Synthesis and antibacterial activity of the tricyclic ketolides TE-802 and its analogs.

Abstract

The novel 6-O-methyl tricyclic ketolides TE-802 and its analogs were synthesized by two successive cyclization reactions, 11,12-cyclic carbamate formation by intramolecular Michael addition and 9,11-diazaheptene ring construction by intramolecular dehydration reaction. These new tricyclic ketolides exhibited good in vitro antibacterial activity against not only erythromycin-susceptible strains but also erythromycin-resistant Staphylococcus aureus and Streptococcus pneumoniae, which are problematic pathogens of nosocomial and community-acquired respiratory tract infections, respectively.

• Authors: M Kashimura, T Asaka, Y Misawa, K Matsumoto, S Morimoto
• Journal: The Journal of antibiotics (J Antibiot (Tokyo)) Vol. 54 Issue 8 Pg. 664-78 (Aug 2001) ISSN: 0021-8820 [Print] England
• PMID: 11592503 (Publication Type: Journal Article)

Chemical References

• Anti-Bacterial Agents
• Ketolides
• Macrolides
• TE-802
• Erythromycin

Topics

• Anti-Bacterial Agents (chemical synthesis, chemistry, pharmacology)
• Cyclization
• Drug Resistance, Microbial
• Erythromycin (pharmacology)
• Ketolides
• Macrolides
• Magnetic Resonance Spectroscopy
• Molecular Structure
• Staphylococcus aureus (drug effects)
• Structure-Activity Relationship