1219741-39-5

Basic information

• Product Name: methyl 5-[(6-chloro-5-iodo-1-{[2-(trimethylsilyl)ethoxy]-methyl}-1H-benzimidazol-2-yl)oxy]-2-methylbenzoate
• Synonyms: methyl 5-[(6-chloro-5-iodo-1-{[2-(trimethylsilyl)ethoxy]-methyl}-1H-benzimidazol-2-yl)oxy]-2-methylbenzoate
• CAS NO: 1219741-39-5
• Molecular Weight: 572.902
• Mol File: 1219741-39-5.mol

Chemical Properties

• CAS DataBase Reference: methyl 5-[(6-chloro-5-iodo-1-{[2-(trimethylsilyl)ethoxy]-methyl}-1H-benzimidazol-2-yl)oxy]-2-methylbenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 5-[(6-chloro-5-iodo-1-{[2-(trimethylsilyl)ethoxy]-methyl}-1H-benzimidazol-2-yl)oxy]-2-methylbenzoate(1219741-39-5)
• EPA Substance Registry System: methyl 5-[(6-chloro-5-iodo-1-{[2-(trimethylsilyl)ethoxy]-methyl}-1H-benzimidazol-2-yl)oxy]-2-methylbenzoate(1219741-39-5)

Safety Data

• Hazardous Substances Data: 1219741-39-5(Hazardous Substances Data)

Upstream product

• 1219741-22-6 6-chloro-5-iodo-2-(methylthio)-1H-benzimidazole 
• 1219741-19-1 6-chloro-5-iodo-2-(methylsulfonyl)-1H-benzo[d]imidazole 
• 1219741-20-4 2, 4-chloro-5-iodobenzene-1,2-diamine 
• 335349-57-0 2-nitro-4-iodo-5-chloroaniline 
• 1635-61-6 5-chloro-2-nitroaniline 
• 1219741-24-8 6-chloro-5-iodo-2-(methylsulfonyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole 
• 73505-48-3 methyl 3-hydroxy-6-methylbenzoate 

Downstream Products

• 1219741-42-0 methyl 5-[(6-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazol-2-yl)oxy]-2-methylbenzoate 
• 1219741-71-5 methyl 5-[(6-chloro-5-(1-methyl-1H-indol-5-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazol-2-yl)oxy]-2-methylbenzoate 
• 1219739-36-2 5-((6-chloro-5-(1-methyl-1H-indol-5-yl)-1H-benzo[d]-imidazol-2-yl)oxy)-2-methylbenzoic acid 
• 1219741-74-8 5-[(6-chloro-5-(4-pyrrolidin-1-ylphenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazol-2-yl)oxy]-2-methylbenzoic acid 
• 1219741-41-9 methyl 5-[(6-chloro-5-iodo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazol-2-yl)oxy]-2-methylbenzoate 

Relevant articles and documents

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.

NOVEL CYCLIC BENZIMIDAZOLE DERIVATIVES USEFUL 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