Chemical modification of erythromycins. IV. Synthesis and biological properties of 6-O-methylerythromycin B.
6-O-Methylerythromycin B has been synthesized from erythromycin B via regioselective methylation of the 6-hydroxyl group in 71% overall yield. This compound shows in vitro antibacterial activity comparable to erythromycins A and B and exhibits superior in vivo activity with improved pharmacokinetic properties.
Morimoto
S
S
Research Center, Taisho Pharmaceutical Co., Ltd., Saitama, Japan.
Adachi
T
T
Misawa
Y
Y
Nagate
T
T
Watanabe
Y
Y
Omura
S
S
D000818:Animals; D001419:Bacteria / Q000187:drug effects*; D055598:Chemical Phenomena; D002621:Chemistry; D004917:Erythromycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000493:pharmacokinetics / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008745:Methylation; D015394:Molecular Structure; D051381:Rats
D004917:Erythromycin; C064663:6-O-methylerythromycin B; C064662:berythromycin