title: Cladinose analogues of sixteen-membered macrolide antibiotics. I. Synthesis of 4-O-alkyl-L-cladinose analogues via glycosylation.
abstract: 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.
authors.affiliation: Pharmaceutical Research Center, Meiji Seika Kaisha, Ltd., Yokohama, Japan.
authors.forename: K
authors.initials: K
authors.lastname: Kurihara
authors.forename: K
authors.initials: K
authors.lastname: Ajito
authors.forename: S
authors.initials: S
authors.lastname: Shibahara
authors.forename: T
authors.initials: T
authors.lastname: Ishizuka
authors.forename: O
authors.initials: O
authors.lastname: Hara
authors.forename: M
authors.initials: M
authors.lastname: Araake
authors.forename: S
authors.initials: S
authors.lastname: Omoto
mesh_terms: 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
chemical_list: D000900:Anti-Bacterial Agents; D006601:Hexoses; D007933:Leucomycins; C013889:cladinose; C026483:midecamycin