949928-08-9Relevant academic research and scientific papers
1,2-Disubstituted Benzimidazoles by the Iron Catalyzed Cross-Dehydrogenative Coupling of Isomeric o-Phenylenediamine Substrates
Foss, Frank W.,Palacios, Philip M.,Pierce, Brad S.,Thapa, Pawan,Tran, Tam
, p. 1991 - 2009 (2020/03/13)
Benzimidazoles are common in nature, medicines, and materials. Numerous strategies for preparing 2-arylbenzimidazoles exist. In this work, 1,2-disubstituted benzimidazoles were prepared from various mono- and disubstituted ortho-phenylenediamines (OPD) by iron-catalyzed oxidative coupling. Specifically, O2 and FeCl3·6H2O catalyzed the cross-dehydrogenative coupling and aromatization of diarylmethyl and dialkyl benzimidazole precursors. N,N′-Disubstituted-OPD substrates were significantly more reactive than their N,N-disubstituted isomers, which appears to be relative to their propensity for complexation and charge transfer with Fe3+. The reaction also converted N-monosubstituted OPD substrates to 2-substituted benzimidazoles; however, electron-poor substrates produce 1,2-disubstituted benzimidazoles by intermolecular imino-transfer. Kinetic, reagent, and spectroscopic (UV-vis and EPR) studies suggest a mechanism involving metal-substrate complexation, charge transfer, and aerobic turnover, involving high-valent Fe(IV) intermediates. Overall, comparative strategies for the relatively sustainable and efficient synthesis of 1,2-disubstituted benzimidazoles are demonstrated.
Benzimidazole- and indole-substituted 1,3′-bipyrrolidine benzamides as histamine H3 receptor antagonists
Cole, Derek C.,Gross, Jonathan L.,Comery, Thomas A.,Aschmies, Suzan,Hirst, Warren D.,Kelley, Cody,Kim, Ji-In,Kubek, Katie,Ning, Xiaoping,Platt, Brian J.,Robichaud, Albert J.,Solvibile, William R.,Stock, Joseph R.,Tawa, Gregory,Williams, Marla J.,Ellingboe, John W.
scheme or table, p. 1237 - 1240 (2010/06/15)
Using a focused screen of biogenic amine compounds we identified a novel series of H3R antagonists. A preliminary SAR study led to reduction of MW while increasing binding affinity and potency. Optimization of the physical properties of the ser
N-substituted-azacyclylamines as histamine-3 antagonists
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Page/Page column 12, (2010/11/28)
The present invention provides a compound of formula I and the use thereof for the treatment of a central nervous system disorder related to or affected by the histamine-3 receptor.
