1235567-13-1

Basic information

• Product Name: Methyl 3-(4-Methanesulfonylphenoxy)-5-(tetraMethyl- 1,3,2-dioxaborolan-2-yl)benzoate
• Synonyms: Methyl 3-(4-Methanesulfonylphenoxy)-5-(tetraMethyl- 1,3,2-dioxaborolan-2-yl)benzoate;3-[4-(methylsulfonyl)phenoxy]-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid methyl ester
• CAS NO: 1235567-13-1
• Molecular Formula: C₂₁H₂₅BO₇S
• Molecular Weight: 432.295
• Mol File: 1235567-13-1.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Methyl 3-(4-Methanesulfonylphenoxy)-5-(tetraMethyl- 1,3,2-dioxaborolan-2-yl)benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 3-(4-Methanesulfonylphenoxy)-5-(tetraMethyl- 1,3,2-dioxaborolan-2-yl)benzoate(1235567-13-1)
• EPA Substance Registry System: Methyl 3-(4-Methanesulfonylphenoxy)-5-(tetraMethyl- 1,3,2-dioxaborolan-2-yl)benzoate(1235567-13-1)

Safety Data

• Hazardous Substances Data: 1235567-13-1(Hazardous Substances Data)

Upstream product

• 1235567-12-0 3-(4-methanesulfonylphenoxy)-5-trifluoromethanesulfonyloxybenzoic acid methyl ester 
• 73183-34-3 bis(pinacol)diborane 
• 752242-45-8 3-hydroxy-5-(4-methanesulfonylphenoxy)benzoic acid methyl ester 
• 2150-44-9 1-carbomethoxy-3,5-dihydroxybenzene 

Downstream Products

• 1596340-68-9 3-(4-methanesulfonylphenoxy)-5-(3-methylpyridin-2-yl)benzoic acid 
• 1596340-69-0 {2-[3-(4-methanesulfonylphenoxy)-5-(3-methylpyridine-2-yl)benzoylamino]thiazol-4-yl}acetic acid 
• 1596340-70-3 N-(4-cyclopropylcarbamoylmethylthiazol-2-yl)-3-(4-methanesulfonylphenoxy)-5-(3-methylpyridine-2-yl)benzamide 
• 1596340-72-5 3-(4-methanesulfonylphenoxy)-5-(3-methylpyridin-2-yl)-N-thiazol-2-yl-benzamide 
• 1596340-73-6 N-(5-fluorothiazol-2-yl)-3-(4-methanesulfonylphenoxy)-5-(3-methylpyridin-2-yl)benzamide 
• 1596340-92-9 3-(4-methanesulfonylphenoxy)-5-(3-methylpyridin-2-yl)benzoyl chloride 
• 1596340-74-7 N-(4-chloromethylthiazol-2-yl)-3-(4-methanesulfonylphenoxy)-5-(3-methylpyridine-2-yl)benzamide 
• 1596340-75-8 N-(4-diethylaminomethylthiazol-2-yl)-3-(4-methanesulfonylphenoxy)-5-(3-methylpyridin-2-yl)benzamide 
• 1596340-76-9 3-(4-methanesulfonylphenoxy)-5-(3-methylpyridin-2-yl)-N-(4-morpholin-4-ylmethylthiazol-2-yl)benzamide 
• 1596340-77-0 3-(4-methanesulfonylphenoxy)-N-[4-(4-methylpiperazin-1-ylmethyl)thiazol-2-yl]-5-(3-methylpyridin-2-yl)benzamide 
• 1596340-78-1 N-(4-{[bis(2-methoxyethyl)amino]methyl}thiazol-2-yl)-3-(4-methanesulfonylphenoxy)-5-(3-methylpyridin-2-yl)benzamide 
• 1596340-79-2 3-(4-methanesulfonylphenoxy)-N-(4-{[(2-methoxyethyl)methylamino]methyl}thiazol-2-yl)-5-(3-methylpyridin-2-yl)benzamide 
• 1596340-80-5 3-(4-methanesulfonylphenoxy)-5-(3-methylpyridin-2-yl)-N-(4-piperazin-1-ylmethylthiazol-2-yl)benzamide 
• 1596340-81-6 3-(4-methanesulfonylphenoxy)-N-{4-[(2-methoxy-1-methylethylamino)methyl]thiazol-2-yl}-5-(3-methylpyridin-2-yl)benzamide 

Relevant articles and documents

Discovery of 3-(4-methanesulfonylphenoxy)-N-[1-(2-methoxy-ethoxymethyl)-1H- pyrazol-3-yl]-5-(3-methylpyridin-2-yl)-benzamide as a novel glucokinase activator (GKA) for the treatment of type 2 diabetes mellitus

Novel heteroaryl-containing benzamide derivatives were synthesized and screened using an in vitro assay measuring increases in glucose uptake and glucokinase activity stimulated by 10 mM glucose in rat hepatocytes. From a library of synthesized compounds, 3-(4-methanesulfonylphenoxy)-N-[1-(2-methoxy- ethoxymethyl)-1H-pyrazol-3-yl]-5-(3-methyl pyridin-2-yl)-benzamide (19e) was identified as a potent glucokinase activator with assays demonstrating an EC50 of 315 nM and the induction of a 2.23 fold increase in glucose uptake. Compound 19e exhibited a glucose AUC reduction of 32% (50 mg/kg) in an OGTT study with C57BL/6J mice compared to 28% for metformin (300 mg/kg). Single treatment of the compound in C57BL/J6 and ob/ob mice elicited basal glucose lowering activity, while in a two-week repeated dose study with ob/ob mice, the compound significantly decreased blood glucose levels with no evidence of hypoglycemia risk. In addition, 19e exhibited favorable pharmacokinetic parameters in mice and rats and excellent safety margins in liver and testicular toxicity studies. Compound 19e was therefore selected as a development candidate for the potential treatment of type 2 diabetes.