328086-61-9

Usage

Uses

Used in Pharmaceutical Industry:
(2E,4S)-4-AMino-5-[(3S)-2-oxo-3-pyrrolidinyl]-2-pentenoic Acid Ethyl Ester is used as a key intermediate in the synthesis of Rhinovirus protease inhibitors. These inhibitors play a crucial role in the development of antiviral drugs targeting Rhinoviruses, which are responsible for causing the common cold and other respiratory illnesses.
By inhibiting the protease enzyme, (2E,4S)-4-AMino-5-[(3S)-2-oxo-3-pyrrolidinyl]-2-pentenoic Acid Ethyl Ester can help prevent the replication and spread of the virus, thereby reducing the severity and duration of infections. The development of such inhibitors is essential in the ongoing battle against viral infections, especially in the context of emerging and re-emerging viral diseases.

Upstream product

• 328086-54-0 (2E,4S)-4-(tert-butoxycarbonylamino)-5-[(3'S)-2'-oxo-3'-pyrrolidinyl]-2-pentenoic acid ethyl ester 
• 56-86-0 L-glutamic acid 
• 6525-53-7 L-glutamic acid dimethyl ester 
• 59279-60-6 dimethyl (2S)-2-[(tert-butoxycarbonyl)amino]pentanedioate 
• 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 
• 328086-60-8 (2S)-2-(tert-butoxycarbonylamino)-3-[(3'S)-2'-oxo-3'-pyrrolidinyl]propanoic acid methy ester 
• 249736-45-6 [2-hydroxy-1S-(2-oxopyrrolidin-3S-ylmethyl)ethyl]carbamic acid tert-butyl ester 
• 1025451-28-8 tert-butyl ((S)-1-oxo-3-((S)-2-oxopyrrolidin-3-yl)propan-2-yl)carbamate 

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 
• 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 
• 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

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.

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

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.

Protease inhibitors

This invention relates to treating an infection with a virus using protease inhibitors. Examples of the protease inhibitors include compounds of formula (I). Each variable is defined in the specification.

Structure-based design of a parallel synthetic array directed toward the discovery of irreversible inhibitors of human rhinovirus 3C protease

Utilizing the tools of parallel synthesis and structure-based design, a new class of Michael acceptor-containing, irreversible inhibitors of human rhinovirus 3C protease (HRV 3CP) was discovered. These inhibitors are shown to inhibit HRV-14 3CP with rates

Antipicornaviral compounds and compositions, their pharmaceutical uses, and materials for their synthesis

Compounds of the formula: where the formula variables are as defined herein, are disclosed that advantageously inhibit or block the biological activity of the picornaviral 3C protease. Also disclosed are compounds of the formula: where the formula variables are as defined herein that advantageously inhibit or block the biological activity of the picornaviral 3C protease. These compounds, as well as pharmaceutical compositions containing these compounds, are useful for treating patients or hosts infected with one or more picornaviruses, such as rhinovirus 3C proteases. Intermediates and synthetic methods for preparing such compounds are also described.