83318-14-3Relevant academic research and scientific papers
Copper-promoted one-pot approach: Synthesis of benzimidazoles
Adil, Syed Farooq,Alduhaish, Osamah,Assal, Mohamed E.,Bollikolla, Hari Babu,Gollapudi, Ravi Kumar,Murthy Boddapati, S. N.,Nurbasha, Sharmila,Siddiqui, Mohammed Rafiq H.,Tamminana, Ramana
, (2020/04/24)
A facile, one-pot, and proficient method was developed for the production of various 2-arylaminobenzimidazoles. This methodology is based for the first time on a copper catalyst promoted domino C-N cross-coupling reaction for the generation of 2-arylaminobenzimidazoles. Mechanistic investigations revealed that the synthetic pathway involves a copper-based desulphurization/nucleophilic substitution and a subsequent domino intra and intermolecular C-N cross-coupling reactions. Some of the issues typically encountered during the synthesis of 2-arylaminobezimidazoles, including the use of expensive catalytic systems and the low reactivity of bromo precursors, were addressed using this newly developed copper-catalyzed method. The reaction procedure is simple, generally with excellent substrate tolerance, and provides good to high yields of the desired products.
Novel synthesis of 2-aminobenzimidazoles from isoselenocyanates
Xie, Yuanyuan,Zhang, Fan,Li, Jianjun,Shi, Xiangjun
supporting information; experimental part, p. 901 - 904 (2010/07/06)
An efficient one-pot procedure for the synthesis of 2-aminobenzimidazoles from isoselenocyanates and various substituted diamines is described. Precipitation of elemental selenium from the reaction mixture greatly simplifies the purification procedure and also allows it to be re-used for preparation of isoseleno?cyanates. A possible mechanism for the formation of 2-aminobenzimidazoles is proposed. Georg Thieme Verlag Stuttgart - New York.
Structure-based design of novel 2-amino-6-phenyl-pyrimido[5′, 4′:5,6]pyrimido[1,2-a]benzimidazol-5(6H)-ones as potent and orally active inhibitors of lymphocyte specific kinase (Lck): Synthesis, SAR, and in vivo anti-inflammatory activity
Martin, Matthew W.,Newcomb, John,Nunes, Joseph J.,Boucher, Christina,Chai, Lilly,Epstein, Linda F.,Faust, Theodore,Flores, Sylvia,Gallant, Paul,Gore, Anu,Gu, Yan,Hsieh, Faye,Huang, Xin,Kim, Joseph L.,Middleton, Scot,Morgenstern, Kurt,Oliveira-dos-Santos, Antonio,Patel, Vinod F.,Powers, David,Rose, Paul,Tudor, Yanyan,Turci, Susan M.,Welcher, Andrew A.,Zack, Debra,Zhao, Huilin,Zhu, Li,Zhu, Xiaotian,Ghiron, Chiara,Ermann, Monika,Johnston, David,Saluste, Carl-Gustaf Pierre
, p. 1637 - 1648 (2008/12/22)
Lck, or lymphocyte specific kinase, is a cytoplasmic tyrosine kinase of the Src family expressed in T-cells and NK cells. Genetic evidence from knockout mice and human mutations demonstrates that Lck kinase activity is critical for T-cell receptor-mediated signaling, leading to normal T-cell development and activation. A small molecule inhibitor of Lck is expected to be useful in the treatment of T-cell-mediated autoimmune and inflammatory disorders and/or organ transplant rejection. In this paper, we describe the structure-guided design, synthesis, structure-activity relationships, and pharmacological characterization of 2-amino-6-phenylpyrimido[5′,4′:5,6]pyrimido[1,2- a]benzimidazol-5(6H)-ones, a new class of compounds that are potent inhibitors of Lck. The most promising compound of this series, 6-(2,6-dimethylphenyl)-2- ((4-(4-methyl-1-piperazinyl)phenyl)amino)pyrimido[5′,4′:5,6] pyrimido-[1,2-a]benzimidazol-5(6H)-one (25), exhibits potent inhibition of Lck kinase activity. This activity translates into inhibition of in vitro cell-based assays and in vivo models of T-cell activation and arthritis, respectively.
