745053-46-7

Basic information

• Product Name: (R)-2-(4-methanesulfonylphenyl)-3-(tetrahydropyran-4-yl)propionic acid
• Synonyms: (R)-2-(4-methanesulfonylphenyl)-3-(tetrahydropyran-4-yl)propionic acid
• CAS NO: 745053-46-7
• Molecular Weight: 312.387
• Mol File: 745053-46-7.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (R)-2-(4-methanesulfonylphenyl)-3-(tetrahydropyran-4-yl)propionic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-(4-methanesulfonylphenyl)-3-(tetrahydropyran-4-yl)propionic acid(745053-46-7)
• EPA Substance Registry System: (R)-2-(4-methanesulfonylphenyl)-3-(tetrahydropyran-4-yl)propionic acid(745053-46-7)

Safety Data

• Hazardous Substances Data: 745053-46-7(Hazardous Substances Data)

Upstream product

• 745053-47-8 (4R)-4-benzyl-3-[(2R)-2-[4-(methylsulfonyl)phenyl]-3-(tetrahydro-2H-pyran-4-yl)propanoyl]-1,3-oxazolidin-2-one 
• 745053-01-4 (E)-2-(4-(methylsulfonyl)phenyl)-3-(tetrahydro-2H-pyran-4-yl)acrylic acid 

Downstream Products

• 745051-60-9 (2R)-3-(tetrahydropyran-4-yl)-2-(4-methanesulfonylphenyl)-N-thiazol-2-ylpropionamide 

Relevant articles and documents

Design, synthesis, and pharmacological evaluation of N-(4-mono and 4,5-disubstituted thiazol-2-yl)-2-aryl-3-(tetrahydro-2H-pyran-4-yl)propanamides as glucokinase activators

A series of N-thiazole substituted arylacetamides were designed on the basis of metabolic mechanism of the aminothiazole fragment as glucokinase (GK) activators for the treatment of type 2 diabetes. Instead of introducing a substituent to block the metabolic sensitive C-5 position on the thiazole core directly, a wide variety of C-4 or both C-4 and C-5 substitutions were explored. Compound R-9k bearing an iso-propyl group as the C-4 substituent was found possessing the highest GK activation potency with an EC50 of 0.026 μM. This compound significantly increased both glucose uptake and glycogen synthesis in rat primary cultured hepatocytes. Moreover, single oral administration of compound R-9k exerted significant reduction of blood glucose levels in both ICR and ob/ob mice. These promising results indicated that compound R-9k is a potent orally active GK activator, and is warranted for further investigation as a new anti-diabetic treatment.

SAR, pharmacokinetics, safety, and efficacy of glucokinase activating 2-(4-sulfonylphenyl)-N-thiazol-2-ylacetamides: Discovery of PSN-GK1

Allosteric activators of the glucose-sensing enzyme glucokinase (GK) are currently attracting much interest as potential antidiabetic therapies because they can achieve powerful blood glucose lowering through actions in multiple organs. Here, the optimization of a weakly active high-throughput screening hit to (2R)-2-(4-cyclopropanesulfonylphenyl)-N-(5-fluorothiazol-2-yl)-3- (tetrahydropyran-4-yl)propionamide (PSN-GK1), a potent GK activator with an improved pharmacokinetic and safety profile, is described. Following oral administration, this compound elicited robust glucose lowering in rats.