951174-48-4

Usage

Uses

Used in Pharmaceutical Industry:
(S)-3-amino-3-(4-biphenyl)propanoic acid is used as a key intermediate for the synthesis of various pharmaceutical compounds due to its unique structure and chiral properties. Its incorporation into drug molecules can potentially enhance their efficacy and selectivity, leading to improved therapeutic outcomes.
Used in Chiral Synthesis Research:
As a chiral molecule, (S)-3-amino-3-(4-biphenyl)propanoic acid is used as a model compound in the study of chiral synthesis. Researchers utilize it to develop new methods and techniques for the synthesis of enantiomerically pure compounds, which are essential in the pharmaceutical industry to avoid the potential adverse effects of their mirror images.
Used in Organic Chemistry Research and Development:
(S)-3-amino-3-(4-biphenyl)propanoic acid serves as a useful building block in the synthesis of a variety of organic compounds. Its unique structure allows for the creation of novel molecules with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.
Used in Drug Design and Development:
(S)-3-amino-3-(4-biphenyl)propanoic acid's specific properties and structure make it an attractive candidate for drug design and development. It can be used as a starting material or a structural component in the creation of new drugs, particularly those targeting specific biological receptors or pathways.

Upstream product

• 141-82-2 malonic acid 
• 3218-36-8 4-Phenylbenzaldehyde 
• 951174-42-8 tert-butyl (R)-3-amino-3-(4-biphenyl)propanoate 
• 951174-45-1 tert-butyl (S)-3-amino-3-(4-biphenyl)propanoate 
• 479591-57-6 3-amino-3-(4-biphenyl)propionic acid methyl ester 
• 910574-67-3 tert-butyl(E)-3-([1,1′-biphenyl]-4-yl)acrylate 
• 951174-33-7 tert-butyl (3S,αR)-3-(N-benzyl-N-α-methylbenzylamino)-3-(4-biphenyl)propanoate 
• 951174-25-7 tert-butyl (3R,αS)-3-(N-benzyl-N-α-methylbenzylamino)-3-(4-biphenyl)propanoate 

Relevant academic research and scientific papers

Catalytic asymmetric oxidative carbonylation-induced kinetic resolution of sterically hindered benzylamines to chiral isoindolinones

A highly enantioselective kinetic resolution of sterically hindered benzylamines has been achieved for the first time through transition-metal-catalyzed oxidative carbonylation, in which the new KR strategy offered a new approach to afford chiral isoindolinones (er up to 97?:?3) and the origin of chemoselectivity and stereoselectivity was confirmed by density functional theory (DFT) calculations.

Synthesis, molecular docking and biological evaluation of novel phthaloyl derivatives of 3-amino-3-aryl propionic acids as inhibitors of Trypanosoma cruzi trans-sialidase

In the last two decades, trans-sialidase of Trypanosoma cruzi (TcTS) has been an important pharmacological target for developing new anti-Chagas agents. In a continuous effort to discover new potential TcTS inhibitors, 3-amino-3-arylpropionic acid derivatives (series A) and novel phthaloyl derivatives (series B, C and D) were synthesized and molecular docking, TcTS enzyme inhibition and determination of trypanocidal activity were carried out. From four series obtained, compound D-11 had the highest binding affinity value (?11.1 kcal/mol) compared to reference DANA (?7.8 kcal/mol), a natural ligand for TS enzyme. Furthermore, the 3D and 2D interactions analysis of compound D-11 showed a hydrogen bond, π-π stacking, π-anion, hydrophobic and Van der Waals forces with all important amino acid residues (Arg35, Arg245, Arg314, Tyr119, Trp312, Tyr342, Glu230 and Asp59) on the active site of TcTS. Additionally, D-11 showed the highest TcTS enzyme inhibition (86.9% ± 5) by high-performance ion exchange chromatography (HPAEC). Finally, D-11 showed better trypanocidal activity than the reference drugs nifurtimox and benznidazole with an equal % lysis (63 ± 4 and 65 ± 2 at 10 μg/mL) and LC50 value (52.70 ± 2.70 μM and 46.19 ± 2.36 μM) on NINOA and INC-5 strains, respectively. Therefore, D-11 is a small-molecule with potent TcTS inhibition and a strong trypanocidal effect that could help in the development of new anti-Chagas agents.

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.

Parallel synthesis of homochiral β-amino acids

The parallel asymmetric synthesis of an array of 30 β-amino acids of high enantiomeric purity using the conjugate addition of homochiral lithium N-benzyl-N-(α-methylbenzyl)amide as the key step is accomplished. The experimental simplicity and highly practical nature of the protocol is demonstrated by the efficient parallel conversion of 15 α,β-unsaturated esters to both enantiomeric series of the corresponding β-amino acids in high overall yields and selectivities with minimal purification involved in each step of the reaction protocol.

A one-pot synthesis of 3-amino-3-arylpropionic acids

3-Aminopropionic acids (β-amino acids) are biologically active compounds of interest in medicinal and pharmaceutical chemistry. Twenty-one 3-amino-3-arylpropionic acids were synthesized via a facile one-pot synthesis. In addition, a series of mechanistic studies have been performed to optimize the production of these β-amino acids. The reaction mechanism of this one-pot synthesis of β-amino acids, as well as the electronic effect of para-substitution and the influence of solvent polarity on the proposed reaction mechanism are discussed.

Nanomolar small molecule inhibitors for ανβ6, ανβ5, and ανβ3 integrins

Integrin adhesion receptors frequently recognize a core amino acid sequence, Arg-Gly-Asp, in their target ligands. Inhibitors with the ability to inhibit one or a small subset of such RGD-dependent integrins have been invaluable in defining their biological function. Here, we have characterized low molecular weight inhibitors for their ability to specifically inhibit ανβ6 integrin, a fibronectin/tenascin receptor. As of yet, no nonpeptidic inhibitor of ανβ6 was known. New peptidomimetic and nonpeptidic compounds were examined in isolated integrin binding assays and in cell adhesion assays for their ability to block ανβ6, ανβ3, ανβ5, and αIIbβ3 integrins. The compounds are based on an aromatically substituted β amino acid or glutaric acid derivative as an acidic center and an aminopyridyl or guanidyl residue as a basic mimetic. We found several classes of inhibitors with different selectivities, especially mono- or biselectivity on the αν-integrins ανβ6 and ανβ3, and nanomolar activity. Furthermore, nearly all compounds are inactive on αIIbβ3. Compound 11 is the first specific, peptidomimetic inhibitor of the ανβ6 integrin receptor.

Solid-phase synthesis of a nonpeptide RGD mimetic library: New selective αvβ3 integrin antagonists

The solid-phase synthesis of a low molecular weight RGD mimetic library is described. Activities of the compounds in inhibiting the interaction of ligands, vitronectin and fibrinogen, with isolated immobilized integrins αvβ3 and αIIbβ3 were determined in a screening assay. Highly active and selective nonpeptide αvβ3 integrin antagonists with regard to orally bioavailability were developed, based on the aza-glycine containing lead compound 1. An important variation is the substitution of the aspartic amide of 1 by an aromatic residue. Furthermore, different guanidine mimetics have been incorporated to improve the pharmacokinetic profile. Exchange of the β-amino acid NH by a methylene moiety in one set of RGD mimetics leads to the azacarba analogue compounds representing a novel peptidomimetic approach, which should increase the metabolic stability.

SYNTHESIS OF 6-ARYL-4-HYDROXYPIPERIDIN-2-ONES AND A POSSIBLE APPLICATION TO THE SYNTHESIS OF A NOVEL HMG-CoA REDUCTASE INHIBITOR

A series of 6-aryl-4-hydroxypiperidin-2-ones (11a-11g) were synthesised with the key step being a Dieckmann cyclisation of the appropriate methyl 3-(ethoxycarbonylacetylamino)-3-(substituted) propionate (8a-8g) and this new synthetic route was successfully applied to the synthesis of 4-hydroxy-6-(2-phenylethyl)piperidin-2-one (11h).The application of this strategy to the synthesis of the putative HMG-CoA reductase inhibitor 6--4-hydroxypiperidin-2-one (11i) was attempted, but failed during the Dieckmann cyclisation of methyl 3-(ethoxycarbonylacetylamino)- 3-propionate (8i).An alternative synthesis of a 1:1 diastereomeric mixture of (11i) was achieved by the reductive cleavage of the isoxazoline (24) with Raney nickel.The mixture of diastereoisomers (11i) was inactive in-vitro and in-vivo (rat) against HMG-CoA reductase