249736-45-6

Usage

Uses

Used in Pharmaceutical Industry:
N-[(1S)-1-(HydroxyMethyl)-2-[(3S)-2-oxo-3-pyrrolidinyl]ethyl]-carbaMic Acid tert-Butyl Ester is used as a key intermediate in the synthesis of Rhinovirus protease inhibitors for the treatment of viral infections, particularly the common cold caused by Rhinoviruses. Its chemical properties make it a suitable candidate for the development of antiviral drugs.
Used in Chemical Research:
As a complex organic molecule, N-[(1S)-1-(HydroxyMethyl)-2-[(3S)-2-oxo-3-pyrrolidinyl]ethyl]-carbaMic Acid tert-Butyl Ester can also be used in chemical research to study its reactivity, stability, and potential applications in various chemical processes and reactions. This may lead to the discovery of new compounds and materials with diverse applications.

Upstream product

• 112418-19-6 (R)-2-N-tert-butoxycarbonylamino-3-(tert-butyldimethylsilyloxy)propionic acid methyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 95715-85-8 2-(tert-butoxycarbonylamino)-3-hydroxypropionic acid methyl ester 
• 328086-58-4 (2S,4S)-2-(2-Amino-ethyl)-4-tert-butoxycarbonylamino-pentanedioic acid dimethyl ester 
• 328086-57-3 (2S,4S)-2-tert-butoxycarbonylamino-4-cyanomethyl-pentadioic acid dimethyl ester 
• 59279-60-6 dimethyl (2S)-2-[(tert-butoxycarbonyl)amino]pentanedioate 
• 6525-53-7 L-glutamic acid dimethyl ester 
• 56-86-0 L-glutamic acid 
• 328086-60-8 (2S)-2-(tert-butoxycarbonylamino)-3-[(3'S)-2'-oxo-3'-pyrrolidinyl]propanoic acid methy ester 

Downstream Products

• 328086-54-0 (2E,4S)-4-(tert-butoxycarbonylamino)-5-[(3'S)-2'-oxo-3'-pyrrolidinyl]-2-pentenoic acid ethyl ester 
• 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 
• 422323-15-7 (1''S,1''''S,3'''''S)-5-methylisoxazole-3-carboxylic acid (1'-{2''-(3''',4'''-difluorophenyl)-1''-[2''''-hydroxy-1''''-(2'''''-oxopyrrolidin-3'''''-ylmethyl)ethylcarbamoyl]ethyl}-2'-oxo-1',2'-dihydropyridin-3'-yl)amide 
• 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 

Relevant academic research and scientific papers

An efficient synthesis of a key intermediate for the preparation of the rhinovirus protease inhibitor AG7088 via asymmetric dianionic cyanomethylation of N-Boc-L-(+)-glutamic acid dimethyl ester

An efficient synthetic route to a key intermediate for the preparation of the rhinovirus protease inhibitor AG7088 has been developed employing a key asymmetric dianionic cyanomethylation of N-Boc-L-(+)-glutamic acid dimethyl ester. This methodology enables the preparation of this compound in kilogram quantities with an overall yield of 30%.

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.

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

PEPTIDOMIMETICS FOR THE TREATMENT OF CORONAVIRUS AND PICORNAVIRUS INFECTIONS

Compounds, compositions and methods for preventing, treating or curing a coronavirus, picornavirus, and/or Hepeviridae virus infection in human subjects or other animal hosts. Specific viruses that can be treated include enteroviruses. In one embodiment, the compounds can be used to treat an infection with a severe acute respiratory syndrome virus, such as human coronavirus 229E, SARS, MERS, SARS-CoV-1 (OC43), and SARS-CoV- 2. In another embodiment, the methods are used to treat a patient co-infected with two or more of these viruses, or a combination of one or more of these viruses and norovirus.

PEPTIDOMIMETICS FOR THE TREATMENT OF NOROVIRUS INFECTION

The present invention is directed to compounds, compositions and methods for preventing, treating or curing Norovirus infection in human subjects or other animal hosts.

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

Inhibition of the severe acute respiratory syndrome 3CL protease by peptidomimetic α,β-unsaturated esters

The proteolytic processing of polyproteins by the 3CL protease of severe acute respiratory syndrome coronavirus is essential for the viral propagation. A series of tripeptide α,β-unsaturated esters and ketomethylene isosteres, including AG7088, are synthesized and assayed to target the 3CL protease. Though AG7088 is inactive (IC50 > 100 μM), the ketomethylene isosteres and tripeptide α,β-unsaturated esters containing both P1 and P2 phenylalanine residues show modest inhibitory activity (IC50 = 11-39 μM). The Phe-Phe dipeptide inhibitors 18a-e are designed on the basis of computer modeling of the enzyme-inhibitor complex. The most potent inhibitor 18c with an inhibition constant of 0.52 μM is obtained by condensation of the Phe-Phe dipeptide α,β-unsaturated ester with 4-(dimethylamino)cinnamic acid. The cell-based assays also indicate that 18c is a nontoxic anti-SARS agent with an EC50 value of 0.18 μM.

Design and synthesis of peptidomimetic severe acute respiratory syndrome chymotrypsin-like protease inhibitors

Design, synthesis, and biological evaluation of peptidomimetic severe acute respiratory syndrome chymotrypsin-like protease (SARS-3CLpro) inhibitors for severe acute respiratory syndrome coronavirus (SARS-CoV) are described. These inhibitors exhibited antiviral activity against SARS-CoV in infected cells in the micromolar range. An X-ray crystal structure of our lead inhibitor (4) bound to SARS-3CLpro provided important drug-design templates for the design of small-molecule inhibitors.