Modifications of the C6-substituent of penicillin sulfones with the goal of improving inhibitor recognition and efficacy

Nottingham, Micheal; Bethel, Christopher R.; Pagadala, Sundar Ram Reddy; Harry, Emily; Pinto, Abishai; Lemons, Zachary A.; Drawz, Sarah M.; Akker, F. van den; Carey, Paul R.; Buynak, John D.

doi:10.1016/j.bmcl.2010.10.134

Cited by 18 publications

(4 citation statements)

References 33 publications

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“…Better results were obtained using [Pd{P(o-Tol) 3 } 2 Cl 2 ]r ather than [Pd(PPh 3 ) 2 Cl 2 ]. In similar fashion, compounds 8k/8l could be synthesized in high yields.T hese two systems feature heterocyclic cores of biological and pharmacological relevance, [17] and feature in oxacilin antibiotic derivatives 18 and in the serotonin receptor antagonist granisetron. [16] Remarkably,h alo,n itrile, ester,a nd nitro functionalities,a nd even the pendant aldehyde function in 8b,r emained untouched during borylation.…”

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confidence: 99%

Catalytic Borylation using an Air‐Stable Zinc Boryl Reagent: Systematic Access to Elusive Acylboranes

Campos

Aldridge

2015

Angew Chem Int Ed

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The use of borylzinc reagents in palladium-catalyzed borylation chemistry is described (i.e. a boron analogue of the Negishi coupling), including a one-pot bench-top protocol using an air- and moisture-stable bis(boryl)zinc reagent. The steric/electronic properties of the boryl fragment employed enable a systematic method for accessing acylboranes, a rare class of organoboron species with great potential in chemical synthesis. The reactions proceed under mild conditions, use inexpensive commercial sources of palladium, and demonstrate a remarkable functional-group tolerance.

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confidence: 99%

Catalytic Borylation using an Air‐Stable Zinc Boryl Reagent: Systematic Access to Elusive Acylboranes

Campos

Aldridge

2015

Angew Chem Int Ed

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“…In addition, the reaction proceeds equally well for aliphatic acyl chlorides,a nd even the reactive cyclopropanecarbonyl chloride (7i)w as successfully borylated. In similar fashion, compounds 8k/8l could be synthesized in high yields.T hese two systems feature heterocyclic cores of biological and pharmacological relevance, [17] and feature in oxacilin antibiotic derivatives 18 and in the serotonin receptor antagonist granisetron. [19] Table 1: Substrate scope for the borylation of aryl and related bromides using the [Pd(PPh 3 ) 2 Cl 2 ]/3 system.…”

Section: Methodsmentioning

confidence: 99%

Catalytic Borylation using an Air‐Stable Zinc Boryl Reagent: Systematic Access to Elusive Acylboranes

Campos

Aldridge

2015

Angewandte Chemie

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The use of borylzinc reagents in palladium-catalyzed borylation chemistry is described (i.e.aboron analogue of the Negishi coupling), including ao ne-pot bench-top protocol using an air-a nd moisture-stable bis(boryl)zinc reagent. The steric/electronic properties of the boryl fragment employed enable as ystematic method for accessing acylboranes,arare class of organoboron species with great potential in chemical synthesis.T he reactions proceed under mild conditions,u se inexpensive commercial sources of palladium, and demonstrate ar emarkable functional-group tolerance.

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“…The inhibitors of β-lactamase are recognized to be in similar fashion as the substrate of β-lactamases. Such structural similarity may advantageously make it difficult for the microorganism to develop inhibitor resistance while maintaining recognition [18] .…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis and biological evaluation of sulfenimine cephalosporin analogues as β-lactamase inhibitors

Zhang

Ding

Shi

et al. 2015

Chem. Res. Chin. Univ.

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A series of sulfenimine cephalosporin derivatives(6a-6t) was designed, synthesized and evaluated for their inhibitory activity against class A β-lactamase(TEM-1) derived from E. coli, and class C β-lactamase (cephalosporinase) derived from wild Bacillus subtilis in cell-free systems. Most of the tested compounds showed enhanced inhibitory activity against class C β-lactamase(cephalosporinase) compared with tazobactam. The most promising compounds 6c and 6o in combination with cefradine(IC 50 =1.80 and 1.59 μmol/L, respectively) were further investigated against a series of clinical isolated β-lactamase-producing bacterial strains. The results reveal that compounds 6c and 6o in combination with cefradine show two to four times more activity than cefradine alone against methicillin-sensitive Staphylococcus aureus(MSSA) and Klebsiella pneumoniae. The data suggest that the sulfenimine moiety may be beneficial to the activity and selectivity of inhibitors.

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Modifications of the C6-substituent of penicillin sulfones with the goal of improving inhibitor recognition and efficacy

Cited by 18 publications

References 33 publications

Catalytic Borylation using an Air‐Stable Zinc Boryl Reagent: Systematic Access to Elusive Acylboranes

Catalytic Borylation using an Air‐Stable Zinc Boryl Reagent: Systematic Access to Elusive Acylboranes

Catalytic Borylation using an Air‐Stable Zinc Boryl Reagent: Systematic Access to Elusive Acylboranes

Design, synthesis and biological evaluation of sulfenimine cephalosporin analogues as β-lactamase inhibitors

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