Synthesis and anthelmintic activity of 13-alkoxymilbemycin derivatives.
The synthesis of milbemycin derivatives having alkyloxy groups at the C-13 position was studied and a series of these analogs of milbemycin A4 and A3 was prepared by the reaction of 13-iodomilbemycin with a variety of alcohols. 13 beta-Phenethyloxy derivatives were found to possess excellent anthelmintic activity. Especially, the activities of derivatives with N-substituted 4-aminophenethyloxy groups were comparable to or superior to ivermectin against Nippostrongylus brasiliensis in rats.
Saito
A
A
Medicinal Chemistry Research Lab., Sankyo Co., Ltd., Tokyo, Japan.
Naito
S
S
Kobayashi
M
M
Tsuchiya
M
M
Toyama
T
T
Kaneko
S
S
Nanba
T
T
Morisawa
Y
Y
D000818:Animals; D000871:Anthelmintics / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D018942:Macrolides; D009559:Nippostrongylus / Q000187:drug effects; D051381:Rats; D017208:Rats, Wistar; D017206:Strongylida Infections / Q000188:drug therapy*; D013329:Structure-Activity Relationship
D000871:Anthelmintics; D000900:Anti-Bacterial Agents; D018942:Macrolides; C027837:moxidectin