Synthesis and antibacterial activities of novel 12-O-methylerythromycin A derivatives.
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).
Ku
Y Y
YY
Chemical Process Research, Pharmaceutical Products Division, Abbott Laboratories, North Chicago, IL 60064-4000, USA.
Riley
D
D
Grieme
T
T
Nilius
A
A
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
C402695:12-O-methylerythromycin A; C402694:9-dihydro-12-O-methylerythromycin A; D000900:Anti-Bacterial Agents; C066550:9-dihydroclarithromycin; D004917:Erythromycin; D017291:Clarithromycin