beta-Lactam derivatives as enzyme inhibitors: derivatives of (E)-2-[(RS)-1-(4-methoxyphenyl)-2-oxo-4-phenylazetidin-3-ylidene]propionic acid.
The 1,4-diaryl disubstituted azetidin-2-one (beta-lactam) 1 is transformed into the 3-methylidene derivative (E)-2-[(RS)-1-(4-methoxyphenyl)-2-oxo-4-phenylazetidin-3-ylidene]propionic acid (3), and then, using the DCC/NHS method reacted with amino acid esters and dipeptide esters forming 3-(peptidyl)-beta-lactams 5 and 7. Structures and properties are evaluated mainly by spectroscopic methods and discussed. As molecular modeling experiments might suggest a potential activity as inhibitors of PPE(HLE), a number of selected compounds has been tested in an enzyme assay. But none of them showed any remarkable inhibitory activity. Evaluation of the data was done with the new program EnKinPlot.
Venz
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Department of Pharmaceutical/Medicinal Chemistry, Institute of Pharmacy, Ernst-Moritz-Arndt-University Greifswald, Germany.
Otto
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D000596:Amino Acids / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000494:pharmacology*; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010196:Pancreatic Elastase / Q000037:antagonists & inhibitors; D015842:Serine Proteinase Inhibitors / Q000494:pharmacology*; D047090:beta-Lactams
D000596:Amino Acids; D000900:Anti-Bacterial Agents; D015842:Serine Proteinase Inhibitors; D047090:beta-Lactams; D010196:Pancreatic Elastase