Substituted-amidine derivatives of diazabicyclooctane as prospective β-lactamase inhibitors

Liu, Yuanbai; Ji, Jingwen; Sun, Jian; He, Lili; Gao, Yuanyu; Zhai, Lijuan; Ji, Jinbo; Ma, Xueqin; Mu, Yangxiu; Tang, Dong; Yang, Haikang; Iqbal, Zafar; Yang, Zhixiang

doi:10.1007/s00706-021-02888-3

Cited by 4 publications

(2 citation statements)

References 27 publications

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“…Amidine substituted DBOs: Our group synthesized the amidine derivative of avibactam by replacing its amide group at the C2 of the DBO ring. The amidine-substituted derivative was further modified by reacting the NH 2 group of the amidine moiety with numerous functionalities [82][83][84][85][86][87]. Amidine derivatives 79 and 82 were the key intermediates for the synthesis of the target compounds.…”

Section: Fused Pyrazole Dbos and Etx0462mentioning

confidence: 99%

Recent Developments to Cope the Antibacterial Resistance via β-Lactamase Inhibition

et al. 2022

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Antibacterial resistance towards the β-lactam (BL) drugs is now ubiquitous, and there is a major global health concern associated with the emergence of new β-lactamases (BLAs) as the primary cause of resistance. In addition to the development of new antibacterial drugs, β-lactamase inhibition is an alternative modality that can be implemented to tackle this resistance channel. This strategy has successfully revitalized the efficacy of a number of otherwise obsolete BLs since the discovery of the first β-lactamase inhibitor (BLI), clavulanic acid. Over the years, β-lactamase inhibition research has grown, leading to the introduction of new synthetic inhibitors, and a few are currently in clinical trials. Of note, the 1, 6-diazabicyclo [3,2,1]octan-7-one (DBO) scaffold gained the attention of researchers around the world, which finally culminated in the approval of two BLIs, avibactam and relebactam, which can successfully inhibit Ambler class A, C, and D β-lactamases. Boronic acids have shown promise in coping with Ambler class B β-lactamases in recent research, in addition to classes A, C, and D with the clinical use of vaborbactam. This review focuses on the further developments in the synthetic strategies using DBO as well as boronic acid derivatives. In addition, various other potential serine- and metallo- β-lactamases inhibitors that have been developed in last few years are discussed briefly as well. Furthermore, binding interactions of the representative inhibitors have been discussed based on the crystal structure data of inhibitor-enzyme complex, published in the literature.

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Section: Fused Pyrazole Dbos and Etx0462mentioning

confidence: 99%

Recent Developments to Cope the Antibacterial Resistance via β-Lactamase Inhibition

et al. 2022

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“…Chiral β-lactams, an important class of heterocyclic compounds, are present in a wide range of natural products and pharmaceutical molecules. − Among them, chiral α-amino-β-lactams with pronounced biological activities have attracted the interest of synthetic organic chemists. − Notable examples of these chiral α-amino-β-lactams have attractive antibacterial activities, such as penicilliums, nocardicins, and sulfazecin (Scheme A). As a result, a variety of synthetic strategies have been elegantly developed for the construction of chiral α-amino-β-lactams. ,− Among them, the most popular strategy is the asymmetric Staudinger [2 + 2] cycloaddition, which has been successfully applied to the synthesis of antibiotic precursors containing chiral α-amino-β-lactams, such as loracarbef and Gram-negative strains (Scheme B, left). However, traditional approaches generally rely on the utilization of chiral auxiliaries.…”

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Copper-Catalyzed Enantioconvergent Radical C(sp³)–N Cross-Coupling to Access Chiral α-Amino-β-lactams

Zheng,

Liu,

et al. 2023

Precision Chemistry

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A copper-catalyzed enantioconvergent radical C-(sp 3 )−N cross-coupling of racemic tertiary α-bromo-β-lactams with aromatic amines is developed under mild thermal reaction conditions. The use of a sterically demanded oxazoline-derived sulfonamide N,N,N-ligand is crucial for the reaction initiation and effective enantio-discrimination of the azetidinone-derived cyclic alkyl radicals. The strategy provides an attractive approach to access chiral α-amino-β-lactams, an important structural motif in many biologically active molecules. Preliminary mechanistic studies support the formation of azetidinone-derived alkyl radicals from the L*Cu(I)-amido complex and α-bromo-β-lactams.

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Synergistic Antibacterial Activity of Meropenem and Imipenem in Combination with Diazabicyclooctane Derivatives

Sun

He²,

Ji³

et al. 2022

Russ J Gen Chem

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Substituted-amidine derivatives of diazabicyclooctane as prospective β-lactamase inhibitors

Cited by 4 publications

References 27 publications

Recent Developments to Cope the Antibacterial Resistance via β-Lactamase Inhibition

Recent Developments to Cope the Antibacterial Resistance via β-Lactamase Inhibition

Copper-Catalyzed Enantioconvergent Radical C(sp³)–N Cross-Coupling to Access Chiral α-Amino-β-lactams

Synergistic Antibacterial Activity of Meropenem and Imipenem in Combination with Diazabicyclooctane Derivatives

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Substituted-amidine derivatives of diazabicyclooctane as prospective β-lactamase inhibitors

Cited by 4 publications

References 27 publications

Recent Developments to Cope the Antibacterial Resistance via β-Lactamase Inhibition

Recent Developments to Cope the Antibacterial Resistance via β-Lactamase Inhibition

Copper-Catalyzed Enantioconvergent Radical C(sp3)–N Cross-Coupling to Access Chiral α-Amino-β-lactams

Synergistic Antibacterial Activity of Meropenem and Imipenem in Combination with Diazabicyclooctane Derivatives

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Copper-Catalyzed Enantioconvergent Radical C(sp³)–N Cross-Coupling to Access Chiral α-Amino-β-lactams