Synthesis and antibacterial activity of derivatives of 6-O-allylic acylides.
A series of novel acylide derivatives have been synthesized from erythromycin A via a facile procedure. By applying this procedure, cyclic carbonation to C-11,12 position, acylation to C-3 hydroxyl, and deprotection provided the desired acylides. These compounds showed antibacterial activity against both macrolide-susceptible strains and macrolide-resistant strains. Because of existence of 6-O-allyl substitution, these derivatives can be used as intermediates for further structural modification.
Xu
Peng
P
Key Laboratory of Bioactivity Substance and Resources Utilization of Chinese Herbal Medicine, Ministry of Education Institute of Materia Medica, Peking Union Medica College & Chinese Academy of Medical Sciences, Beijing 100050, PR China.
Liu
Lu
L
Jin
Zhiping
Z
Lei
Pingsheng
P
D000215:Acylation; D000475:Alkenes / Q000138:chemical synthesis / Q000494:pharmacology*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D024901:Drug Resistance, Multiple, Bacterial; D004917:Erythromycin / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000494:pharmacology*; D006090:Gram-Negative Bacteria / Q000187:drug effects*; D006094:Gram-Positive Bacteria / Q000187:drug effects*; D018942:Macrolides / Q000138:chemical synthesis / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D008956:Models, Chemical; D013329:Structure-Activity Relationship
D000475:Alkenes; D000900:Anti-Bacterial Agents; D018942:Macrolides; D004917:Erythromycin