865137-76-4

Basic information

• Product Name: 2-Propenoic acid, 3-(4-amino-2-fluorophenyl)-, ethyl ester, (2E)-
• CAS NO: 865137-76-4
• Molecular Formula: C11H12FNO2
• Molecular Weight: 209.22
• Mol File: 865137-76-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2-Propenoic acid, 3-(4-amino-2-fluorophenyl)-, ethyl ester, (2E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenoic acid, 3-(4-amino-2-fluorophenyl)-, ethyl ester, (2E)-(865137-76-4)
• EPA Substance Registry System: 2-Propenoic acid, 3-(4-amino-2-fluorophenyl)-, ethyl ester, (2E)-(865137-76-4)

Safety Data

• Hazardous Substances Data: 865137-76-4(Hazardous Substances Data)

Upstream product

• 656-65-5 3-fluoro-4-bromophenylamine 
• 140-88-5 ethyl acrylate 

Downstream Products

• 1390641-92-5 (E)-3-(2-fluoro-4-(((2'-methyl-[1,1'-biphenyl]-3-yl)methyl)amino)phenyl)acrylic acid 
• 1373223-15-4 3-(4-amino-2-fluorophenyl)propanoic acid 
• 1390641-83-4 (E)-3-(4-amino-2-fluorophenyl)acrylic Acid 
• 1390641-90-3 3-(2-fluoro-4-(((2-methyl-4-(3-(methylsulfonyl)propoxy)-[1,1'-biphenyl]-3'-yl)methyl)amino)phenyl)propanoic acid 
• 1390641-89-0 3-(4-(((2',6'-dimethyl-[1,1'-biphenyl]-3-yl)methyl)amino)-2-fluorophenyl)propanoic acid 
• 1390641-88-9 3-(4-(((2'-ethyl-[1,1'-biphenyl]-3-yl)methyl)amino)-2-fluorophenyl)propanoic acid 
• 1390641-87-8 3-(2-fluoro-4-(((2'-methyl-[1,1'-biphenyl]-3-yl)methyl)amino)phenyl)propanoic acid 
• 865134-67-4 3-[4-({[4'-(2-ethoxyethoxy)-2',6'-dimethylbiphenyl-3-yl]methyl}amino)-2-fluorophenyl]propanoic acid 
• 865137-78-6 ethyl 3-(2-fluoro-4-{[(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate 
• 865136-34-1 3-{2-fluoro-4-[({4'-[(4-hydroxy-1,1-dioxidotetrahydro-2H-thiopyran-4-yl)methoxy]-2',6'-dimethylbiphenyl-3-yl}methyl)amino]phenyl}propanoic acid 

Relevant articles and documents

Discovery of phenylpropanoic acid derivatives containing polar functionalities as potent and orally bioavailable G protein-coupled receptor 40 agonists for the treatment of type 2 diabetes

As part of a program to identify potent GPR40 agonists with drug-like properties suitable for clinical development, the incorporation of polar substituents was explored with the intention of decreasing the lipophilicity of our recently disclosed phenylpropanoic acid derivative 1. This incorporation would allow us to mitigate the cytotoxicity issues observed with compound 1 and enable us to move away from the multifunctional free fatty acid-like structure. Substitutions on the 2′,6′-dimethylbiphenyl ring were initially undertaken, which revealed the feasibility of introducing polar functionalities at the biphenyl 4′-position. Further optimization of this position and the linker led to the discovery of several 4′-alkoxybiphenyl derivatives, which showed potent GPR40 agonist activities with the best balance in terms of improved cytotoxicity profiles and favorable pharmacokinetic properties. Among them, 3-{2-fluoro-4-[({4′-[(4-hydroxy-1,1-dioxidotetrahydro-2H-thiopyran- 4-yl)methoxy]-2′,6′-dimethylbiphenyl-3-yl}methyl)amino]phenyl} propanoic acid (35) exhibited a robust plasma glucose-lowering effect and insulinotropic action during an oral glucose tolerance test in rats with impaired glucose tolerance.

CYCLOPROPANECARBOXYLIC ACID COMPOUND

A compound of the formula (I): wherein each symbol is as defined in the description, a salt thereof, and a prodrug thereof of the present invention unexpectedly have a superior GPR40 receptor agonist activity and superior properties as pharmaceutical prod