139944-70-0Relevant articles and documents
Discovery and Characterization of CD12681, a Potent RORγ Inverse Agonist, Preclinical Candidate for the Topical Treatment of Psoriasis
Ouvry, Gilles,Atrux-Tallau, Nicolas,Bihl, Franck,Bondu, Aline,Bouix-Peter, Claire,Carlavan, Isabelle,Christin, Olivier,Cuadrado, Marie-Josée,Defoin-Platel, Claire,Deret, Sophie,Duvert, Denis,Feret, Christophe,Forissier, Mathieu,Fournier, Jean-Fran?ois,Froude, David,Hacini-Rachinel, Fériel,Harris, Craig Steven,Hervouet, Catherine,Huguet, Hélène,Lafitte, Guillaume,Luzy, Anne-Pascale,Musicki, Branislav,Orfila, Danielle,Ozello, Benjamin,Pascau, Coralie,Pascau, Jonathan,Parnet, Véronique,Peluchon, Guillaume,Pierre, Romain,Piwnica, David,Raffin, Catherine,Rossio, Patricia,Spiesse, Delphine,Taquet, Nathalie,Thoreau, Etienne,Vatinel, Rodolphe,Vial, Emmanuel,Hennequin, Laurent Fran?ois
, p. 321 - 337 (2018)
With possible implications in multiple autoimmune diseases, the retinoic acid receptor-related orphan receptor RORγ has become a sought-after target in the pharmaceutical industry. Herein are described the efforts to identify a potent RORγ inverse agonist compatible with topical application for the treatment of skin diseases. These efforts culminated in the discovery of N-(2,4-dimethylphenyl)-N-isobutyl-2-oxo-1-[(tetrahydro-2H-pyran-4-yl)methyl]-2,3-dihydro-1H-benzo[d]imidazole-5-sulfonamide (CD12681), a potent inverse agonist with in vivo activity in an IL-23-induced mouse skin inflammation model.
Catalytic Selective Oxidative Coupling of Secondary N-Alkylanilines: An Approach to Azoxyarene
Ke, Lei,Zhu, Guirong,Qian, Hui,Xiang, Guangya,Chen, Qin,Chen, Zhilong
supporting information, p. 4008 - 4013 (2019/06/04)
Azoxyarenes are among important scaffolds in organic molecules. Direct oxidative coupling of primary anilines provides a concise fashion to construct them. However, whether these scaffolds can be prepared from secondary N-alkylanilines is not well explored. Here, we present a catalytic selective oxidative coupling of secondary N-alkylaniline to afford azoxyarene with tungsten catalyst under mild conditions. In addition, azoxy can be viewed as a bioisostere of alkene and amide. Several "azoxyarene analogues" of the corresponding bioactive alkenes and amides showed comparable promising anticancer activities.
Arylation of Amines in Alkane Solvents by using Well-Defined Palladium-N-Heterocyclic Carbene Complexes
Marelli, Enrico,Chartoire, Anthony,Le Duc, Gaetan,Nolan, Steven P.
, p. 4021 - 4024 (2015/12/26)
The use of the ITent-based series of Pd-N-heterocyclic carbenes precatalysts (Tent= Tentacular) enables the Buchwald-Hartwig amine arylation reaction in apolar alkane solvents. The use of such solvents is rare because of their poor solvation properties. Nonetheless, they could be of interest for industrial applications, as they can be disposed of in an energetically favorable manner and may potentially simplify product isolation. The excellent solubility of the precatalysts permitted the desired products to be obtained in yields ranging from 75 to 96 %, even with deactivated and functionalized coupling partners. Fueling cross-couplings: The use of ITent-based Pd precatalysts (Tent=tentacular) enables the Buchwald-Hartwig amine arylation reaction in alkane solvents. Such solvents could be of interest for industrial applications, as they can be disposed of in an energetically favorable manner and may potentially simplify product isolation. Yields ranging from 75 to 96 % are obtained, even with challenging substrates.
