303960-75-0

Upstream product

• 67077-19-4 ethyl (RS)-2-(2-oxo-4-phenylazetidin-1-yl)acetate 
• 37088-64-5 (S)-4-phenyl-2-azetidinone 
• 37088-66-7 (3S)-methyl 3-amino-3-phenylpropanoate 
• 5661-55-2 4-phenylazetidin-2-one 
• 303960-70-5 ethyl (S)-2-(2-oxo-4-phenylazetidin-1-yl)acetate 

Downstream Products

• 303960-95-4 {2-[(S)-2-oxo-4-phenylazetidin-1-yl]acetyl}-L-alanine phenyl ester 
• 303961-20-8 {2-[(S)-2-oxo-4-phenylazetidin-1-yl]acetyl}-L-valyl-L-alanine 2,2,2-trichloroethyl ester 
• 303961-31-1 {2-[(S)-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: 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.