93709-65-0

Usage

Structure

2-(4-Methoxy-benzoylamino)-3-methyl-butyric acid consists of a butyric acid derivative with a benzene ring, a methoxy group, and an amide functional group.

Type of compound

It is a chemical compound.

Potential pharmaceutical applications

The compound may have potential uses in drug design or as a building block in organic synthesis due to its structural features.

Importance in research

The properties and potential uses of 2-(4-Methoxy-benzoylamino)-3-methyl-butyric acid make it significant for further research and development in the fields of medicinal chemistry and pharmaceuticals.

InChI:InChI=1/C13H17NO4/c1-8(2)11(13(16)17)14-12(15)9-4-6-10(18-3)7-5-9/h4-8,11H,1-3H3,(H,14,15)(H,16,17)/p-1/t11-/m1/s1

Upstream product

• 100-07-2 4-methoxy-benzoyl chloride 
• 516-06-3 D,L-valine 
• 251538-67-7 C₁₄H₁₉NO₄ 
• 72-18-4 L-valine 
• 100-09-4 4-methoxybenzoic acid 
• 696-62-8 para-iodoanisole 
• 18414-58-9 diphenylmethylsilanecarboxylic acid 
• 5619-05-6 DL-valine methyl ester hydrochloride 

Downstream Products

• 2108-54-5 1-(4-methoxyphenyl)pentane-1,4-dione 
• 79137-48-7 2-(4-methoxyphenyl)-5-oxo-4-iso-propyl-4,5-dihydrooxazole 
• 93709-96-7 4-MeOBz-D-Val-L-ValOMe 
• 93753-80-1 4-MeOBz-L-Val-L-ValOMe 

Relevant academic research and scientific papers

Asymmetric trifluoromethylthiolation of azlactones under chiral phase transfer catalysis

The first enantioselective method for the installation of the SCF3 group at the C-4 position of azlactones is described in the present communication under quinidinium phase transfer catalysis. The higher performance of substrates containing electron-rich 2-aryl groups at the azlactone was rationalized using DFT calculations.

Catalytic Aerobic Cross-Dehydrogenative Coupling of Azlactones en Route to α,α-Disubstituted α-Amino Acids

We developed a catalytic aerobic method to synthesize α,α-disubstituted α-amino acids through cross-dehydrogenative coupling of azlactones. Combining an iron catalyst with a bisoxazolidine ligand resulted in high catalytic performance, and cross-coupling with an indole proceeded smoothly under aerobic conditions. A wide variety of α-aryl and aliphatic amino acid derived azlactones were applied to the present catalysis. In addition, a quaternary carbon could be constructed using oxindole and benzofuranone under aerobic conditions.

A Novel N-Substituted Valine Derivative with Unique Peroxisome Proliferator-Activated Receptor γbinding Properties and Biological Activities

A proprietary library of novel N-Aryl-substituted amino acid derivatives bearing a hydroxamate head group allowed the identification of compound 3a that possesses weak proadipogenic and peroxisome proliferator-Activated receptor γ(PPARI) activating properties. The systematic optimization of 3a, in order to improve its PPARγagonist activity, led to the synthesis of compound 7j (N-Aryl-substituted valine derivative) that possesses dual PPARI/PPARα agonistic activity. Structural and kinetic analyses reveal that 7j occupies the typical ligand binding domain of the PPARγagonists with, however, a unique high-Affinity binding mode. Furthermore, 7j is highly effective in preventing cyclin-dependent kinase 5-mediated phosphorylation of PPARγserine 273. Although less proadipogenic than rosiglitazone, 7j significantly increases adipocyte insulin-stimulated glucose uptake and efficiently promotes white-To-brown adipocyte conversion. In addition, 7j prevents oleic acid-induced lipid accumulation in hepatoma cells. The unique biochemical properties and biological activities of compound 7j suggest that it would be a promising candidate for the development of compounds to reduce insulin resistance, obesity, and nonalcoholic fatty liver disease.

GRANZYME B DIRECTED IMAGING AND THERAPY

Provided herein are heterocyclic compounds useful for imaging Granzyme B. Methods of imaging Granzyme B, combination therapies, and kits comprising the Granzyme B imaging agents are also provided.

PEROXISOME PROLIFERATOR-ACTIVATED RECEPTOR GAMMA AGONISTS, METHOD OF PREPARATION AND USES THEREOF

The present invention relates to new peroxisome proliferator-activated receptor gamma (PPAR?) agonists, and their uses as in the prevention and/or treatment of type 2 diabetes, impaired glucose tolerance, insulin resistance syndrome, hyperlipidemia, metabolic syndrome, visceral obesity, obesity, hyperlipidemia and hypertriglyceridemia. The preparation said compounds is also described.

Palladium-Catalyzed Aminocarbonylation in Solid-Phase Peptide Synthesis: A Method for Capping, Cyclization, and Isotope Labeling

A new synthetic approach for introducing N-capping groups onto peptides attached to a solid support, combining aminocarbonylation under mild conditions using a palladacycle precatalyst and solid-phase peptide synthesis, is reported. The use of a silacarboxylic acid as an in situ CO-releasing molecule allowed the reaction to be performed in a single vial. The method also enables versatile substitution of side chains, side-chain-to-side-chain cyclizations, and selective [13C] acyl labeling of modified peptides.

Regiodivergent Enantioselective γ-Additions of Oxazolones to 2,3-Butadienoates Catalyzed by Phosphines: Synthesis of α,α-Disubstituted α-Amino Acids and N,O-Acetal Derivatives

Phosphine-catalyzed regiodivergent enantioselective C-2- and C-4-selective γ-additions of oxazolones to 2,3-butadienoates have been developed. The C-4-selective γ-addition of oxazolones occurred in a highly enantioselective manner when 2-aryl-4-alkyloxazol-5-(4H)-ones were employed as pronucleophiles. With the employment of 2-alkyl-4-aryloxazol-5-(4H)-ones as the donor, C-2-selective γ-addition of oxazolones took place in a highly enantioselective manner. The C-4-selective adducts provided rapid access to optically enriched α,α-disubstituted α-amino acid derivatives, and the C-2-selective products led to facile synthesis of chiral N,O-acetals and γ-lactols. Theoretical studies via DFT calculations suggested that the origin of the observed regioselectivity was due to the distortion energy that resulted from the interaction between the nucleophilic oxazolide and the electrophilic phosphonium intermediate.

Probing the efficiency of N-heterocyclic carbene promoted O- to C-carboxyl transfer of oxazolyl carbonates

(Chemical Equation Presented) Screening of a range of azolium salts, bases and solvents for reactivity indicates that triazolinylidenes, generated in situ with KHMDS in THF, promote the Steglich rearrangement of oxazolyl carbonates with high catalytic efficiency (typical reaction time 5 min at 1.5 mol % NHC). This protocol shows wide substrate applicability, even allowing the efficient generation of vicinal quaternary centers. An improved experimental procedure is also described that allows a simplified one-pot reaction protocol to be employed with similarly high catalytic efficiency.

Synthesis and aldose reductase inhibitory activity of benzoyl-amino acid derivatives

A series of N-(4-methoxy, 4-fluoro, 4-trifluoromethyl and 4-nitrobenzoyl)-L-amino acids was synthesized and their inhibitory activity towards bovine lens aldose reductase (ALR2) was tested.

N-TERMINAL SUBSTITUENT AND SIDE-CHAIN INFLUENCES ON THE CHEMICAL SHIFTS OF PROTONS IN MODEL DIPEPTIDE SYSTEMS

(1)H Chemical shift values of ester methyls in model dipeptide esters have been shown to be sensitive to (a) the nature and configuration of the constituent amino acids and (b) the spatial distance between the N-terminal aryl group and the ester protons.C