The synthesis and biological evaluation of some novel aminoheterocyclic methoxime monobactam derivatives.

Wheeler, William J.; Finley, Don R.; Ott, J. L.

doi:10.7164/antibiotics.39.1611

Cited by 3 publications

(3 citation statements)

References 10 publications

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“…Using some novel aminoheterocyclic methoxyimino‐linked cephalosporins as an example, Wheeler et al . undertook the synthesis of aminooxazolyl‐ and aminooxadiazolylmethoxime‐substituted monobactams with the purpose of achieving a more balanced antibacterial spectrum . Although their two derivatives 25a,b turned out to be less active than the aminothiazole analogue 26 and aztreonam 5 (Table ) against a wide variety of aerobic Gram‐negative bacteria, compound 25a was found to be more active than either the aminothiazole derivative 26 or aztreonam 5 against Streptococci (MICs of 1–2 μg/mL compared to 2–64 μg/mL) (Fig.…”

Section: Monobactamsmentioning

confidence: 99%

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Antibacterial and β‐Lactamase Inhibitory Activity of Monocyclic β‐Lactams

Decuyper

Jukič

Sosič

et al. 2017

Medicinal Research Reviews

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Due to the widespread emergence of resistant bacterial strains, an urgent need for the development of new antibacterial agents with novel modes of action has emerged. The discovery of naturally occurring monocyclic β-lactams in the late 1970s, mainly active against aerobic Gram-negative bacteria, has introduced a new approach in the design and development of novel antibacterial β-lactam agents. The main goal was the derivatization of the azetidin-2-one core in order to improve their antibacterial potency, broaden their spectrum of activity, and enhance their β-lactamase stability. In that respect, our review covers the updates in the field of monocyclic β-lactam antibiotics during the last three decades, taking into account an extensive collection of references. An overview of the relationships between the structural features of these monocyclic β-lactams, classified according to their N-substituent, and the associated antibacterial or β-lactamase inhibitory activities is provided. The different paragraphs disclose a number of well-established classes of compounds, such as monobactams, monosulfactams, monocarbams, monophosphams, nocardicins, as well as other known representative classes. Moreover, this review draws attention to some less common but, nevertheless, possibly important types of monocyclic β-lactams and concludes by highlighting the recent developments on siderophore-conjugated classes of monocyclic β-lactams.

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Section: Monobactamsmentioning

confidence: 99%

“…Similar to Wheeler et al ., other research groups tried to replace the 2‐aminothiazole group composed of the 3‐acylamino side chain of numerous monocyclic β‐lactams with other heterocyclic analogues. By acylation of 3‐aminomonobactamic acid derivatives with several isoxazoleacetic and isoxazolecarboxylic acids, Nagy et al .…”

Section: Monobactamsmentioning

confidence: 99%

Antibacterial and β‐Lactamase Inhibitory Activity of Monocyclic β‐Lactams

Decuyper

Jukič

Sosič

et al. 2017

Medicinal Research Reviews

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“…The N -hydroxy-containing compounds, such as 1-hydroxybenzotriazole (HOBt·H 2 O), 1-hydroxy-7-azabenzotriazole (HOAt), and 1-hydroxysuccinimide (HOSu), are widely used as activating reagents in combination with N , N ′-dicyclohexylcarbodiimide (DCC) or N -ethyl- N ′-(3-dimethylaminopropyl)carbodiimide (EDC, WSC) for the construction of an amide bond during the synthesis of peptide and β-lactam antibiotics . Moreover, activated esters by these N -hydroxy-containing compounds have also been employed in the formation of a C(O)−C bond during the preparation of the antibiotic malonomicin .…”

Section: Introductionmentioning

confidence: 99%

Reactions of Monoaryl-Substituted Methylenecyclobutanes and Methylenecyclopropanes with 1-Hydroxybenzotriazole (HOBt), 1-Hydroxy-7-azabenzotriazole (HOAt), and 1-Hydroxysuccinimide (HOSu)

Jiang

Shi

2009

J. Org. Chem.

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Monoaryl-substituted methylenecyclobutanes (MCBs) and methylenecyclopropanes (MCPs) react with 1-hydroxybenzotriazole (HOBt), 1-hydroxy-7-azabenzotriazole (HOAt), and 1-hydroxysuccinimide (HOSu) smoothly to produce the corresponding cyclobutylmethanone and cyclopropylmethanone derivatives 2, 4, and 5 via a cascade epoxidation and nucleophilic addition process or the corresponding epoxides 6 in moderate to good yields under mild conditions. A plausible mechanism has been proposed on the basis of the control experiments and the isolation of the reaction intermediates.

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Synthesis and antibacterial evaluation against resistant Gram-negative bacteria of monobactams bearing various substituents on oxime residue

Lü

Wang

et al. 2020

Bioorganic Chemistry

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The synthesis and biological evaluation of some novel aminoheterocyclic methoxime monobactam derivatives.

Cited by 3 publications

References 10 publications

Antibacterial and β‐Lactamase Inhibitory Activity of Monocyclic β‐Lactams

Antibacterial and β‐Lactamase Inhibitory Activity of Monocyclic β‐Lactams

Reactions of Monoaryl-Substituted Methylenecyclobutanes and Methylenecyclopropanes with 1-Hydroxybenzotriazole (HOBt), 1-Hydroxy-7-azabenzotriazole (HOAt), and 1-Hydroxysuccinimide (HOSu)

Synthesis and antibacterial evaluation against resistant Gram-negative bacteria of monobactams bearing various substituents on oxime residue

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