CHEMICAL MODIFICATION OF ERYTHROMYCINS: II. SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF O-ALKYL DERIVATIVES OF ERYTHROMYCIN A

A series of O-alkyl erythromycin A derivatives have been synthesized and their antibacterial activities compared with those of erythromycin A (1) and 6-O-methylerythromycin A (3). Methylation of the hydroxyl groups of erythromycin A analogue proceeded stepwise by the two main pathways beginning at t...

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Bibliographic Details
Published in:Journal of antibiotics 1990/03/25, Vol.43(3), pp.286-294
Main Authors: MORIMOTO, SHIGEO, MISAWA, YOKO, ADACHI, TAKASHI, NAGATE, TAKATOSHI, WATANABE, YOSHIAKI, OMURA, SADAFUMI
Format: Article
Language:English
Subjects:
Animals
Antibacterial agents
Antibiotics. Antiinfectious agents. Antiparasitic agents
Bacteria - drug effects
Biological and medical sciences
Drug Stability
Erythromycin - analogs & derivatives
Erythromycin - metabolism
Erythromycin - pharmacokinetics
Erythromycin - pharmacology
Lung - metabolism
Magnetic Resonance Spectroscopy
Male
Medical sciences
Mice
Mice, Inbred ICR
Molecular Structure
Pharmacology. Drug treatments
Staphylococcal Infections - drug therapy
Tissue Distribution
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Summary:A series of O-alkyl erythromycin A derivatives have been synthesized and their antibacterial activities compared with those of erythromycin A (1) and 6-O-methylerythromycin A (3). Methylation of the hydroxyl groups of erythromycin A analogue proceeded stepwise by the two main pathways beginning at the C-6 and C-11 positions, individually. O-Alkylation, other than methylation, took place at the C-11 hydroxyl group exclusively. Among O-alkyl derivatives, 6, 12-di-O-methylerythromycin A (5) showed comparable in vitro antibacterial activity to those of 1 and 3. 11-O-Methylerythromycin A (8) was slightly less active than 1. O-Methylation at the C-4" position resulted in a decrease of antibacterial activity.
ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.43.286