2411-77-0

Usage

Type of compound

Chemical compound, derivative of imidazole

Common uses

Biochemical and pharmaceutical research

Potential applications

Ligand in metal complexes, precursor in organic synthesis, building block for pharmaceutical compounds

Therapeutic potential

Neuroprotective properties, studied for treatment of neurological disorders such as Parkinson's disease

Physical properties

White crystalline solid at room temperature

Solubility

Soluble in organic solvents such as ethanol and diethyl ether

Upstream product

• 93782-03-7 1-methyl-4-phenyl-1,3-dihydro-imidazol-2-one 
• 25433-14-1 1-methyl-4-phenyl-1,3-dihydroimidazole-2-thione 
• 41217-55-4 1,3-dimethyl-4-phenyl-1H-imidazol-2-ium iodide 
• 670-95-1 4-Phenylimidazole 
• 74-88-4 methyl iodide 
• 38036-86-1 N-acetyl-4⁽⁵⁾-phenylimidazole 
• 10199-69-6 1-methyl-4-phenyl-1H-pyrazole 
• 3463-27-2 1-methyl-5-phenyl-1H-pyrazole 
• 25676-75-9 4-bromo-1-methyl-1H-imidazole 
• 5123-13-7 5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane 
• 591-51-5 phenyllithium 
• 71759-87-0 4-iodo-1-methyl-1H-imidazole 
• 670-95-1 4-phenyl-1H-imidazole 
• 70-11-1 α-bromoacetophenone 

Downstream Products

• 41217-55-4 1,3-dimethyl-4-phenyl-1H-imidazol-2-ium iodide 
• 141264-27-9 N'-benzoyl-N-methyl-N-formylurea 
• 196810-82-9 2-(1-methyl-4-phenyl-1H-imidazol-2-yl)ethanol 
• 123511-51-3 1-methyl-4-phenyl-1H-imidazole-2-carbaldehyde 
• 948564-15-6 2-chloro-1-methyl-4-phenyl-1H-imidazole 
• 1083051-76-6 4-hydroxy-4-(1-methyl-4-phenyl-1H-imidazol-2-yl)-piperidine-1-carboxylic acid tert-butyl ester 
• 1438258-15-1 2-(2-(1-methyl-4-phenyl-1H-imidazol-2-yl)ethyl)-5-morpholino-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one 
• 1438258-14-0 5-bromo-2-(2-(1-methyl-4-phenyl-1H-imidazol-2-yl)ethyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one 
• 1429781-97-4 2-methyl-4-(1-methyl-4-phenyl-1H-imidazol-2-yl)-but-3-yn-2-ol 
• 1429781-96-3 2-iodo-1-methyl-4-phenyl-1H-imidazole 
• 1429781-98-5 2-ethynyl-1-methyl-4-phenyl-1H-imidazole 
• 1429781-54-3 2-methyl-4-[2-(1-methyl-4-phenyl-1H-imidazol-2-yl)-ethyl]-pyrido[2,3-d]pyrimidine 
• 1429781-12-3 2-methyl-4-(1-methyl-4-phenyl-1H-imidazol-2-ylethynyl)-pyrido[2,3-d]pyrimidine 
• 1429780-95-9 5-fluoro-4-methyl-2-(1-methyl-4-phenyl-1H-imidazol-2-ylethynyl)-quinazoline 

Relevant academic research and scientific papers

3-(AZOLYLMETHOXY)BIPHENYL DERIVATIVES AS INHIBITORS OF THE PD-1/PD-L1 PROTEIN/PROTEIN INTERACTION

The present invention provides novel compounds of formula (I) that are useful as inhibitors of the PD-1/PD-L1 protein/protein interaction. The compounds may be used in the treatment of cancer, infectious diseases and neurodegenerative diseases such as schizophrenia, Alzheimer, multiple sclerosis or Parkinson.

Cobalt-Catalyzed Cross-Coupling Reactions of Arylboronic Esters and Aryl Halides

An efficient cobalt catalyst system for the Suzuki-Miyaura cross-coupling reaction of arylboronic esters and aryl halides has been identified. In the presence of cobalt(II)/terpyridine catalyst and potassium methoxide, a diverse array of (hetero)biaryls have been prepared in moderate to excellent yields.

Design, Synthesis, and Application of Polymer-Supported Silicon-Transfer Agents for Cross-Coupling Reactions with Organolithium Reagents

The initial design, synthesis, and validation of polymer-supported siloxane transfer agents have been achieved that permit the direct use of organolithium reagents in the palladium-catalyzed cross-coupling reactions. Through rational design, two generations of polymer support were developed that significantly simplify product purification and the transfer agent recycling.

QUINAZOLINE DERIVATIVES AS PDE10A ENZYME INHIBITORS

This invention is directed to compounds, which are PDE10A enzyme inhibitors. The invention provides a pharmaceutical composition comprising a therapeutically effective amount of a compound of the invention and a pharmaceutically acceptable carrier. The pr

TRIAZOLOPYRIDINONE PDE10 INHIBITORS

The present invention is directed to triazolopyridinone compounds which are useful as therapeutic agents for the treatment of central nervous system disorders associated with phosphodiesterase 10 (PDE10). The present invention also relates to the use of such compounds for treating neurological and psychiatric disorders, such as schizophrenia, psychosis or Huntington's disease, and those associated with striatal hypofunction or basal ganglia dysfunction.

Novel series of 3-amino-N-(4-aryl-1,1-dioxothian-4-yl)butanamides as potent and selective dipeptidyl peptidase IV inhibitors

A series of novel 3-amino-N-(4-aryl-1,1-dioxothian-4-yl)butanamides were investigated as dipeptidyl peptidase IV (DPP-4) inhibitors. Introduction of a 4-phenylthiazol-2-yl group showed highly potent DPP-4 inhibitory activity. Among various derivatives, (3R)-3-amino-N-(4-(4-phenylthiazol-2-yl)-tetrahydro-2H- thiopyran-4-yl)-4-(2,4,5-trifluorophenyl)butanamide 1,1-dioxide (30) reduced blood glucose excursion in an oral glucose tolerance test by oral administration.

HETEROARYL COMPOUNDS AND METHODS OF USE THEREOF

Provided herein are heteroaryl compounds, methods of their synthesis, pharmaceutical compositions comprising the compounds, and methods of their use. In one embodiment, the compounds provided herein are useful for the treatment, prevention, and/or management of various disorders, such as CNS disorders and metabolic disorders, including, but not limited to, e.g., neurological disorders, psychosis, schizophrenia, obesity, and diabetes

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.

Discovery and optimization of substituted 1-(1-phenyl-1H-pyrazol-3-yl) methanamines as potent and efficacious type II calcimimetics

Our efforts to discover potent, orally bioavailable type II calcimimetic agents for the treatment of secondary hyperparathyroidism focused on the development of ring constrained analogues of the known calcimimetic R-568. The structure-activity relationships of various substituted heterocycles and their effects on the human calcium-sensing receptor are discussed. Pyrazole 15 was shown to be efficacious in a rat in vivo pharmacodynamic model.

CALCIUM RECEPTOR MODULATING AGENTS

The present invention relates generally to novel calcimimetic compounds and pharmaceutical compositions comprising them. The invention also relates to methods of treating of diseases or disorders related to the function of the calcium sensing receptor using the compounds represented in Formula I.