76091-01-5Relevant academic research and scientific papers
Copper(I)/Copper(II)-Assisted Tandem Catalysis: The Case Study of Ullmann/Chan-Evans-Lam N1,N3-Diarylation of 3-Aminopyrazole
Beyer, Astrid,Castanheiro, Thomas,Busca, Patricia,Prestat, Guillaume
, p. 2433 - 2436 (2015/08/24)
Unprecedented CuI/CuII-assisted tandem catalysis allowing an Ullmann/Chan-Evans-Lam sequence was achieved. This three-component, one-pot reaction triggered by a change in the oxidation state of the metal leads to the selective N1,N3-diarylation of 3-aminopyrazole. This new method should be a valuable tool for small-molecule drug discovery that requires suitable regio- and/or chemoselective strategies for the N-arylation of nitrogen-containing heterocycles. Tandem power: The first assisted tandem copper-catalyzed process, triggered by a change in the oxidation state of the metal, is developed to allow a one-pot Ullman/Chan-Evans-Lam sequence leading to the selective N1,N3-diarylation of 3-aminopyrazole.
Regiocontrolled synthesis of 3- and 5-aminopyrazoles, pyrazolo[3,4-d] pyrimidines, pyrazolo[3,4-b]pyridines and pyrazolo[3,4-b]quinolinones as MAPK inhibitors
Bagley, Mark C.,Baashen, Mohammed,Paddock, Victoria L.,Kipling, David,Davis, Terence
, p. 8429 - 8438 (2013/09/02)
Microwave irradiation of a hydrazine and 3-methoxyacrylonitrile, ethoxymethylenemalononitrile or ethyl acetoacetate provides rapid access to 3- or 5-substituted pyrazoles in excellent yield and with total regiocontrol in a process that can be switched from one regioisomer to the other by choice of conditions. Subsequent reaction, either by microwave-assisted hydrolysis and cyclocondensation with formamide, Hantzsch-type three-component reaction with an aldehyde and ketone, or by cyclocondensation with 2-nitrobenzaldehyde, provides the pyrazolo[3,4-d]pyrimidine, pyrazolo[3,4-b]pyridine or pyrazolo[3,4-b] quinolin-4-one framework, respectively, of inhibitors of mitogen-activated protein kinases.
Novel 3-aminopyrazole inhibitors of MK-2 discovered by scaffold hopping strategy
Velcicky, Juraj,Feifel, Roland,Hawtin, Stuart,Heng, Richard,Huppertz, Christine,Koch, Guido,Kroemer, Markus,Moebitz, Henrik,Revesz, Laszlo,Scheufler, Clemens,Schlapbach, Achim
scheme or table, p. 1293 - 1297 (2010/06/15)
New, selective 3-aminopyrazole based MK2-inhibitors were discovered by scaffold hopping strategy. The new derivatives proved to inhibit intracellular phosphorylation of hsp27 as well as LPS-induced TNFα release in cells. In addition, selected derivative 1
