Cladinose analogues of sixteen-membered macrolide antibiotics. I. Synthesis of 4-O-alkyl-L-cladinose analogues via glycosylation.
The synthesis and biological evaluation of sixteen-membered macrolides possessing a 4-O-alkyl-alpha-L-cladinosyl moiety as the neutral sugar are described. The nine novel derivatives have been synthesized by glycosylation with 1-thio sugars. The most active derivative of them showed prolonged antibacterial activity in rat plasma in vitro and improved pharmacokinetics.
Kurihara
K
K
Pharmaceutical Research Center, Meiji Seika Kaisha, Ltd., Yokohama, Japan.
Ajito
K
K
Shibahara
S
S
Ishizuka
T
T
Hara
O
O
Araake
M
M
Omoto
S
S
D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000493:pharmacokinetics / Q000494:pharmacology; D006031:Glycosylation; D006601:Hexoses / Q000737:chemistry*; D007933:Leucomycins / Q000097:blood / Q000652:urine; D008297:Male; D051379:Mice; D008826:Microbial Sensitivity Tests; D051381:Rats; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D006601:Hexoses; D007933:Leucomycins; C013889:cladinose; C026483:midecamycin