Synthesis of two and antibacterial activity of one novel oxime ether derivatives of erythromycin A

Döndaş, H. Ali; Yaktubay, Naciye

doi:10.1016/s0014-827x(03)00194-0

Cited by 3 publications

(1 citation statement)

References 23 publications

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“…Hence, Dondas H.A. [10] designed erythromycin A 9-O-(2-ethenesulfony-ethyl)-oxime (10a) and erythromycin A 9-O-(3-oxo-butyl)-oxime (10b) from erythromycin A by Michael reaction. The two compounds were found to be active in some cases against C. diphtheriae, manifesting that the transformation of the ketone at C-9 position of erythromycin A to an oxime resulted in a decrease of in vitro antibacterial activity, but the drop in activity was not so dramatic except for S. faecalis and E. coli.…”

Section: -O-substituented Derivativesmentioning

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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Section: -O-substituented Derivativesmentioning

confidence: 99%

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

2010

MRMC

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Synthesis of Two and Antibacterial Activity of One Novel Oxime Ether Derivatives of Erythromycin A.

Döndaş

Yaktubay

2004

ChemInform

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Structure-Activity Relationships and Mechanism of Action of Macrolides Derived from Erythromycin as Antibacterial Agents

Liang

Han

2013

CTMC

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Enormous efforts were focused on the 3-descladinosyl erythromycin derivatives which led to 3-keto (ketolides), 3-O-acyl (acylides), 3-O-carbamate (carbamolides), and 3-O-alkyl (alkylides) and cladinosyl-containing erythromycin derivatives such as 4"-O-acyl, 4"-O-carbamate, and 4"-O-alkyl derivatives as recently exemplified by macrolones (macrolide-quinolone hybrids). Ketolides acquire activity against MLSB-resistant pathogens via a featured arylalkyl extension suspended on the macrolide core, which interacts with a base pair formed by A752Ec and U2609Ec located in the nascent peptide release tunnel of the bacterial rRNA. A base pair formed by C2610Ec and G2505Ec probably is another novel binding site for 3-descladinosyl non-ketolides. It is believed that 4"-derived compounds perhaps interfere with the formation of polypeptide because the extension oriented into peptidyl transferase center (PTC) region. Although macrolones are hybrids of macrolides and quinolones, they do not have dual modes of action, and serve only as protein synthesis inhibitors.

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Synthesis of two and antibacterial activity of one novel oxime ether derivatives of erythromycin A

Cited by 3 publications

References 23 publications

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

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

Synthesis of Two and Antibacterial Activity of One Novel Oxime Ether Derivatives of Erythromycin A.

Structure-Activity Relationships and Mechanism of Action of Macrolides Derived from Erythromycin as Antibacterial Agents

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