A γ-lactam analogue of the penems possessing antibacterial activity

Baldwin, Jack E.; Freeman, Richard T.; Lowe, Christopher; Schofield, Christopher J.; Lee, Eun

doi:10.1016/s0040-4020(01)89088-8

Cited by 52 publications

(13 citation statements)

References 19 publications

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“…Both lactivicin and phenoxyacetyl-lactivicin are active against clinically isolated penicillin-resistant Streptococcus pneumoniae strains [107]. Recent efforts to [85], 5.2 [86], 5.3 [87], 5.4 [88], 5.5 [89], 5.6 [90], 5.7 [91] and 5.8 [92]). (B) Examples of inactive compounds (5.9 [93,94], 5.10 [93,94], 5.11 [88], 5.12 [95,96], 5.13 [97], 5.14 [98], 5.15 [99] and 5.16 [100]).…”

Section: Lactivicinmentioning

confidence: 99%

The Road to Avibactam: The First Clinically Useful Non-β-Lactam Working Somewhat Like a β-Lactam

et al. 2016

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Avibactam, which is the first non-β-lactam β-lactamase inhibitor to be introduced for clinical use, is a broad-spectrum serine β-lactamase inhibitor with activity against class A, class C, and, some, class D β-lactamases. We provide an overview of efforts, which extend to the period soon after the discovery of the penicillins, to develop clinically useful non-β-lactam compounds as antibacterials, and, subsequently, penicillin-binding protein and β-lactamase inhibitors. Like the β-lactam inhibitors, avibactam works via a mechanism involving covalent modification of a catalytically important nucleophilic serine residue. However, unlike the β-lactam inhibitors, avibactam reacts reversibly with its β-lactamase targets. We discuss chemical factors that may account for the apparently special nature of β-lactams and related compounds as antibacterials and β-lactamase inhibitors, including with respect to resistance. Avenues for future research including non-β-lactam antibacterials acting similarly to β-lactams are discussed.

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Section: Lactivicinmentioning

confidence: 99%

The Road to Avibactam: The First Clinically Useful Non-β-Lactam Working Somewhat Like a β-Lactam

et al. 2016

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“…Scheme 2 Thiazolidinlactams exhibit a higher chemical stability than thiazolidines. [17] Even in boiling water, 2 and 3 resist an epimerisation of C-9a via open-chain structures. They are also stable at pH 1, hydrolysis being observed only Scheme 3 Eur.…”

Section: Synthesis Of the Tetrahydroxyoctahydro-5-oxothiazolo[32-a]amentioning

confidence: 99%

Polyol Peptidomimetics

Geyer¹,

Moser

2000

Eur. J. Org. Chem.

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Keywords: Peptidomimetics / Reverse turn mimetics / Glycomimetics / Heterocycles / Lactams D-Glucurono-3,6-lactone and L-cysteine combine in a highly stereoselective manner to give the 7,5-bicyclic thiazolidinlactam 2. The α-hydroxy group of the D-glucurono-3,6-lactone was exchanged for an amino function (to give 13) and, after condensation with L-cysteine methyl ester, the polyol dipeptide 7 was obtained. Peptide couplings proceed without the need to protect the three secondary hydroxy groups of the seven-membered ring. The amino group of 7 was depro-

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“… 4 Moreover, spiropyrrolidine-oxindole derivatives exhibit promising biological applications prospects based on their reported antibiotic, antidiabetic, anticonvulsant, antiviral, antibacterial, anti-inflammatory, antitubercular, and anticancer activities. 5 In addition to the selectivity behavior, the understanding of the fundamental principles in the polar 32CA reactions has been gradually developed from prolific studies of the interplay between experimental and theoretical aspects, and it still remains a formidable challenge. 6 The steric and electronic effects are two key factors that can impact the regio- and stereoselectivities of these reactions.…”

Section: Introductionmentioning

confidence: 99%

Unprecedented Regio- and Stereoselective Synthesis of Pyrene-Grafted Dispiro[indoline-3,2′-pyrrolidine-3′,3″-indolines]: Expedient Experimental and Theoretical Insights into Polar [3 + 2] Cycloaddition

et al. 2020

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A series of dispiro[indoline-3,2′-pyrrolidine-3′,3″-indolines] was synthesized via a multicomponent polar [3 + 2] cycloaddition (32CA) reaction of isatin derivatives, sarcosine and ( E )-3-(2-oxo-2-(pyren-1-yl)ethylidene)indolin-2-one derivatives. The regio- and stereochemistries of the cycloadducts were established on the basis of one-dimensional (1D) ( 1 H-, 13 C-, 13 C-CRAPT NMR) and two-dimensional (2D) homonuclear and heteronuclear correlation NMR spectrometry experiments ( 1 H– 1 H gDQFCOSY, 13 C– 1 H-HSQCAD, 13 C– 1 H-HMBCAD, 1 H– 1 H-ROESYAD). The molecular mechanism and regio- and stereoselectivities of the cycloaddition (CA) reaction have been investigated utilizing a density functional theory (DFT) method and were thoroughly explained based on the transition-state stabilities and global/local electrophilicity/nucleophilicity reactivity indices of the reactants.

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A γ-lactam analogue of the penems possessing antibacterial activity

Cited by 52 publications

References 19 publications

The Road to Avibactam: The First Clinically Useful Non-β-Lactam Working Somewhat Like a β-Lactam

The Road to Avibactam: The First Clinically Useful Non-β-Lactam Working Somewhat Like a β-Lactam

Polyol Peptidomimetics

Unprecedented Regio- and Stereoselective Synthesis of Pyrene-Grafted Dispiro[indoline-3,2′-pyrrolidine-3′,3″-indolines]: Expedient Experimental and Theoretical Insights into Polar [3 + 2] Cycloaddition

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