An efficient entry to new sugar modified ketolide antibiotics

Romero, Alex; Liang, Chang-Hsing; Chiu, Yu-Hung; Yao, Sulan; Duffield, Jonathan J.; Sucheck, Steven J.; Marby, Ken; Rabuka, David; Leung, Po Yee; Shue, Youe‐Kong; Ichikawa, Yoshi; Hwang, Cheol Kyu

doi:10.1016/j.tetlet.2005.01.023

Cited by 36 publications

(16 citation statements)

References 10 publications

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“…Other structure modifications included the following: modified 5-O-desosamine ketolides (Chen et al, 2012), fluorination at the C2-and/or C12 positions (Denis and Bonnefoy, 2001;Krokidis et al, 2014), variation of the cyclic carbonate and hydrazono-carbamate at 11,12 positions (Hunziker et al, 2004;Andreotti et al, 2007;Zhu et al, 2007) or variation of the aglycon ring (Shaw et al, 2005;Ashley et al, 2006;Sugimoto and Tanikawa, 2010). Lastly, modifications also included replacement of desosamine with different sugars Romero et al, 2005;Chen et al, 2012). A detailed review covering all the chemical efforts to improve the ketolide activity is presented in the review of Liang and Han (2013).…”

Section: Antimicrobial Activity and Chemical Derivatizationmentioning

confidence: 99%

The macrolide antibiotic renaissance

Dinos

2017

British J Pharmacology

305

235

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Macrolides represent a large family of protein synthesis inhibitors of great clinical interest due to their applicability to human medicine. Macrolides are composed of a macrocyclic lactone of different ring sizes, to which one or more deoxy-sugar or amino sugar residues are attached. Macrolides act as antibiotics by binding to bacterial 50S ribosomal subunit and interfering with protein synthesis. The high affinity of macrolides for bacterial ribosomes, together with the highly conserved structure of ribosomes across virtually all of the bacterial species, is consistent with their broad-spectrum activity. Since the discovery of the progenitor macrolide, erythromycin, in 1950, many derivatives have been synthesised, leading to compounds with better bioavailability and acid stability and improved pharmacokinetics. These efforts led to the second generation of macrolides, including well-known members such as azithromycin and clarithromycin. Subsequently, in order to address increasing antibiotic resistance, a third generation of macrolides displaying improved activity against many macrolide resistant strains was developed. However, these improvements were accompanied with serious side effects, leading to disappointment and causing many researchers to stop working on macrolide derivatives, assuming that this procedure had reached the end. In contrast, a recent published breakthrough introduced a new chemical platform for synthesis and discovery of a wide range of diverse macrolide antibiotics. This chemical synthesis revolution, in combination with reduction in the side effects, namely, 'Ketek effects', has led to a macrolide renaissance, increasing the hope for novel and safe therapeutic agents to combat serious human infectious diseases.

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Section: Antimicrobial Activity and Chemical Derivatizationmentioning

confidence: 99%

The macrolide antibiotic renaissance

Dinos

2017

British J Pharmacology

305

235

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“…34,51,52 As CuI has a tetrahedrally coordinated Wurtzite lattice structure, 53 a certain amount of acetylide anion is required before the reactive complex can form. In the absence of the base, elevated temperatures 54,55 or ultrasonication conditions, 56 can allow a CuAAC reaction with CuI catalyst to proceed successfully. Though this reaction was performed at room temperature without any external source of energy like sonication, good cyclization yield was obtained.…”

Section: Effect Of Varying Concentrations Of Piperidine On Peptide Cymentioning

confidence: 99%

Copper–ligand clusters dictate size of cyclized peptide formed during alkyne–azide cycloaddition on solid support

2021

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“…In addition, Optimer carried out studies on modification of desosamine moiety (Scheme 2) [25,26]. The desosamine in intermediate 11 was first removed to expose the 5-hydroxyl group, and then various modified sugars were smoothly installed via a mild glycosylation reaction.…”

Section: Novel Agents With Telithromycin-like Structuresmentioning

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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An efficient entry to new sugar modified ketolide antibiotics

Cited by 36 publications

References 10 publications

The macrolide antibiotic renaissance

The macrolide antibiotic renaissance

Copper–ligand clusters dictate size of cyclized peptide formed during alkyne–azide cycloaddition on solid support

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

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