7662-76-2

Usage

Uses

Used in Pharmaceutical Research:
N-BENZYLGLYCINE TERT-BUTYL ESTER is used as a research compound for studying the structure-based characterization and optimization of novel hydrophobic binding interactions. This is particularly relevant in the development of pyrrolidine influenza neuraminidase inhibitors, which are crucial in the treatment of influenza.
In the pharmaceutical industry, N-BENZYLGLYCINE TERT-BUTYL ESTER serves as a valuable tool in the design and synthesis of new drugs targeting specific biological interactions. Its application in this field is primarily due to its ability to help researchers understand and manipulate hydrophobic binding interactions, which are essential for the development of effective drugs.
Additionally, N-BENZYLGLYCINE TERT-BUTYL ESTER may have potential applications in other areas of chemistry and materials science, although the provided materials do not specify these uses. Its versatility and unique properties make it a promising compound for further exploration and development in various scientific fields.

Upstream product

• 5292-43-3 bromoacetic acid tert-butyl ester 
• 100-46-9 benzylamine 
• 6456-74-2 Glycine tert-butyl ester 
• 100-52-7 benzaldehyde 
• 107-59-5 tert-Butyl chloroacetate 
• 1383445-35-9 di-tert-butyl N-benzyl-2-aminomalonate 
• 15960-79-9 di-tert-butyl 2-bromomalonate 
• 35059-50-8 t-butyl diazoacetate 
• 100-39-0 benzyl bromide 
• 16881-32-6 tert-butyl N-(benzyloxycarbonyl)glycinate 

Downstream Products

• 101820-40-0 N-benzyl-N--L-alanyl>glycine t-butyl ester 
• 92685-86-4 [Benzyl-((2S,3R)-2-bromo-3-hydroxy-butyryl)-amino]-acetic acid tert-butyl ester 
• 7662-78-4 N-acetyl-N-benzylglycine tert-butyl ester 
• 196212-64-3 Boc-Asa[α,β-(OMe)2]-(Bn)-Gly-OtBu 
• 185426-26-0 (Benzyl-benzyloxycarbonylmethyl-amino)-acetic acid tert-butyl ester 
• 198225-16-0 [Benzyl-((S)-1-{2-[((S)-sec-butyl)-(2,2-dimethyl-propionyl)-amino]-acetyl}-pyrrolidine-2-carbonyl)-amino]-acetic acid tert-butyl ester 
• 17136-36-6 N-benzylglycine 

Relevant academic research and scientific papers

Design, synthesis, and biological evaluation of 2,6,7-substituted pyrrolo[2,3-d]pyrimidines as cyclin dependent kinase inhibitor in pancreatic cancer cells

Pancreatic cancer is a highly malignant tumor, and more effective treatment is urgently needed to lengthen the life of patients. In this paper a class of new 2,6,7-substituted pyrrolo[2,3-d]pyrimidine derivatives of CDK 4/6 inhibitor ribociclib (1) was de

Structure-Activity Relationship Studies of Hydantoin-Cored Ligands for Smoothened Receptor

An underside binding site was recently identified in the transmembrane domain of smoothened receptor (SMO). Herein, we report efforts in the exploration of new insights into the interactions between the ligand and SMO. The hydantoin core in the middle of the parent compound was found to be highly conservative in chirality, ring size, and substituents. On each benzene at two ends, a plethora of variations, particularly halogen substitutions, were introduced and investigated. Analysis of the structure-activity relationship revealed miscellaneous halogen effects. The ligands with double halogen substituents exhibit remarkably enhanced potency, providing promising candidates that potentially overcome the common drug resistance and useful heavy-atom labeled chemical tools for co-crystallization studies of SMO.

Dynamics in Catalytic Asymmetric Diastereoconvergent (3 + 2) Cycloadditions with Isomerizable Nitrones and α-Keto Ester Enolates

Reaction design in asymmetric catalysis has traditionally been predicated on a structurally robust scaffold in both substrates and catalysts, to reduce the number of possible diastereomeric transition states. Herein, we present the stereochemical dynamics in the Ni(II)-catalyzed diastereoconvergent (3 + 2) cycloadditions of isomerizable nitrile-conjugated nitrones with α-keto ester enolates. Even in the presence of multiple equilibrating species, the catalytic protocol displays a wide substrate scope to access a range of CN-containing building blocks bearing adjacent stereocenters with high enantio- and diastereoselectivities. Our computational investigations suggest that the enantioselectivity is governed in the deprotonation process to form (Z)-Ni-enolates, while the unique syn addition is mainly controlled by weak noncovalent bonding interactions between the nitrone and ligand.

Selective Functionalization of Aliphatic Amines via Myoglobin-Catalyzed Carbene N-H Insertion

Engineered myoglobins have recently gained attention for their ability to catalyze a variety of abiological carbene transfer reactions including the functionalization of amines via carbene insertion into N-H bonds. However, the scope of myoglobin and other hemoprotein-based biocatalysts in the context of this transformation has been largely limited to aniline derivatives as the amine substrates and ethyl diazoacetate as the carbene donor reagent. In this report, we describe the development of an engineered myoglobin-based catalyst that is useful for promoting carbene N-H insertion reactions across a broad range of substituted benzylamines and α-diazo acetates with high efficiency (82-99percent conversion), elevated catalytic turnovers (up to 7,000), and excellent chemoselectivity for the desired single insertion product (up to 99percent). The scope of this transformation could be extended to cyclic aliphatic amines. These studies expand the biocatalytic toolbox available for the selective formation of C-N bonds, which are ubiquitous in many natural and synthetic bioactive compounds.

PEPTOID-BASED CHELATING LIGANDS FOR SELECTIVE METAL CHELATION

The present disclosure provides peptoid-based chelating ligands, corresponding cyclic peptoids, and methods of making thereof. Functional groups may be tailored for high metal binding affinity and selectivity. The side chains of a cyclic peptoid according to the present disclosure may be selected based on, for example, high affinity for actinide or other metal ions, selectivity for actinide or other metal ions, the ability to recover a metal once it is bound to the peptoid, and whether the overall peptoid should be hydrophobic or hydrophilic. Unlike siderophores, peptoid-based chelating ligands of the present disclosure are not readily hydrolyzed under physiological conditions. Therefore, peptoid-based chelating ligands may be, for example, used to treat actinide (e.g., iron and lead) poisoning in vivo. Moreover, peptoid-based chelating ligands of the present disclosure may be used for medical imaging, chelation therapy, drug delivery, and separation technologies, for example.

New advances in the synthesis of tripyridinophane macrocycles suitable to enhance the luminescence of Ln(III) ions in aqueous solution

A series of four new 18-membered hexaaza macrocyclic ligands bearing three endocyclic pyridine units and acetate or methylenephosphonate pendant arms has been prepared. The new synthetic procedure is based on the use of amine and diamine precursors incorporating masked carboxylate or phosphonate functions and on an efficient sodium template effect which controls the crucial macrocyclization step (yields of macrocyclization reactions: 62–88%). This procedure appears as a suitable alternative compared to the classical Richman-Atkins methodology generally used for the preparation of this class of macrocycles. As demonstrated with the EuIII and TbIII complexes derived from two ligands, these tripyridinophane chelators form luminescent and stable mononuclear LnIII complexes in aqueous solution at physiological pH. In such a medium, TbIII complexes exhibit a brightness of 1700 (λexc = 279 nm) and 3000 (λexc = 268 nm) M?1 cm?1.

3-SUBSTITUTED PIPERIDINE-2, 6-DIONES AND NON-COVALENT COMPLEXES WITH ALBUMIN

The present disclosure provides derivatives of 3-substituted piperidine-2, 6-diones, non-covalently bound complexes with serum albumin, pharmaceutical compositions of the same, and methods of use thereof. The non-covalently bound complexes are significant

ABIRATERONE DERIVATIVES AND NON-COVALENT COMPLEXES WITH ALBUMIN

The present disclosure provides derivatives of abiraterone, non-covalently bound complexes of the abiraterone derivatives with serum albumin, pharmaceutical compositions of the same, and methods of use thereof. The non-covalently bound complexes are significantly more water-soluble than abiraterone and are useful for the treatment of a disease or condition that can benefit from CYP17 inhibition, such as prostate cancer.

Base-promoted c→n acyl rearrangement: An unconventional approach to α-amino acid derivatives

We have discovered that N-alkyl aminomalonates undergo a fast and selective intramolecular C→N acyl rearrangement reaction in the presence of a strong base, leading to N-protected glycinates in excellent yield. Moreover, the fact that the reaction proceeds through a nucleophilic enolate intermediate has been used for implementing a tandem rearrangement/alkylation sequence that has been applied to the preparation of synthetically relevant nonproteinogenic tertiary and quaternary N-alkyl α-amino acids in a very simple and reliable way.

Tailoring cytotoxicity of antimicrobial peptidomimetics with high activity against multidrug-resistant Escherichia coli

Infections with multidrug-resistant pathogens are an increasing concern for public health. Recently, subtypes of peptide-peptoid hybrids were demonstrated to display potent activity against multidrug-resistant Gram-negative bacteria. Here, structural variation of these antibacterial peptidomimetics was investigated as a tool for optimizing cell selectivity. A protocol based on dimeric building blocks allowed for efficient synthesis of an array of peptide-peptoid oligomers representing length variation as well as different backbone designs displaying chiral or achiral peptoid residues. Lack of α-chirality in the side chains of the peptoid residues proved to be correlated to reduced cytotoxicity. Furthermore, optimization of the length of these peptidomimetics with an alternating cationic-hydrophobic design was a powerful tool to enhance the selectivity against Gram-negative pathogens over benign mammalian cells. Thus, lead compounds with a high selectivity toward killing of clinically important multidrug-resistant E. coli were identified.