1219737-12-8

Basic information

• Product Name: 5-((5-([1,1'-biphenyl]-4-yl)-6-chloro-1H-benzo[d]imidazol-2-yl)oxy)-2-methylbenzoic acid
• Synonyms: 5-((5-([1,1'-biphenyl]-4-yl)-6-chloro-1H-benzo[d]imidazol-2-yl)oxy)-2-methylbenzoic acid
• CAS NO: 1219737-12-8
• Molecular Weight: 454.912
• Mol File: 1219737-12-8.mol

Chemical Properties

• Boiling Point: 712.6±70.0 °C(Predicted)
• Density: 1.349±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 5-((5-([1,1'-biphenyl]-4-yl)-6-chloro-1H-benzo[d]imidazol-2-yl)oxy)-2-methylbenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-((5-([1,1'-biphenyl]-4-yl)-6-chloro-1H-benzo[d]imidazol-2-yl)oxy)-2-methylbenzoic acid(1219737-12-8)
• EPA Substance Registry System: 5-((5-([1,1'-biphenyl]-4-yl)-6-chloro-1H-benzo[d]imidazol-2-yl)oxy)-2-methylbenzoic acid(1219737-12-8)

Safety Data

• Hazardous Substances Data: 1219737-12-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-((5-([1,1'-biphenyl]-4-yl)-6-chloro-1H-benzo[d]imidazol-2-yl)oxy)-2-methylbenzoic acid is used as a potential therapeutic agent for the activation of AMP-activated protein kinase (AMPK). Its activation of AMPK, with an EC50 of 8 nM, suggests that it may play a role in modulating cellular energy homeostasis and could be useful in the development of treatments for metabolic disorders and other conditions related to AMPK dysregulation.
Used in Chemical Research:
In the field of chemical research, 5-((5-([1,1'-biphenyl]-4-yl)-6-chloro-1H-benzo[d]imidazol-2-yl)oxy)-2-methylbenzoic acid may serve as a starting material or intermediate for the synthesis of more complex molecules with specific biological activities. Its unique structure could be exploited to design new drugs or materials with tailored properties.

Upstream product

• 1635-61-6 5-chloro-2-nitroaniline 
• 335349-57-0 2-nitro-4-iodo-5-chloroaniline 
• 1219741-20-4 2, 4-chloro-5-iodobenzene-1,2-diamine 
• 1219741-21-5 3,5-chloro-6-iodo-1,3-dihydro-2H-benzimidazole-2-thione 
• 1219741-19-1 6-chloro-5-iodo-2-(methylsulfonyl)-1H-benzo[d]imidazole 
• 1219741-22-6 6-chloro-5-iodo-2-(methylthio)-1H-benzimidazole 
• 1219741-56-6 5-biphenyl-4-yl-6-chloro-2-(methylsulfonyl)-1H-benzimidazole 
• 1219741-21-5 5-chloro-6-iodo-2,3-dihydro-1H-1,3-benzodiazole-2-thione 
• 1219741-57-7 methyl 5-[(5-biphenyl-4-yl-6-chloro-1H-benzimidazol-2-yl)oxy]-2-methylbenzoate 

Relevant articles and documents

Discovery of MK-8722: A Systemic, Direct Pan-Activator of AMP-Activated Protein Kinase

5′-Adenosine monophosphate-activated protein kinase (AMPK) is a key regulator of mammalian energy homeostasis and has been implicated in mediating many of the beneficial effects of exercise and weight loss including lipid and glucose trafficking. As such,

Hit-to-Lead Optimization and Discovery of 5-((5-([1,1′-Biphenyl]-4-yl)-6-chloro-1H-benzo[d]imidazol-2-yl)oxy)-2-methylbenzoic Acid (MK-3903): A Novel Class of Benzimidazole-Based Activators of AMP-Activated Protein Kinase

AMP-activated protein kinase (AMPK) plays an essential role as a cellular energy sensor and master regulator of metabolism in eukaryotes. Dysregulated lipid and carbohydrate metabolism resulting from insulin resistance leads to hyperglycemia, the hallmark of type 2 diabetes mellitus (T2DM). While pharmacological activation of AMPK is anticipated to improve these parameters, the discovery of selective, direct activators has proven challenging. We now describe a hit-to-lead effort resulting in the discovery of a potent and selective class of benzimidazole-based direct AMPK activators, exemplified by 5-((5-([1,1′-biphenyl]-4-yl)-6-chloro-1H-benzo[d]imidazol-2-yl)oxy)-2-methylbenzoic acid, 42 (MK-3903). Compound 42 exhibited robust target engagement in mouse liver following oral dosing, leading to improved lipid metabolism and insulin sensitization in mice.

NOVEL CYCLIC BENZIMIDAZOLE DERIVATIVES USEFUL AS ANTI-DIABETIC AGENTS

Novel compounds of the structural formula (I) are activators of AMP-protein kinase and are useful in the treatment, prevention and suppression of diseases mediated by the AMPK-activated protein kinase. The compounds of the present invention are useful in the treatment of Type 2 diabetes, hyperglycemia, metabolic syndrome, obesity, hypercholesterolemia, and hypertension.