86458-89-1

Upstream product

• 86449-83-4 (2-Oxo-4-phenyl-azetidin-1-yl)-acetic acid tert-butyl ester 
• 100-52-7 benzaldehyde 
• 40682-54-0 ethyl N-benzylideneglycinate 
• 5661-55-2 4-phenylazetidin-2-one 
• 303960-72-7 benzyl (RS)-2-(2-oxo-4-phenylazetidin-1-yl)acetate 
• 67077-19-4 ethyl (RS)-2-(2-oxo-4-phenylazetidin-1-yl)acetate 

Downstream Products

• 86458-99-3 3-[2-(2-Oxo-4-phenyl-azetidin-1-yl)-acetylamino]-propionic acid methyl ester 
• 86459-01-0 1,3-Dicyclohexyl-1-[2-(2-oxo-4-phenyl-azetidin-1-yl)-acetyl]-urea 
• 86458-98-2 2-(2-Oxo-4-phenyl-azetidin-1-yl)-N-phenyl-acetamide 
• 86458-97-1 1,3-Dicyclohexyl-1-[3-(2-furan-2-yl-4-oxo-azetidin-1-yl)-propionyl]-urea 
• 303960-93-2 {2-[(S,R)-2-oxo-4-phenylazetidin-1-yl]acetyl}-L-alanine phenyl ester 
• 303961-18-4 {2-[(S,R)-2-oxo-4-phenylazetidin-1-yl]acetyl}-L-valyl-L-alanine 2,2,2-trichloroethyl ester 
• 303961-29-7 {2-[(S,R)-2-oxo-4-phenylazetidin-1-yl]acetyl}-L-valyl-L-prolyl-L-alanine 2,2,2-trichloroethyl ester 

Relevant academic research and scientific papers

β-Lactam derivatives as enzyme inhibitors: Peptidic derivatives of (RS)-2-oxo-4-phenylazetidine-1-alkanoic acids

4-Phenylazetidine-2-one was transformed into 4-phenylazetidine-1-alkanoic acids, which were reacted in the presence of diphenylphosphoroazidate with amino acid esters and dipeptide esters yielding β-lactam peptides with different spacers between the lacta

β-Lactam derivatives as enzyme inhibitors: 1-Peptidyl derivatives of 4-phenylazetidin-2-one as inhibitors of elastase and papain

N-Peptidyl substituted azetidin-2-ones were synthesized and evaluated as inhibitors of the serine protease elastase, and the cysteine protease papain. All compounds were synthesized from 4-phenylazetidin-2-one, either from the racemate or from the pure enantiomers. The (S)-enantiomer was prepared by enantioselective synthesis from (S)-β-phenyl-β-alanine, while the (R)-enantiomer was obtained by enzymatic resolution with α-chymotrypsin. N-Alkylation with bromoacetates introduced a spacer group which, after hydrolysis to the free acid, was acylated with amino acid esters or di- or tripeptide esters. The enzymatic assays proved some derivatives to be effective inhibitors of PPE and/or papain. N-BOC protected amino acid derivatives without a spacer group inhibited PPE reversibly, while derivatives with spacer-group showed either weak or no inhibitory properties. On the other hand, papain was inactivated irreversibly by ethyl (RS)-2-oxo-4-phenylazetidin-1-acetate. The highest inhibitory activity against papain was found for the diastereomers of N-(2-oxo-4-phenylazetidin-1-acetyl)-L-alanyl-L-valine benzyl ester, a compound with a spacer group.