Synthesis and biological activity of 13-epi-avermectins: potent anthelmintic agents with an increased margin of safety.
Chemical conversion of the potent anthelmintic natural products avermectin B1 (1) and avermectin B2 (3) to the corresponding 13-epi analogs (15 and 9) is described. The novel analogs retain the full potency of the natural products but are substantially safer.
Blizzard
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TA
Merck Sharp and Dohme Research Laboratories, Rahway, New Jersey 07065.
Margiatto
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GM
Mrozik
H
H
Shoop
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WL
Frankshun
R A
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Fisher
M H
MH
D000818:Animals; D000871:Anthelmintics / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D001156:Artemia; D007559:Ivermectin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology / Q000633:toxicity; D007928:Lethal Dose 50; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D051379:Mice; D012756:Sheep; D013329:Structure-Activity Relationship
D000871:Anthelmintics; D007559:Ivermectin; C019264:avermectin