53704-77-1

Upstream product

• 100-39-0 benzyl bromide 
• 4335-28-8 2,3-diidro-6-fenilimidazo<2,1-b>tiazolo 
• 670-95-1 4-Phenylimidazole 
• 88333-03-3 Benzyl isocyanide 

Downstream Products

• 104749-69-1 4-Phenyl-1-(phenylmethyl)-1H-imidazole-2-carbonitrile 
• 1341165-20-5 1-benzyl-3-methyl-4-phenyl-1,3-dihydro-2H-imidazol-2-one 
• 1341165-00-1 1-benzyl-3-methyl-4-phenyl-1H-imidazol-3-ium iodide 
• 61001-00-1 2-phenyl-5H-imidazo<2,1-a>isoindole 
• 1026982-44-4 [2-(1-Benzyl-4-phenyl-1H-imidazol-2-ylsulfanylmethyl)-phenyl]-dimethyl-amine 

Relevant academic research and scientific papers

Structure-guided optimization of 1H-imidazole-2-carboxylic acid derivatives affording potent VIM-Type metallo-β-lactamase inhibitors

Production of metallo-β-lactamases (MBLs) in bacterial pathogens is an important cause of resistance to the ‘last-resort’ carbapenem antibiotics. Development of effective MBL inhibitors to reverse carbapenem resistance in Gram-negative bacteria is still needed. We herein report X-ray structure-guided optimization of 1H-imidazole-2-carboxylic acid (ICA) derivatives by considering how to engage with the active-site flexible loops and improve penetration into Gram-negative bacteria. Structure-activity relationship studies revealed the importance of appropriate substituents at ICA 1-position to achieve potent inhibition to class B1 MBLs, particularly the Verona Integron-encoded MBLs (VIMs), mainly by involving ingenious interactions with the flexible active site loops as observed by crystallographic analyses. Of the tested ICA inhibitors, 55 displayed potent synergistic antibacterial activity with meropenem against engineered Escherichia coli strains and even intractable clinically isolated Pseudomonas aeruginosa producing VIM-2 MBL. The morphologic and internal structural changes of bacterial cells after treatment further demonstrated that 55 crossed the outer membrane and reversed the activity of meropenem. Moreover, 55 showed good pharmacokinetic and safety profile in vivo, which could be a potential candidate for combating VIM-mediated Gram-negative carbapenem resistance.

Tandem insertion-cyclization reaction of isocyanides in the synthesis of 1,4-diaryl-1H-imidazoles: Presence of N-arylformimidate intermediate

A straightforward and high-yielding synthesis of 1,4-diaryl-1H-imidazoles is reported. 1,4-Diaryl-1H-imidazoles have been difficult to access in ambient conditions, but our method utilizes two different facets of isocyanide reactivity to achieve it. The r

C-H bonds as ubiquitous functionality: A general approach to complex arylated imidazoles via regioselective sequential arylation of all three C-H bonds and regioselective n -alkylation enabled by SEM-group transposition

(Figure presented) Imidazoles are an important group of the azole family of heterocycles frequently found in pharmaceuticals, drug candidates, ligands for transition metal catalysts, and other molecular functional materials. Owing to their wide application in academia and industry, new methods and strategies for the generation of functionalized imidazole derivatives are in demand. We here describe a general and comprehensive approach for the synthesis of complex aryl imidazoles, where all three C-H bonds of the imidazole core can be arylated in a regioselective and sequential manner. We report new catalytic methods for selective C5- and C2-arylation of SEM-imidazoles and provide a mechanistic hypothesis for the observed positional selectivity based on electronic properties of C-H bonds and the heterocyclic ring. Importantly, aryl bromides and low-cost aryl chlorides can be used as arene donors under practical laboratory conditions. To circumvent the low reactivity of the C-4 position, we developed the SEM-switch that transfers the SEM-group from N-1 to N-3 nitrogen and thus enables preparation of 4-arylimidazoles and sequential C4-C5-arylation of the imidazole core. Furthermore, selective N3-alkylation followed by the SEM-group deprotection (trans-N-alkylation) allows for regioselective N-alkylation of complex imidazoles. The sequential C-arylation enabled by the SEM-switch allowed us to produce a variety of mono-, di-, and triarylimidazoles using diverse bromo- and chloroarenes. Using our approach, the synthesis of individual compounds or libraries of analogues can begin from either the parent imidazole or a substituted imidazole, providing rapid access to complex imidazole structures.

Structure based development of phenylimidazole-derived inhibitors of indoleamine 2,3-dioxygenase

Indoleamine 2,3-dioxygenase (IDO) is emerging as an important new therapeutic target for the treatment of cancer, chronic viral infections, and other diseases characterized by pathological immune suppression. With the goal of developing more potent IDO in

Unexpected reactivity of imidazo[2,1-b]thiazolines with organometallic reagents

The reaction of imidazo[2,1-b]thiazolines with various organometallic reagents is described. Nucleophilic attack of organolithium reagents on sulfur occurs with extrusion of ethylene to produce 2-thioalkyl-or 2-thioarylimidazoles. The outcome with Grignar