Cephalosporin, Carbapenem, and Monobactam Antibiotics

Thompson, Rodney L.

doi:10.1016/s0025-6196(12)62336-2

Cited by 28 publications

(9 citation statements)

References 66 publications

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“…Many of these ß-lactamase-stable antibiotics are more expensive than penicillins and primitive cephalosporins. 5,40 For example, in Japan, the costs of cefmetazole, sulbactam/cefoperazone, and imipenem are two to five times as high as the cost of penicillins or primitive cephalosporins. Moreover, to prevent increasing the incidence of resistance to these ß-lactamase-stable agents, they…”

Section: Discussionmentioning

confidence: 99%

Past administration of β-lactam antibiotics and increase in the emergence of β-lactamase–producing bacteria in patients with orofacial odontogenic infections

Kuriyama¹,

Nakagawa²,

Karasawa³

et al. 2000

Oral Surgery, Oral Medicine, Oral Pathology, Oral Radiology, an

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Section: Discussionmentioning

confidence: 99%

Past administration of β-lactam antibiotics and increase in the emergence of β-lactamase–producing bacteria in patients with orofacial odontogenic infections

Kuriyama¹,

Nakagawa²,

Karasawa³

et al. 2000

Oral Surgery, Oral Medicine, Oral Pathology, Oral Radiology, an

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“…12,13 Other concerns about intravenous (as distinct from in¬ travitreal) antibiotics include the cost not only of the drugs, but also of the hospitalization required for their administration. The role of systemic antibiotics in the management of endophthalmitis remains uncertain.…”

Section: Intravenous Antibioticsmentioning

confidence: 99%

The Endophthalmitis Vitrectomy Study

Doft¹

1991

Arch Ophthalmol

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“…While previous reports have established an Arrhenius relationship for the [2+2] cycloaddition between CSI and fluorinated alkenes with respect to temperature changes, 63 we demonstrate this same relationship with TCAI by varying the substrate energetic profile and holding temperature constant. Of the substrates investigated, the tri-O-Troc-protected glycal (7) and benzyl-protected oxidized glycal (9) did not react with TCAI over 5 days of reaction monitoring. The low HOMO energy (−7.330 eV) of 7 is consistent with this observation.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Guidelines for β-Lactam Synthesis: Glycal Protecting Groups Dictate Stereoelectronics and [2+2] Cycloaddition Kinetics

et al. 2020

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The alkene-isocyanate cycloaddition method affords β-lactams from glycals with high regio- and stereoselectivity, but the factors that determine substrate reactivity are poorly understood. Thus, we synthesized a library of 17 electron-rich alkenes (glycals) with varied protecting groups to systematically elucidate the factors that influence their reactivity toward the electron-poor trichloroacetyl isocyanate. The experimentally determined reaction rates exponentially correlate with the computationally determined highest occupied molecular orbital–lowest unoccupied molecular orbital (HOMO–LUMO) gap and natural bond orbital (NBO) valence energies. The electron-withdrawing ability of the protecting groups, but not bulk, impacts the electron density of the glycal allyloxocarbenium system when oriented pseudo-axially (i.e., stereoelectronics). In this conformation, ring σC–O* orbitals oriented antiperiplanar to the allyloxocarbenium system decrease glycal reactivity via negative hyperconjugation as protecting group electron withdrawal increases. Transition-state calculations reveal that protecting group stereoelectronics direct the reaction to proceed via an asynchronous one-step mechanism through a zwitterionic species. The combined experimental and computational findings, along with experimental validation on an unknown glycal, provide insight on the reaction mechanism and the role of distant protecting groups in glycal reactivity. Together, these studies will aid in the synthesis of new β-lactam antibiotics, β-lactamase inhibitors, and bicyclic carbohydrate-β-lactam monomers prepared by the alkene-isocyanate method.

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Cephalosporin, Carbapenem, and Monobactam Antibiotics

Cited by 28 publications

References 66 publications

Past administration of β-lactam antibiotics and increase in the emergence of β-lactamase–producing bacteria in patients with orofacial odontogenic infections

Past administration of β-lactam antibiotics and increase in the emergence of β-lactamase–producing bacteria in patients with orofacial odontogenic infections

The Endophthalmitis Vitrectomy Study

Guidelines for β-Lactam Synthesis: Glycal Protecting Groups Dictate Stereoelectronics and [2+2] Cycloaddition Kinetics

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