CHEMICAL MODIFICATION OF ERYTHROMYCINS: V. SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF 4''-O-METHYL DERIVATIVES OF ERYTHROMYCIN A 11, 12-CYCLIC CARBONATE

Erythromycin A (1) is a macrolide antibiotic used for treatment of infections caused by Gram-positive bacteria and Mycoplasma sp. Its 11,12-cyclic carbonate derivative (2), formed by reaction of 1 with ethylene carbonate, has greater antibacterial activity than 1. While 1 and 2 induced strongly macr...

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Bibliographic Details
Published in:Journal of antibiotics 1990/05/25, Vol.43(5), pp.566-569
Main Authors: MORIMOTO, SHIGEO, MISAWA, YOKO, KONDOH, HIDEAKI, 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 Resistance, Microbial
Erythromycin - analogs & derivatives
Erythromycin - metabolism
Erythromycin - pharmacology
Magnetic Resonance Spectroscopy
Medical sciences
Methylation
Mice
Molecular Conformation
Molecular Structure
Pharmacology. Drug treatments
Staphylococcus - drug effects
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Summary:Erythromycin A (1) is a macrolide antibiotic used for treatment of infections caused by Gram-positive bacteria and Mycoplasma sp. Its 11,12-cyclic carbonate derivative (2), formed by reaction of 1 with ethylene carbonate, has greater antibacterial activity than 1. While 1 and 2 induced strongly macrolide-resistance in Staphylococcus aureus , introduction of an acetyl or some sulfonyl groups at the C-4" position of 1 or 2 resulted in a decrease of inducer activity. On the other hand, it has been reported that 4"-deoxy derivatives of 1 exhibited no difference with 1 in the inducibility test. Consequently, we undertook the methylation of the 4"-hydroxyl group. Herein we report the synthesis and antibacterial activity of 4"-O-methyl derivatives of erythromycin A 11,12-cyclic carbonate.
ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.43.566