1219741-71-5

Basic information

• Product Name: methyl 5-[(6-chloro-5-(1-methyl-1H-indol-5-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazol-2-yl)oxy]-2-methylbenzoate
• Synonyms: methyl 5-[(6-chloro-5-(1-methyl-1H-indol-5-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazol-2-yl)oxy]-2-methylbenzoate
• CAS NO: 1219741-71-5
• Molecular Weight: 576.167
• Mol File: 1219741-71-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: methyl 5-[(6-chloro-5-(1-methyl-1H-indol-5-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazol-2-yl)oxy]-2-methylbenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 5-[(6-chloro-5-(1-methyl-1H-indol-5-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazol-2-yl)oxy]-2-methylbenzoate(1219741-71-5)
• EPA Substance Registry System: methyl 5-[(6-chloro-5-(1-methyl-1H-indol-5-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazol-2-yl)oxy]-2-methylbenzoate(1219741-71-5)

Safety Data

• Hazardous Substances Data: 1219741-71-5(Hazardous Substances Data)

Upstream product

• 1219741-22-6 6-chloro-5-iodo-2-(methylthio)-1H-benzimidazole 
• 1219741-24-8 6-chloro-5-iodo-2-(methylsulfonyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole 
• 1219741-20-4 2, 4-chloro-5-iodobenzene-1,2-diamine 
• 335349-57-0 2-nitro-4-iodo-5-chloroaniline 
• 837392-62-8 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole 
• 1219741-39-5 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.