223526-67-8

Usage

Uses

Used in Pharmaceutical Industry:
(αR)-α-[(3S)-3-(tert-ButyloxycarbonylaMino)-4-Methyl-2-oxopentyl]-4-fluoro-benzenepropanoic Acid is used as a key intermediate in the synthesis of rhinovirus protease inhibitors. These inhibitors are essential for the development of antiviral drugs targeting the human rhinovirus, which is a significant cause of the common cold and other respiratory illnesses.
Additionally, (αR)-α-[(3S)-3-(tert-ButyloxycarbonylaMino)-4-Methyl-2-oxopentyl]-4-fluoro-benzenepropanoic Acid is used as a building block in the preparation of peptidomimetic α,β-unsaturated esters. These esters have potential applications in the design and synthesis of novel peptide-based drugs, which can mimic the action of natural peptides with improved stability and bioavailability. This makes them valuable in the development of new therapeutic agents for various diseases and conditions.

Upstream product

• 124980-98-9 (R)-methyl 3-(4-fluorophenyl)-2-hydroxypropanoate 
• 328273-04-7 (2R)-3-(4-Fluorophenyl)-2-trifluoromethane-sulfonyloxypropionic Acid Methyl Ester 
• 328273-02-5 (2R,5S)-methyl 5-(benzyloxycarbonylamino)-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanoate 
• 18125-46-7 (R)-4-fluorophenylalanine 
• 1426814-68-7 (2R)-2-bromo-3-(4-fluorophenyl)propanoic acid 
• 328273-06-9 C₁₆H₂₂FNO₃ 
• 1426814-56-3 (R)-methyl 2-bromo-3-(4-fluorophenyl)propanoate 
• 214286-60-9 trans-(1'R,2S,2'R)-6-methyl-2-(4''-fluorobenzyl)hept-4-enoic acid (2'-hydroxy-1'-methyl-2-phenylethyl)methyl amide 
• 112375-59-4 trans-6-methylhept-4-enoic acid chloride 
• 61229-07-0 trans-6-methylhept-4-enoic acid 
• 799270-17-0 (4S,5S)-5-Dibenzylamino-4-hydroxy-6-methyl-hept-2-ynoic acid ethyl ester 
• 799270-15-8 (4R,5S)-5-Dibenzylamino-4-hydroxy-6-methyl-hept-2-ynoic acid ethyl ester 
• 799270-21-6 (4R,5S)-5-tert-Butoxycarbonylamino-4-methanesulfonyloxy-6-methyl-heptanoic acid ethyl ester 
• 799270-23-8 (4S,5S)-5-(2-Ethoxycarbonyl-ethyl)-4-isopropyl-2-oxo-oxazolidine-3-carboxylic acid tert-butyl ester 

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 
• 214286-70-1 ethyl-3--L-Phe(4-F)-L-(Tr-Gln)>-E-propenoate 
• 862414-84-4 allyl (2R,5S)-2-(4-fluorobenzyl)-6-methyl-5-{[(5-methyl-3-isoxazolyl)carbonyl]amino}-4-oxoheptanoate 
• 328086-55-1 (2R,5S)-2-(4-Fluoro-benzyl)-6-methyl-5-[(5-methyl-isoxazole-3-carbonyl)-amino]-4-oxo-heptanoic acid 
• 214286-66-5 ethyl-3--L-Phe(4-F)-L-(Tr-Gln)>-E-propenoate 
• 223526-69-0 ethyl-3--L-Phe(4-F)-L-<(N-2,4-dimethoxybenzyl)-(S)-Pyrrol-Ala>>-E-propenoate 
• 862414-82-2 allyl (2R,5S)-5-(tert-butoxycarbonyl)amino-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanoate 

Relevant academic research and scientific papers

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.

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.

An efficient and tunable route to AG7088, a rhinovirus protease inhibitor

Aldol reaction of N,N-dibenzyl valinal with propiolic acid ethyl ester derived lithium reagent provides anti-aminoalcohol 8 and syn-aminoalcohol 9, which are converted into the lactone 6 via two different routes. Alkylation of 6 followed by lactone ring o

Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. 3. Structure-activity studies of ketomethylene-containing peptidomimetics

The structure-based design, chemical synthesis, and biological evaluation of various ketomethylene-containing human rhinovirus (HRV) 3C protease (3CP) inhibitors are described. These compounds are comprised of a peptidomimetic binding determinant and an e