1988
DOI: 10.1021/jm00397a018
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N-Aryl 3-halogenated azetidin-2-ones and benzocarbacephems, inhibitors of .beta.-lactamases

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 comp… Show more

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Cited by 45 publications
(14 citation statements)
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“…Commonly, β- and γ-lactams are present in many natural products and pharmaceuticals, and the introduction of a gem -difluoromethylene moiety has been reported to improve their biological activities. For example, a gem -difluoro-γ-lactam can inhibit γ-lactamase, which is responsible for bacterial resistance to γ-lactam antibiotics [24]. Additionally, α,α-difluoro lactams are precursors of some biologically active compounds [58].…”
Section: Introductionmentioning
confidence: 99%
“…Commonly, β- and γ-lactams are present in many natural products and pharmaceuticals, and the introduction of a gem -difluoromethylene moiety has been reported to improve their biological activities. For example, a gem -difluoro-γ-lactam can inhibit γ-lactamase, which is responsible for bacterial resistance to γ-lactam antibiotics [24]. Additionally, α,α-difluoro lactams are precursors of some biologically active compounds [58].…”
Section: Introductionmentioning
confidence: 99%
“…X-ray crystal structure analysis of 5a (CCDC 989111): † formula C 12 General procedure for the synthesis of enamines Chiral secondary amine (1 equiv.) and dried solvent (3 mL) were placed in a glass pressure-vessel.…”
Section: Methodsmentioning
confidence: 99%
“…For example, gem-difluoro-glactam inhibits g-lactamase, an enzyme responsible for bacterial resistance to g-lactam antibiotics. 12 Moreover gem-difluoropropargyl amides are useful as suitable building blocks for the synthesis of fluorinated d-lactams via cycloisomerization. 13 Another example for application of the fluorine-containing compounds in synthesis is trifluoroacetamide analogues that serve as efficient enantioselective nucleophilic trifluoromethylating reagents.…”
Section: Introductionmentioning
confidence: 99%
“…[9] Few more structural analogs of sanfetrinem were synthesized and are known to possess a broad spectrum of antibacterial activities. [7a] Some tricyclic β-lactams acted as inhibitors of β-lactamases [10][11][12] and other medicinally relevant mammalian enzymes implicated in many diseases. [13,14] Thus, tricyclic β-lactams constituted a new generation of β-lactam antibiotics which are resistant to a wide range of β-lactamases and exhibit improved metabolic stability.…”
Section: Introductionmentioning
confidence: 99%