N-aryl 3-halogenated azetidin-2-ones and benzocarbacephems, inhibitors of beta-lactamases.

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Joyeau R, Molines H, Labia R, Wakselman M

N-aryl 3-halogenated azetidin-2-ones and benzocarbacephems, inhibitors of beta-lactamases.

J Med Chem. 1988 Feb;31(2):370-4.

PubMed ID

3257523 [ View in PubMed

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Abstract

N-(3-Carboxy-6-methylphenyl)-3-fluoroazetidin-2-one and a series of related N-aryl-3-halo- and -3,3-dihaloazetidinones 3, in which the halo substituent is a fluorine or a bromine atom, were prepared by using the Wasserman procedure of cyclization of beta-bromopropionamides as a key step. Their affinities for the TEM-1 beta-lactamase were determined and compared with those of a series of tricyclic azetidinones, the benzocarbacephems 2, and known beta-lactamase inhibitors. The beta-lactams 2 and 3 behave as competitive inhibitors and not as substrates of the enzyme; neither halogen substitution (series 3) nor ring strain (series 2) induces enzymatic hydrolysis.

DrugBank Data that Cites this Article

Drug Enzymes

Drug	Enzyme	Kind	Organism	Pharmacological Action	Actions
Benzylpenicillin	Beta-lactamase TEM	Protein	Escherichia coli	Unknown	Substrate	Details