Design, synthesis, and antibacterial activities of novel 3,6-bicyclolide oximes: Length optimization and zero carbon linker oximes

Tang, Datong; Gai, Ying; Polemeropoulos, Alexander; Chen, Zhigang; Wang, Zhe; Or, Yat Sun

doi:10.1016/j.bmcl.2008.07.118

Cited by 31 publications

(10 citation statements)

References 4 publications

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“…The so-called bicyclolides introduce a second heterocycle between the 6 and 11 or 6 and 3 positions (73, 74). The 6, 11-bicyclolide modithromycin (Figure 1) exhibits improved in vitro efficacy against erm + strains of S. pyogenes showing idiosyncratic resistance to telithromycin (75).…”

Section: Structural Basis Of Resistance To Ptc-targeted Antibioticsmentioning

confidence: 99%

The Chemistry of Peptidyltransferase Center-Targeted Antibiotics: Enzymatic Resistance and Approaches to Countering Resistance

McCusker

Fujimori

2011

ACS Chem. Biol.

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The continued ability to treat bacterial infections requires effective antibiotics. The development of new therapeutics is guided by knowledge of the mechanisms of action of and resistance to these antibiotics. Continued efforts to understand and counteract antibiotic resistance mechanisms at a molecular level have the potential to direct development of new therapeutic strategies in addition to providing insight into the underlying biochemical functions impacted by antibiotics. The interaction of antibiotics with the peptidyltransferase center and adjacent exit tunnel within the bacterial ribosome is the predominant mechanism by which antibiotics impede translation, thus stalling growth and proliferation. Resistance enzymes catalyze the chemical modification of the RNA that composes these functional regions, leading to diminished binding of these antibiotics. This review discusses recent advances in the elucidation of chemical mechanisms underlying resistance and driving the development of new antibiotics.

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Section: Structural Basis Of Resistance To Ptc-targeted Antibioticsmentioning

confidence: 99%

The Chemistry of Peptidyltransferase Center-Targeted Antibiotics: Enzymatic Resistance and Approaches to Countering Resistance

McCusker

Fujimori

2011

ACS Chem. Biol.

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“…Similar to the 6,11-bridged bicyclolides, researchers in Enanta adopted convenient oxime formation to introduce the side chains with different tether lengths to the novel 3,6-bridged carbamate core (Scheme 22) [64]. It was disclosed that unlike EDP-420, the optimal linker is the zero-carbon tether.…”

Section: Novel Bicyclolidesmentioning

confidence: 99%

Recent Advances in the Medicinal Chemistry of Novel Erythromycin- Derivatized Antibiotics

Ying¹,

Tang²

2010

CTMC

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Development of novel erythromycin-based antibiotics has been one of the most studied topics in the past three decades. Such tremendous efforts have generated a number of beneficiary drugs such as clarithromycin, azithromycin and telithromycin. However, widespread application of antibiotics in clinical practice has triggered an increasing emergence of bacterial resistance. Therefore, discovery of novel macrolide antibiotics to suppress the resistance is urgent for human healthcare. This review focuses on advances in the area since 2004.

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“…Ground on the 6,11-bicyclolide, an unprecedente series of 3,6-bicyclolide oximes (5) were designed and prepared by Tang [5]. These compounds with linkers of varying lengths to the secondary binding site were tested against a panel of representative respiratory pathogens, including various mac- with erythromycin A, all of 3, 6-bicyclolide oximes (5a-5f) displayded good activities against the susceptible strains (MIC 0.25 μg/mL), the mef-resistant strains (MIC 0.125 μg/mL), and H. influenzae.…”

Section: 6-bicyclolidesmentioning

confidence: 99%

Various Novel Erythromycin Derivatives Obtained by Different Modifications: Recent Advance in Macrolide Antibiotics

2010

MRMC

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The rapid emergence of drug resistance intensified the search for new antimicrobial agents, leading to lots of novel derivatives obtained from 14- and 15-membered macrolides by chemical modifications. Many of them exhibited enhanced antibacterial activity and expanded antibacterial spectrum. Especially some of them were found to be potent for the treatment of multi-drug-resistant bacterial infections. Besides, the other biological effects of macrolide derivatives were also found. In this article, we reviewed the recent advance in the novel macrolide derivatives designed by different structural modifications on erythronolide skeleton, cladinose and desosamine in the structures.

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Design, synthesis, and antibacterial activities of novel 3,6-bicyclolide oximes: Length optimization and zero carbon linker oximes

Cited by 31 publications

References 4 publications

The Chemistry of Peptidyltransferase Center-Targeted Antibiotics: Enzymatic Resistance and Approaches to Countering Resistance

The Chemistry of Peptidyltransferase Center-Targeted Antibiotics: Enzymatic Resistance and Approaches to Countering Resistance

Recent Advances in the Medicinal Chemistry of Novel Erythromycin- Derivatized Antibiotics

Various Novel Erythromycin Derivatives Obtained by Different Modifications: Recent Advance in Macrolide Antibiotics

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