129095-62-1

Usage

Uses

Used in Pharmaceutical Industry:
TERT-BUTYL [(1R)-2-AMINO-1-BENZYL-2-OXOETHYL]CARBAMATE is used as a potential drug candidate for its unique molecular structure, which may offer novel therapeutic properties and applications in medicine.
Used in Synthesis of Bioactive Compounds:
In the pharmaceutical industry, TERT-BUTYL [(1R)-2-AMINO-1-BENZYL-2-OXOETHYL]CARBAMATE is used as a precursor in the synthesis of other bioactive compounds, leveraging its complex structure to create new molecules with potential medicinal value.
Further research is needed to fully understand the specific applications and benefits of TERT-BUTYL [(1R)-2-AMINO-1-BENZYL-2-OXOETHYL]CARBAMATE in various fields, particularly in the development of new pharmaceuticals and therapeutic agents.

Upstream product

• 18942-49-9 Boc-D-Phe-OH 
• 24424-99-5 di-tert-butyl dicarbonate 
• 5241-58-7 D-Phenylalaninamide 
• 19901-50-9 methyl (2R)-2-(t-butoxycarbonylamino)-3-phenylpropionate 
• 13033-84-6 D-phenylalanine methyl ester hydrochloride 

Downstream Products

• 71666-94-9 (R)-2-amino-3-phenylpropanamide hydrochloride 
• 400652-45-1 (R)-2-(tert-butoxycarbonylamino)-3-phenylpropionitrile 
• 129117-20-0 Z-Asn-D-Phe-NH₂ 
• 114112-92-4 [(S)-1-Carbamoyl-2-((R)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-ethyl]-carbamic acid benzyl ester 
• 129095-54-1 Z-Asp(OBu^t)-D-Phe-NH₂ 
• 1056903-99-1 6'-N-boc-(R)-phenylalanine-β-ICD 
• 28069-46-7 D-phenylalanine hydrochloride 
• 1312951-37-3 C₄₀H₄₆N₄O₄ 
• 1315334-25-8 (R)-tert-butyl 1-(4-carbamoylthiazol-2-yl)-2-phenylethylcarbamate 
• 1315334-26-9 (R)-tert-butyl 1-(4-cyanothiazol-2-yl)-2-phenylethylcarbamate 
• 1315334-27-0 (R)-2-(2-((R)-1-(tert-butoxycarbonylamino)-2-phenylethyl)thiazol-4-yl)-4-methyl-4,5-dihydrothiazole-4-carboxylic acid 
• 1315334-28-1 (S,E)-2-(trimethylsilyl)ethyl 3-((S)-2-((R)-2-(2-((R)-1-(tert-butoxycarbonylamino)-2-phenylethyl)thiazol-4-yl)-4-methyl-4,5-dihydrothiazole-4-carboxamido)-3-methylbutanoyloxy)-7-(tritylthio)hept-4-enoate 
• 1315334-29-2 C₄₇H₄₈N₄O₄S₃ 
• 1315334-20-3 (5R,8S,11S)-8-isopropyl-11-(4-mercaptobut-1-enyl)-5-methyl-10-oxa-3,17-dithia-7,14,19,20-tetraazatricyclo[14.2.1.1(2,5)]icosa-1⁽¹⁸⁾,2⁽²⁰⁾,16⁽¹⁹⁾-triene-6,9,13-trione 

Relevant academic research and scientific papers

Synthesis, anti-inflammatory and antimicrobial activities of new 1,2,4-oxadiazoles peptidomimetics

A new series of 1,2,4-oxadizoles 6a-g have been synthesised in good yields using the peptide synthesis strategy. The prepared compounds were tested for anti-inflammatory and antimicrobial activities. The anti-inflammatory activities were determined in the

Synthesis, in vitro ADME profiling and in vivo pharmacological evaluation of novel glycogen phosphorylase inhibitors

A small set of indole-2-carboxamide derivatives identified from a high-throughput screening campaign has been described as a novel, potent, and glucose-sensitive inhibitors of glycogen phosphorylase a (GPa). Among this series of compounds, compound 2 exhibited moderate GP inhibitory activity (IC50 = 0.29 μM), good cellular efficacy (IC50 = 3.24 μM for HepG2 cells and IC50 = 7.15 μM for isolated rat hepatocytes), together with good absorption, distribution, metabolism, and elimination (ADME) profiles. The in vivo animal study revealed that compound 2 significantly inhibited an increase of fasting blood glucose level in adrenaline-induced diabetic mice.

Mapping the s1 and s1’ subsites of cysteine proteases with new dipeptidyl nitrile inhibitors as trypanocidal agents

The cysteine protease cruzipain is considered to be a validated target for therapeutic intervention in the treatment of Chagas disease. A series of 26 new compounds were designed, synthesized, and tested against the recombinant cruzain (Cz) to map its S1/S1′ subsites. The same series was evaluated on a panel of four human cysteine proteases (CatB, CatK, CatL, CatS) and Leishmania mexicana CPB, which is a potential target for the treatment of cutaneous leishmaniasis. The synthesized compounds are dipeptidyl nitriles designed based on the most promising combinations of different moieties in P1 (ten), P2 (six), and P3 (four different building blocks). Eight compounds exhibited a Ki smaller than 20.0 nM for Cz, whereas three compounds met these criteria for LmCPB. Three inhibitors had an EC50 value of ca. 4.0 μM, thus being equipotent to benznidazole according to the antitrypanosomal effects. Our mapping approach and the respective structure-activity relationships provide insights into the specific ligand-target interactions for therapeutically relevant cysteine proteases.

Optimization strategy of single-digit nanomolar cross-class inhibitors of mammalian and protozoa cysteine proteases

Cysteine proteases (CPs) are involved in a myriad of actions that include not only protein degradation, but also play an essential biological role in infectious and systemic diseases such as cancer. CPs also act as biomarkers and can be reached by active-

Synthesis and structure-activity relationship of nitrile-based cruzain inhibitors incorporating a trifluoroethylamine-based P2 amide replacement

The structure-activity relationship for nitrile-based cruzain inhibitors incorporating a P2 amide replacement based on trifluoroethylamine was explored by deconstruction of a published series of inhibitors. It was demonstrated that the P3 biphenyl substituent present in the published inhibitor structures could be truncated to phenyl with only a small loss of affinity. The effects of inverting the configuration of the P2 amide replacement and linking a benzyl substituent at P1 were observed to be strongly nonadditive. We show that plotting affinity against molecular size provides a means to visualize both the molecular size efficiency of structural transformations and the nonadditivity in the structure-activity relationship. We also show how the relationship between affinity and lipophilicity, measured by high-performance liquid chromatography with an immobilized artificial membrane stationary phase, may be used to normalize affinity with respect to lipophilicity.

Amidation of carboxylic acids via the mixed carbonic carboxylic anhydrides and its application to synthesis of antidepressant (1S,2R)-tranylcypromine

Primary amidations of carboxylic acids 1 or 3 with NH4Cl in the presence of ClCO2Et and Et3N were developed to afford the corresponding primary amides in 22% to quantitative yields. Additionally, we have applied the amidation to the preparation of various amides containing hydroxamic acids and achieved the synthesis of (1S,2R)-tranylcypromine as an antidepressant medicine via Lossen rearrangement.

RITA Mimics: Synthesis and Mechanistic Evaluation of Asymmetric Linked Trithiazoles

The established cytotoxic agent RITA contains a thiophene-furan-thiophene backbone and two terminal alcohol groups. Herein we investigate the effect of using thiazoles as the backbone in RITA-like molecules and modifying the terminal groups of these trithiazoles, thereby generating 41 unique structures. Incorporating side chains with varied steric bulk allowed us to investigate how size and a stereocenter impacted biological activity. Subjecting compounds to growth inhibition assays on HCT-116 cells showed that the most potent compounds 7d, 7e, and 7h had GI50 values of 4.4, 4.4, and 3.4 μM, respectively, versus RITA (GI50 of 800 nM). Analysis of these compounds in apoptosis assays proved that 7d, 7e, and 7h were as effective as RITA at inducing apoptosis. Evaluating the impact of 7h on proteins targeted by RITA (p53, c-Myc, and Mcl-1) indicated that it acts via a different mechanism of action to that of RITA. RITA suppressed Mcl-1 protein via p53, whereas compound 7h suppressed Mcl-1 expression via an alternative mechanism independent of p53.

Synthesis of macrocycles that inhibit protein synthesis: Stereochemistry and structural based studies on sanguinamide B derivatives

We report the synthesis of seven new sanguinamide B (SanB) analogues. Substitution of amino acids along the backbone of SanB and testing in HCT-116 colon cancer cell lines identified new biologically active SanB derivatives. These compounds establish a st

Convenient preparation of primary amides via activation of carboxylic acids with ethyl chloroformate and triethylamine under mild conditions

Primary amides were easily prepared in 22-99% yields from the corresponding carboxylic acids 1 or 5 with NH4Cl via activation with ClCO 2Et and Et3N. The enantiomers of the corresponding primary amides of Cbz-, Boc-, or Fmoc-α-amino acids can be separated by using a chiral column.

Mechanistic studies of sanguinamide B derivatives: A unique inhibitor of eukaryotic ribosomes

Described are mechanistic studies of two Sanguinamide B (San B) derivatives. These compounds were identified as eukaryotic ribosomal inhibitors. Two biotinylated San B derivatives were synthesized and used to capture protein targets in a pull-down assay.