117391-51-2

Usage

Uses

Used in Organic Synthesis:
3-Amino-3-(3-fluorophenyl)propanoic acid is used as a research intermediate for organic synthesis, particularly in the development of new pharmaceuticals and chemical compounds. Its unique structure allows for further functionalization and modification, making it a valuable building block in the creation of more complex molecules with specific biological activities.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-Amino-3-(3-fluorophenyl)propanoic acid is used as a key intermediate in the synthesis of various drugs. Its fluorinated aromatic ring and amino acid-like structure contribute to its potential as a starting material for designing new therapeutic agents with improved pharmacological properties.
Used in Chemical Research:
3-Amino-3-(3-fluorophenyl)propanoic acid is also utilized in chemical research for studying reaction mechanisms, exploring new synthetic routes, and understanding the effects of structural modifications on the reactivity and properties of molecules. This knowledge can be applied to optimize existing synthetic processes and develop novel chemical methodologies.

InChI:InChI=1/C9H10FNO2/c10-7-3-1-2-6(4-7)8(11)5-9(12)13/h1-4,8H,5,11H2,(H,12,13)

Upstream product

• 141-82-2 malonic acid 
• 456-48-4 3-Fluorobenzaldehyde 

Downstream Products

• 117291-14-2 3-(3-Fluoro-phenyl)-3-(2,2,2-trifluoro-acetylamino)-propionic acid 
• 765922-56-3 isopropyl 3-amino-3-(3-fluorophenyl)propionate 
• 765922-57-4 s-butyl 3-amino-3-(3-fluorophenyl)propionate 
• 277745-43-4 3-amino-3-(3-fluorophenyl)propionic acid methyl ester 
• 723284-81-9 (R)-3-amino-3-(3-fluoro-phenyl)-propionic acid 
• 723284-79-5 (S)-3-amino-3-(3'-fluorophenyl)propanoic acid 
• 20595-30-6 3-Fluorocinnamic acid 
• 19883-77-3 L-3-fluorophenylalanine 
• 1257211-78-1 (R)-1-[3-benzamido-3-(3-fluorophenyl)propanamido]-3-methylbutylboronic acid 
• 1269634-16-3 methyl 3-benzamido-3-(3-fluorophenyl)propanoate 
• 1257212-46-6 3-benzamido-3-(3-fluorophenyl)propanoic acid 
• 182199-73-1 ethyl (+/-)-3-amino-3-(3-fluorophenyl)propanoate hydrochloride 
• 117291-32-4 3-(3-Fluoro-phenyl)-3-(2,2,2-trifluoro-acetylamino)-propionyl chloride 

Relevant academic research and scientific papers

Iridium-catalysed C-H borylation of β-aryl-aminopropionic acids

Iridium-catalysed catalytic, regioselective C-H borylation of β-aryl-aminopropionic acid derivatives gives access to 3,5-functionalised protected β-aryl-aminopropionic acid boronates. The synthetic versatility of these new boronates is demonstrated through sequential one-pot functionalisation reactions to give diverse building blocks for medicinal chemistry. The C-H borylation is also effective for dipeptide substrates. We have exemplified this methodology in the synthesis of a pan αv integrin antagonist.

Kinetic Resolution of Aromatic β-Amino Acids Using a Combination of Phenylalanine Ammonia Lyase and Aminomutase Biocatalysts

An enzymatic strategy for the preparation of (R)-β-arylalanines employing phenylalanine aminomutase and ammonia lyase (PAM and PAL) enzymes has been demonstrated. Candidate PAMs with the desired (S)-selectivity from Streptomyces maritimus (EncP) and Bacillus sp. (PabH) were identified via sequence analysis using a well-studied template sequence. The newly discovered PabH could be linked to the first ever proposed biosynthesis of pyloricidin-like secondary metabolites and was shown to display better β-lyase activity in many cases. In spite of this, a method combining the higher conversion of EncP with a strict α-lyase from Anabaena variabilis (AvPAL) was found to be more amenable, allowing kinetic resolution of five racemic substrates and a preparative-scale reaction with >98% (R) enantiomeric excess. This work represents an improved and enantiocomplementary method to existing biocatalytic strategies, allowing simple product separation and modular telescopic combination with a preceding chemical step using an achiral aldehyde as starting material. (Figure presented.).

Synthesis and biological evaluation of 3-phenyl-3-aryl carboxamido propanoic acid derivatives as small molecule inhibitors of retinoic acid 4-hydroxylase (CYP26A1)

All-trans-retinoic acid (ATRA), the biologically active metabolite of vitamin A, is used medicinally for the treatment of hyperproliferative diseases and cancers. However, it is easily metabolized. In this study, the leading compound S8 was found based on virtual screening. To improve the activity of the leading compound S8, a series of novel S8 derivatives were designed, synthesized and evaluated for their in vitro biological activities. All of the prepared compounds showed that substituting the 5-chloro-3-methyl-1-phenyl-1H-pyrazole group for the 2-tertbutyl-5-methylfuran scaffold led to a clear increase in the biological activity. The most promising compound 32, with a CYP26A1 IC50 value of 1.36 μM (compared to liarozole (IC50 = 2.45 μM) and S8 (IC50 = 3.21 μM)) displayed strong inhibitory and differentiation activity against HL60 cells. In addition, the study focused on the effect of β-phenylalanine, which forms the coordination bond with the heme of CYP26A1. These studies suggest that the compound 32 can be used as an appropriate candidate for future development.

Structure activity relationships of αv integrin antagonists for pulmonary fibrosis by variation in aryl substituents

Antagonism of αvβ6 is emerging as a potential treatment of idiopathic pulmonary fibrosis based on strong target validation. Starting from an αvβ3 antagonist lead and through simple variation in the nature and position of the aryl substituent, the discovery of compounds with improved αvβ6 activity is described. The compounds also have physicochemical properties commensurate with oral bioavailability and are high quality starting points for a drug discovery program. Compounds 33S and 43E1 are pan αv antagonists having ca. 100 nM potency against αvβ3, αvβ5, αvβ6, and αvβ8 in cell adhesion assays. Detailed structure activity relationships with these integrins are described which also reveal substituents providing partial selectivity (defined as at least a 0.7 log difference in pIC50 values between the integrins in question) for αvβ3 and αvβ5.

Stereoselective chemoenzymatic preparation of β-amino esters: Molecular modelling considerations in lipase-mediated processes and application to the synthesis of (S)-dapoxetine

A wide range of optically active 3-amino-3-arylpropanoic acid derivatives have been prepared by means of a stereoselective chemoenzymatic route. The key step is the kinetic resolution of the corresponding β-amino esters. Although the enzymatic acylations of the amino group with ethyl methoxyacetate showed synthetically useful enantioselectivities, the hydrolyses of the ester group catalyzed by lipase from Pseudomonas cepacia have been identified as the optimal processes concerning both activity and enantioselectivity. The enantiopreference of this lipase in these reactions has been explained, at the molecular level, by using a fragment-based approach in which the most favoured binding site for a phenyl ring and the most stable conformation of the 3-aminopropanoate core nicely match the (S)-configuration of the major products. The conversion and enantioselectivity values of the enzymatic reactions have been compared in order to understand the influence of the different substitution patterns present in the phenyl ring. This chemoenzymatic route has been successfully applied to the preparation of a valuable intermediate in the synthesis of (S)-dapoxetine, which has been chemically synthesised in excellent optical purity.

Phenylalanine aminomutase-catalyzed addition of ammonia to substituted cinnamic acids: A route to enantiopure α- and β-amino acids

(Chemical Equation Presented) An approach is described for the synthesis of aromatic α- and β-amino acids that uses phenylalanine aminomutase to catalyze a highly enantioselective addition of ammonia to substituted cinnamic acids. The reaction has a broad scope and yields substituted α- and β-phenylalanines with excellent enantiomeric excess. The regioselectivity of the conversion is determined by substituents present at the aromatic ring. A box model for the enzyme active site is proposed, derived from the influence of the hydrophobicity of substituents on the enzyme affinity toward various substrates.

An efficient new enzymatic method for the preparation of β-aryl-β-amino acid enantiomers

An efficient synthesis of β-aryl-β-amino acid enantiomers has been developed via the lipase-catalysed enantioselective hydrolysis of the corresponding racemic ethyl esters in an organic solvent. High enantioselectivities (E >100) were observed when the lipase PS-catalysed reactions were performed with H2O (0.5 equiv) in diisopropyl ether at 45 °C. The products could be easily separated and were obtained in good yields of ≥40%.

3-AMINO-3-ARYLPROPIONIC ACID n-ALKYL ESTERS, PROCESS FOR PRODUCTION THEREOF, AND PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE 3-AMINO-3-ARYLPROPIONIC ACIDS AND ESTERS OF THE ANTIPODES THERETO

The present invention is to provide an n-alkyl 3-amino-3-arylpropionate represented by the formula (I): wherein Ar1 represents an aryl group which may have a substituent(s), provided that a phenyl group and 4-methoxyphenyl group are excluded, R1 represents an n-propyl group or an n-butyl group, and a process for preparing the same, and its optically active compound and an optically active (S or R)-3-amino-3-arylpropionic acid represented by the formula (III-a): wherein Ar represents an aryl group which may have a substituent(s), and * represents an asymmetric carbon, and a process for preparing an optically active n-alkyl (R or S)-3-amino-3-arylpropionate represented by the formula (IV-a): wherein Ar and R1 have the same meanings as defined above, * represents an asymmetric carbon, provided that it has a reverse absolute configuration to the compound of the formula (III-a).

Structure-activity relationships of 1,3,5-triazine-2,4,6-triones as human gonadotropin-releasing hormone receptor antagonists

SAR studies of 1,3,5-triazine-2,4,6-triones as human gonadotropin-releasing hormone receptor antagonists resulted in potent compounds. The best compound from the series had a binding affinity of 2 nM.

Une synthese simple des premieres amino-3 indanones-1

The synthesis of various substituted 3-amino-1-indanones was achieved in five steps starting from corresponding benzaldehydes.