328086-57-3

Usage

Uses

Used in Pharmaceutical Industry:
(4R)-N-(tert-Butyloxycarbonyl)-4-(cyanoMethyl)-L-glutaMic Acid 1,5-DiMethyl Ester is used as a key intermediate compound in the synthesis of protease inhibitors. Protease inhibitors are essential in the development of drugs targeting various diseases, including cancer, viral infections, and inflammatory conditions. (4R)-N-(tert-Butyloxycarbonyl)-4-(cyanoMethyl)-L-glutaMic Acid 1,5-DiMethyl Ester's unique structure allows for the creation of potent and selective inhibitors, which can help in the treatment of these diseases by blocking the action of specific proteases.
In the preparation of protease inhibitors, (4R)-N-(tert-Butyloxycarbonyl)-4-(cyanoMethyl)-L-glutaMic Acid 1,5-DiMethyl Ester serves as a building block that can be further modified and optimized to enhance the potency, selectivity, and pharmacokinetic properties of the final drug candidate. This makes it a valuable asset in the drug discovery and development process, contributing to the advancement of novel therapeutics for various medical conditions.

Upstream product

• 590-17-0 cyanomethyl bromide 
• 24424-99-5 di-tert-butyl dicarbonate 
• 624-75-9 iodoacetonitrile 
• 59279-60-6 dimethyl (2S)-2-[(tert-butoxycarbonyl)amino]pentanedioate 
• 6525-53-7 L-glutamic acid dimethyl ester 
• 56-86-0 L-glutamic acid 

Downstream Products

• 799270-24-9 (S,E)-ethyl 4-((2R,5S)-5-(tert-butoxycarbonylamino)-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanamido)-5-((S)-2-oxopyrrolidin-3-yl)pent-2-enoate 
• 328086-61-9 ethyl (S,E)-4-((tert-butoxycarbonyl)amino)-5-((S)-2-oxopyrrolidin-3-yl)pent-2-enoate 
• 869494-42-8 (E)-(S)-4-{(2R,4S,5S)-2-Benzyl-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-5-[(5-methyl-isoxazole-3-carbonyl)-amino]-heptanoylamino}-5-((S)-2-oxo-pyrrolidin-3-yl)-pent-2-enoic acid ethyl ester 
• 869494-40-6 (E)-(S)-4-[(2R,4S,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-heptanoylamino]-5-((S)-2-oxo-pyrrolidin-3-yl)-pent-2-enoic acid ethyl ester 
• 869494-44-0 (E)-(S)-4-{(2R,4S,5S)-2-Benzyl-4-hydroxy-6-methyl-5-[(5-methyl-isoxazole-3-carbonyl)-amino]-heptanoylamino}-5-((S)-2-oxo-pyrrolidin-3-yl)-pent-2-enoic acid ethyl ester 
• 328086-54-0 (2E,4S)-4-(tert-butoxycarbonylamino)-5-[(3'S)-2'-oxo-3'-pyrrolidinyl]-2-pentenoic acid ethyl ester 
• 249736-45-6 [2-hydroxy-1S-(2-oxopyrrolidin-3S-ylmethyl)ethyl]carbamic acid tert-butyl ester 
• 328086-60-8 (2S)-2-(tert-butoxycarbonylamino)-3-[(3'S)-2'-oxo-3'-pyrrolidinyl]propanoic acid methy ester 
• 898264-61-4 methyl (5S,8S,11S)-5-((R)-1-(tert-butoxy)ethyl)-8-(cyclohexylmethyl)-3,6,9-trioxo-11-(((S)-2-oxopyrrolidin-3-yl)methyl)-1-phenyl-2-oxa-4,7,10-triazadodecan-12-oate 
• 898264-62-5 benzyl ((2S,3R)-3-(tert-butoxy)-1-(((S)-3-cyclohexyl-1-(((S)-1-hydroxy-3-((S)-2-oxopyrrolidin-3-yl)propan-2-yl)amino)-1-oxopropan-2-yl)amino)-1-oxobutan-2-yl)carbamate 
• 898264-60-3 2-(2-tert-butoxycarbonylamino-3-cyclohexyl-propionylamino)-3-(2-oxo-pyrrolidin-3-yl)-propionic acid methyl ester 

Relevant academic research and scientific papers

Design, synthesis, and biological evaluation of peptidomimetic aldehydes as broad-spectrum inhibitors against enterovirus and sars-cov-2

A novel series of peptidomimetic aldehydes was designed and synthesized to target 3C protease (3Cpro) of enterovirus 71 (EV71). Most of the compounds exhibited high antiviral activity, and among them, compound 18p demonstrated potent enzyme inhibitory activity and broad-spectrum antiviral activity on a panel of enteroviruses and rhinoviruses. The crystal structure of EV71 3Cpro in complex with 18p determined at a resolution of 1.2 ? revealed that 18p covalently linked to the catalytic Cys147 with an aldehyde group. In addition, these compounds also exhibited good inhibitory activity against the 3CLpro and the replication of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2), especially compound 18p (IC50 = 0.034 μM, EC50 = 0.29 μM). According to our previous work, these compounds have no reasons for concern regarding acute toxicity. Compared with AG7088, compound 18p also exhibited good pharmacokinetic properties and more potent anticoronavirus activity, making it an excellent lead for further development.

ANTIVIRAL COMPOUNDS FOR THE TREATMENT OF CORONAVIRUS, PICORNAVIRUS AND NOROVIRUS INFECTIONS

Provided herein are compounds of Formula (I), or pharmaceutically acceptable salts thereof, pharmaceutical compositions that include a compound described herein (including pharmaceutically acceptable salts of a compound described herein) and methods of synthesizing the same. Also provided herein are methods of treating coronavirus, Picomavirus and Norovims infections with a compound of Formula (I), or a pharmaceutically acceptable salt thereof.

KETOAMIDE COMPOUND AND PREPARATION METHOD, PHARMACEUTICAL COMPOSITION, AND USE THEREOF

A ketoamide compound and a preparation method, a pharmaceutical composition, and a use thereof. Specifically, the ketoamide compound shown in formula (A), a racemate, an enantiomer, or a diastereoisomer thereof, or any mixture of same, or a pharmaceutical

A Quick Route to Multiple Highly Potent SARS-CoV-2 Main Protease Inhibitors**

The COVID-19 pathogen, SARS-CoV-2, requires its main protease (SC2MPro) to digest two of its translated long polypeptides to form a number of mature proteins that are essential for viral replication and pathogenesis. Inhibition of this vital pr

PROTEASE INHIBITORS FOR TREATMENT OR PREVENTION OF CORONAVIRUS DISEASE

Provided are protease inhibitor compounds that find use in treating or preventing coronavirus disease. In some embodiments, the coronavirus disease is COVID-19. Also provided are compositions and kits comprising the compounds, as well methods of using the

α-Ketoamides as Broad-Spectrum Inhibitors of Coronavirus and Enterovirus Replication: Structure-Based Design, Synthesis, and Activity Assessment

The main protease of coronaviruses and the 3C protease of enteroviruses share a similar active-site architecture and a unique requirement for glutamine in the P1 position of the substrate. Because of their unique specificity and essential role in viral po

[...] compound for the preparation of a classical swine fever virus (ASFV) infection drug application (by machine translation)

The invention relates to peptide aldehyde compound I, compound II in preparation for treating swine fever virus (ASFV) infection the application of the medicament, and it also relates to various optical isomer, a pharmaceutically acceptable solvate and pr

Cyanohydrin as an anchoring group for potent and selective inhibitors of enterovirus 71 3C protease

Cyanohydrin derivatives as enterovirus 71 (EV71) 3C protease (3Cpro) inhibitors have been synthesized and assayed for their biochemical and antiviral activities. Compared with the reported inhibitors, cyanohydrins (1S,2S,2′S,5S)-16 and (1R,2S,2′S,5S)-16 exhibited significantly improved activity and attractive selectivity profiles against other proteases, which were a result of the specific interactions between the cyanohydrin moiety and the catalytic site of 3Cpro. Cyanohydrin as an anchoring group with high selectivity and excellent inhibitory activity represents a useful choice for cysteine protease inhibitors.

Improved synthesis of rupintrivir

An improved synthesis of rupintrivir (AG7088) was accomplished using three amino acids (l-glutamic acid, d-4-fluorophenylalanine, and l-valine) as the building blocks. The key fragment ketomethylene dipeptide isostere was constructed with the valine derivative and phenylpropionic acid derivative, followed by coupling with a lactam derivative and an isoxazole acid chloride to provide AG7088 totally in eight steps.

Novel CADD-based peptidyl vinyl ester derivatives as potential proteasome inhibitors

A series of peptidyl vinyl ester derivatives bearing three different P1 substitutions as potential proteasome inhibitors were studied. The target molecules were designed based on CADD (computer aided drug design) protocol and synthesized. Their activities