New Classes of Antibacterial Oxazolidinones with C‐5, Methylene O‐Linked Heterocyclic Side Chains.

Gravestock, Michael B.; Acton, David; Betts, Michael J.; Dennis, Michael Robert; Hatter, Glenn; McGregor, Alexandra; Swain, Michael L.; Wilson, R. Geoffrey; Woods, Lisa; Wookey, Alan

doi:10.1002/chin.200413094

Cited by 2 publications

(2 citation statements)

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“…The history of the discovery and development of the oxazolidinone class as antibacterial agents have been previously reviewed, [79][80][81] as well as early SAR studies. [82][83][84][85][86][87][88][89][90][91][92][93][94] Oxazolidinones exert their antibacterial activity by binding to the bacterial 70S ribosome and inhibiting protein synthesis. The mechanism of this effect is unique from other classes of protein synthesis inhibitors in that they bind to the 50S ribosomal subunit, thereby preventing the binding of aminoacyl-tRNA to the peptidyl transferase center at the Asite.…”

Section: Next-generation Oxazolidinone Antibacterialsmentioning

confidence: 99%

Recent advances in the rational design and optimization of antibacterial agents

et al. 2016

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This review discusses next-generation antibacterial agents developed using rational, or targeted, drug design strategies. The focus of this review is on small-molecule compounds that have been designed to bypass developing bacterial resistance, improve the antibacterial spectrum of activity, and/or to optimize other properties, including physicochemical and pharmacokinetic properties. Agents are discussed that affect known antibacterial targets, such as the bacterial ribosome, nucleic acid binding proteins, and proteins involved in cell-wall biosynthesis; as well as some affecting novel bacterial targets which do not have currently marketed agents. The discussion of the agents focuses on the rational design strategies employed and the synthetic medicinal chemistry and structure-based design techniques utilized by the scientists involved in the discoveries, including such methods as ligand- and structure-based strategies, structure-activity relationship (SAR) expansion strategies, and novel synthetic organic chemistry methods. As such, the discussion is limited to small-molecule therapeutics that have confirmed macromolecular targets and encompasses only a fraction of all antibacterial agents recently approved or in late-stage clinical trials. The antibacterial agents selected have been recently approved for use on the U.S. or European markets or have shown promising results in phase 2 or phase 3 U.S. clinical trials.

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Section: Next-generation Oxazolidinone Antibacterialsmentioning

confidence: 99%

Recent advances in the rational design and optimization of antibacterial agents

et al. 2016

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“…Meanwhile, further modifications of the new skeleton compound were carried out at C-5 side chain, as the reported structural modifications of oxazolidinone compounds were mainly concentrated in the C-5 side chain and the C-ring unit (30)(31)(32)(33)(34) to optimize their biological activities. It has been reported that the introduction of acetamide group (3,35,36) or triazole group (37)(38)(39)(40) at the C-5 position in oxazolidinone compounds shows good antibacterial activities; thus, acetamide group or triazole group were chosen for the derivatization of C-5 side chain. Additionally, a growing body of evidence suggests that the introduction of halogen group in the antibacterial agents could improve their biological activities (41); thus, F atom and Cl atom were introduced to some designed compound.…”

Section: Design Of Compoundsmentioning

confidence: 99%

Novel Oxazolidinone Antibacterial Analogues with a Substituted Ligustrazine C‐ring Unit

et al. 2015

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A series of novel oxazolidinone compounds with a substituted ligustrazine C-ring unit and different substituted groups at the C-5 side chain were designed and synthesized using linezolid as a lead and based on a scaffold hopping strategy. Their antibacterial and anti-inflammatory activities were evaluated. The results of in vitro antibacterial assays showed that all fourteen target compounds displayed potent activity against Gram-positive pathogens, particularly 8b, 13b, 14a, 14b, 15a, and 15b. Moreover, 14a and 14b exhibited significant inhibitory activities on the production of inflammatory mediators, including nitric oxide, interleukin-6, and tumor necrosis factor-alpha. Thus, these derivatives could serve as valuable candidates to develop anti-infective agents for the treatment of chronic wounds.

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New Classes of Antibacterial Oxazolidinones with C‐5, Methylene O‐Linked Heterocyclic Side Chains.

Cited by 2 publications

References 1 publication

Recent advances in the rational design and optimization of antibacterial agents

Recent advances in the rational design and optimization of antibacterial agents

Novel Oxazolidinone Antibacterial Analogues with a Substituted Ligustrazine C‐ring Unit

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