalyzed dehydrogenative cross-coupling reaction of indoles with benzylamines to prepare 3-aminoindole derivatives
Chen, Wei-Li,Li, Kun,Liang, Cui,Liang, Wang-Fu,Liao, Wei-Cong,Mo, Dong-Liang,Qiu, Pei-Wen,Su, Gui-Fa
supporting information, p. 9610 - 9616 (2021/12/09)
We report a green cascade approach to prepare a variety of 3-aminoindole derivatives in good to excellent yields through an iron(iii)-catalyzed dehydrogenative cross-coupling reaction of 2-arylindoles and primary benzylamines under mild reaction conditions. Mechanistic studies show that a cascade reaction involves a tert-butyl nitrite (TBN)-mediated nitrosation of 2-substituted indoles and a 1,5-hydrogen shift to afford indolenine oximes, sequential iron(iii)-catalyzed condensation and a 1,5-hydrogen shift over four steps in a one-pot reaction. The reaction shows a broad substrate scope of indoles and benzylamines and tolerates a wide range of functional groups. Moreover, the reaction is easily performed at the gram scale without producing waste after the reaction is completed. The 3-aminoindole product is purified by simple extraction, washing, and recrystallization without flash column chromatography. A double imine ligand containing the 3-aminoindole unit is facile to obtain in a 52% yield in one step. The present method highlights readily available starting materials, a simple purification procedure, and the usage of cheap, nontoxic, and environmentally benign iron(iii) catalysts. This journal is
Novel Aryl Substituted Pyrazoles as Small Molecule Inhibitors of Cytochrome P450 CYP121A1: Synthesis and Antimycobacterial Evaluation
Taban, Ismail M.,Elshihawy, Hosam E. A. E.,Torun, Beyza,Zucchini, Benedetta,Williamson, Clare J.,Altuwairigi, Dania,Ngu, Adeline S. T.,McLean, Kirsty J.,Levy, Colin W.,Sood, Sakshi,Marino, Leonardo B.,Munro, Andrew W.,De Carvalho, Luiz Pedro S.,Simons, Claire
, p. 10257 - 10267 (2018/01/10)
Three series of biarylpyrazole imidazole and triazoles are described, which vary in the linker between the biaryl pyrazole and imidazole/triazole group. The imidazole and triazole series with the short -CH2- linker displayed promising antimycobacterial activity, with the imidazole-CH2- series (7) showing low MIC values (6.25-25 μg/mL), which was also influenced by lipophilicity. Extending the linker to -C(O)NH(CH2)2- resulted in a loss of antimycobacterial activity. The binding affinity of the compounds with CYP121A1 was determined by UV-visible optical titrations with KD values of 2.63, 35.6, and 290 μM, respectively, for the tightest binding compounds 7e, 8b, and 13d from their respective series. Both binding affinity assays and docking studies of the CYP121A1 inhibitors suggest type II indirect binding through interstitial water molecules, with key binding residues Thr77, Val78, Val82, Val83, Met86, Ser237, Gln385, and Arg386, comparable with the binding interactions observed with fluconazole and the natural substrate dicyclotyrosine.
Copper-catalyzed aerobic dehydrogenative cyclization of N-methyl-N-phenylhydrazones: Synthesis of cinnolines
Zhang, Guangwu,Miao, Jinmin,Zhao, Yan,Ge, Haibo
supporting information; experimental part, p. 8318 - 8321 (2012/09/07)
O2 leading the way: The title reaction proceeds through an oxidation/cyclization sequence, thus representing the first copper-catalyzed coupling reaction of hydrazones through a C sp 3-H bond functionalization process (see scheme; DMF=N,N'-dimethylformamide, Py=pyridine). The method provides an environmentally friendly and atom-efficient approach to biologically active cinnoline derivatives. Copyright
2-Phenyl-indole derivatives and process for preparing the same
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, (2008/06/13)
New stabilizers of polymers and co-polymers of vinyl chloride, the said stabilizers being 2-phenyl-indole derivatives corresponding to the formula: STR1 wherein R represents a phenyl radical, an amino group, optionally substituted by an acetyl or benzoyl
