462068-77-5Relevant academic research and scientific papers
Identification of Potent Indoleamine 2,3-Dioxygenase 1 (IDO1) Inhibitors Based on a Phenylimidazole Scaffold
Brant, Michael G.,Goodwin-Tindall, Jake,Stover, Kurt R.,Stafford, Paul M.,Wu, Fan,Meek, Autumn R.,Schiavini, Paolo,Wohnig, Stephanie,Weaver, Donald F.
, p. 131 - 136 (2018)
Inhibition of indoleamine 2,3-dioxygenase (IDO1) is an attractive immunotherapeutic approach for the treatment of a variety of cancers. Dysregulation of this enzyme has also been implicated in other disorders including Alzheimer's disease and arthritis. Herein, we report the structure-based design of two related series of molecules: N1-substituted 5-indoleimidazoles and N1-substituted 5-phenylimidazoles. The latter (and more potent) series was accessed through an unexpected rearrangement of an imine intermediate during a Van Leusen imidazole synthesis reaction. Evidence for the binding modes for both inhibitor series is supported by computational and structure-activity relationship studies.
Synthesis of Azepino[1,2-a]indole-10-amines via [6+1] Annulation of Ynenitriles with Reformatsky Reagent
Iioka, Ryoya,Yorozu, Kohei,Sakai, Yoko,Kawai, Rika,Hatae, Noriyuki,Takashima, Katsuki,Tanabe, Genzoh,Wasada, Hiroaki,Yoshimatsu, Mitsuhiro
supporting information, p. 1553 - 1558 (2021/02/26)
Lewis acid-catalyzed [6+1] annulation reactions of 2-cyano-1-propargyl- and 2-alkynyl-1-cyanomethyl-indoles with Reformatsky reagent are described. 8-Aryl, 8-alkyl-, 8-hetaryl-, 9-aryl, and 9-alkyl-azepino[1,2-a]indole amines were obtained through a 7-endo-mode cyclization of the β-aminoacrylate intermediates. The antiproliferative activity of the azepino[1,2-a]indoles analogs against the HCT-116 cells were also examined.
Synthesis of new highly functionalized 1h-indole-2-carbonitriles via cross-coupling reactions
Hrizi, Asma,Cailler, Manon,Romdhani-Younes, Moufida,Carcenac, Yvan,Thibonnet, Jér?me
, (2021/09/06)
An approach for the preparation of polysubstituted indole-2-carbonitriles through a cross-coupling reaction of compounds 1-(but-2-ynyl)-1H-indole-2-carbonitriles and 1-benzyl-3-iodo-1H-indole-2-carbonitriles is described. The reactivity of indole derivatives with iodine at position 3 was studied using cross-coupling reactions. The Sonogashira, Suzuki–Miyaura, Stille and Heck cross-couplings afforded a variety of di-, tri-and tetra-substituted indole-2-carbonitriles.
Indole-2-carboxamidines as novel NR2B selective NMDA receptor antagonists
Borza, Istvan,Kolok, Sandor,Ignacz-Szendrei, Gyoergyi,Greiner, Istvan,Tarkanyi, Gabor,Galgoczy, Kornel,Horvath, Csilla,Farkas, Sandor,Domany, Gyoergy
, p. 5439 - 5441 (2007/10/03)
A novel series of indole-2-carboxamidine derivatives was prepared and identified as NR2B selective NMDA receptor antagonists. The influence of the substituents on the indole skeleton as well as the substitution of the benzyl moiety on the biological activ
