title: Synthesis and antibacterial activities of novel 12-O-methylerythromycin A derivatives.
abstract: The novel erythromycin A derivatives: 9(S)-9-dihydro-12-O-methylerythromycin A (6) and 12-O-methyerythromycin A (3), have been prepared using a new synthetic approach. The critical step is the regioselective methylation of the 12-hydroxyl of the boron complex of 2',4"-O-bis(trimethylsilyl)-9(S)-9-dihydroerythromycin A (8), which has unprotected 6-, 9- and 11-hydroxyl groups. The antibacterial activities of these new derivatives were compared with those of erythromycin A (1), clarithromycin (2) and 9(S)-9-dihydroclarithromycin (5).
authors.affiliation: Chemical Process Research, Pharmaceutical Products Division, Abbott Laboratories, North Chicago, IL 60064-4000, USA.
authors.forename: Y Y
authors.initials: YY
authors.lastname: Ku
authors.forename: D
authors.initials: D
authors.lastname: Riley
authors.forename: T
authors.initials: T
authors.lastname: Grieme
authors.forename: A
authors.initials: A
authors.lastname: Nilius
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D017291:Clarithromycin / Q000494:pharmacology*; D004917:Erythromycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology / Q000627:therapeutic use; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D013329:Structure-Activity Relationship
chemical_list: C402695:12-O-methylerythromycin A; C402694:9-dihydro-12-O-methylerythromycin A; D000900:Anti-Bacterial Agents; C066550:9-dihydroclarithromycin; D004917:Erythromycin; D017291:Clarithromycin