862414-80-0

Upstream product

• 328273-02-5 (2R,5S)-methyl 5-(benzyloxycarbonylamino)-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanoate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 328273-06-9 C₁₆H₂₂FNO₃ 
• 1426814-68-7 (2R)-2-bromo-3-(4-fluorophenyl)propanoic acid 
• 18125-46-7 (R)-4-fluorophenylalanine 
• 191731-16-5 (S)-tert-butyl 4-(benzyloxycarbonyl)amino-5-methyl-3-oxohexanoate 
• 1149-26-4 (S)-N-(benzyloxycarbonyl)valine 
• 328273-04-7 (2R)-3-(4-Fluorophenyl)-2-trifluoromethane-sulfonyloxypropionic Acid Methyl Ester 
• 124980-98-9 (R)-methyl 3-(4-fluorophenyl)-2-hydroxypropanoate 

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 
• 862414-84-4 allyl (2R,5S)-2-(4-fluorobenzyl)-6-methyl-5-{[(5-methyl-3-isoxazolyl)carbonyl]amino}-4-oxoheptanoate 
• 862414-82-2 allyl (2R,5S)-5-(tert-butoxycarbonyl)amino-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanoate 
• 328086-55-1 (2R,5S)-2-(4-Fluoro-benzyl)-6-methyl-5-[(5-methyl-isoxazole-3-carbonyl)-amino]-4-oxo-heptanoic acid 
• 223526-67-8 (2R,5S)-5-(tert-butoxycarbonylamino)-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanic acid 

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.