title: Milbemycin derivatives: modification at the C-5 position.
abstract: Protection of the hydroxyl group at the C-5 position of milbemycin A4 and D was carried out to investigate the influence of the C-5 hydroxyl group on the anthelmintic potency of these derivatives. Moreover, the hydroxyl group was converted into amide groups as bioisosters. Biological activities of these derivatives were measured against Nippostrongylus brasiliensis in vitro, and minimal concentrations which induce 100% immotility in worms were determined for each derivative. Biological testing revealed that the hydroxyl group at C-5 is a structural requirement for retaining anthelmintic activity.
authors.affiliation: Medicinal Chemistry Research Laboratories, Sankyo Co., Ltd., Tokyo, Japan.
authors.forename: S
authors.initials: S
authors.lastname: Naito
authors.forename: T
authors.initials: T
authors.lastname: Nanba
authors.forename: Y
authors.initials: Y
authors.lastname: Owatari
authors.forename: Y
authors.initials: Y
authors.lastname: Nakada
authors.forename: S
authors.initials: S
authors.lastname: Muramatsu
authors.forename: J
authors.initials: J
authors.lastname: Ide
mesh_terms: D000818:Animals; D000871:Anthelmintics / Q000138:chemical synthesis / Q000494:pharmacology*; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000494:pharmacology*; D007559:Ivermectin / Q000031:analogs & derivatives / Q000737:chemistry / Q000494:pharmacology; D018942:Macrolides; D009559:Nippostrongylus / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: D000871:Anthelmintics; D000900:Anti-Bacterial Agents; D018942:Macrolides; D007559:Ivermectin; C019264:avermectin; C027837:moxidectin