865137-77-5

Basic information

• Product Name: ethyl 3-(4-amino-2-fluorophenyl)propanoate
• Synonyms: ethyl 3-(4-amino-2-fluorophenyl)propanoate;3-(4-Amino-2-fluoro-phenyl)-propionic acid ethyl ester
• CAS NO: 865137-77-5
• Molecular Formula: C₁₁H₁₄FNO₂
• Molecular Weight: 211.2327632
• Mol File: 865137-77-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: ethyl 3-(4-amino-2-fluorophenyl)propanoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 3-(4-amino-2-fluorophenyl)propanoate(865137-77-5)
• EPA Substance Registry System: ethyl 3-(4-amino-2-fluorophenyl)propanoate(865137-77-5)

Safety Data

• Hazardous Substances Data: 865137-77-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Development:
Ethyl 3-(4-amino-2-fluorophenyl)propanoate is utilized as a key intermediate in the synthesis of various pharmaceutical drugs. Its unique structure, including the fluorine atom and the ethyl ester group, contributes to its potential as a building block for creating novel therapeutic agents.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, ethyl 3-(4-amino-2-fluorophenyl)propanoate serves as a valuable compound for research purposes. Its structural features allow scientists to explore its interactions with biological targets, potentially leading to the discovery of new drugs with improved efficacy and selectivity.
Used in Drug Design and Optimization:
Ethyl 3-(4-amino-2-fluorophenyl)propanoate is employed as a starting material in drug design and optimization processes. Its chemical properties can be modified to enhance the pharmacokinetic and pharmacodynamic profiles of drug candidates, aiming to develop safer and more effective medications.
Used in Biochemical and Enzymatic Studies:
ethyl 3-(4-amino-2-fluorophenyl)propanoate can be used in biochemical and enzymatic studies to investigate the mechanisms of action of enzymes and other proteins involved in various biological processes. Understanding these interactions can provide insights into the development of targeted therapies for specific diseases.
Used in Chemical Synthesis:
Ethyl 3-(4-amino-2-fluorophenyl)propanoate is also used in chemical synthesis for the preparation of other organic compounds and materials. Its versatility in chemical reactions makes it a valuable component in the synthesis of specialty chemicals and advanced materials for various applications.

Upstream product

• 865137-76-4 ethyl (2E)-3-(4-amino-2-fluorophenyl)prop-2-enoate 
• 656-65-5 3-fluoro-4-bromophenylamine 
• 140-88-5 ethyl acrylate 

Downstream Products

• 865137-78-6 ethyl 3-(2-fluoro-4-{[(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate 
• 865136-32-9 ethyl 3-(2-fluoro-4-{({4'-[(4-hydroxy-1,1-dioxidotetrahydro-2H-thiopyran-4-yl)methoxy]-2',6'-dimethylbiphenyl-3-yl}methyl)[(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate 
• 865136-33-0 ethyl 3-{2-fluoro-4-[({4'-[(4-hydroxy-1,1-dioxidotetrahydro-2H-thiopyran-4-yl)methoxy]-2',6'-dimethylbiphenyl-3-yl}methyl)amino]phenyl}propanoate 
• 865136-31-8 ethyl 3-(2-fluoro-4-{({4'-[(4-hydroxytetrahydro-2H-thiopyran-4-yl)methoxy]-2',6'-dimethylbiphenyl-3-yl}methyl)[(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 
• 865134-67-4 3-[4-({[4'-(2-ethoxyethoxy)-2',6'-dimethylbiphenyl-3-yl]methyl}amino)-2-fluorophenyl]propanoic acid 
• 1030849-42-3 ethyl 3-[2-fluoro-4-({[8-(4-fluorophenyl)-5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl]methyl}amino)phenyl]propanoate 
• 1030849-25-2 tert-butyl 7-({[4-(3-ethoxy-3-oxopropyl)-3-fluorophenyl]amino}methyl)-8-methyl-3,4-dihydroquinoline-1(2H)-carboxylate 

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.

AMINOPHENYLPROPANOIC ACID DERIVATIVE

A compound represented by the formula (1): wherein each symbol is as defined in the specification, and a salt thereof and a prodrug thereof unexpectedly have superior GPR40 receptor agonist activity, superior in the properties as a pharmaceutical product such as stability and the like, and can be a safe and useful pharmaceutical agent as a drug for the prophylaxis or treatment of GPR40 receptor related pathology or diseases such as diabetes and the like.