Synthesis and biological activity of 13-epi-avermectins: potent anthelmintic agents with an increased margin of safety

T A Blizzard; G M Margiatto; H Mrozik; W L Shoop; R A Frankshun; M H Fisher

doi:10.1021/jm00099a014

Synthesis and biological activity of 13-epi-avermectins: potent anthelmintic agents with an increased margin of safety

J Med Chem. 1992 Oct 16;35(21):3873-8. doi: 10.1021/jm00099a014.

Authors

T A Blizzard¹, G M Margiatto, H Mrozik, W L Shoop, R A Frankshun, M H Fisher

Affiliation

¹ Merck Sharp and Dohme Research Laboratories, Rahway, New Jersey 07065.

PMID: 1433196
DOI: 10.1021/jm00099a014

Abstract

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.

MeSH terms

Animals
Anthelmintics / chemical synthesis*
Anthelmintics / pharmacology
Anthelmintics / toxicity
Artemia
Ivermectin / analogs & derivatives*
Ivermectin / chemical synthesis
Ivermectin / pharmacology
Ivermectin / toxicity
Lethal Dose 50
Magnetic Resonance Spectroscopy
Male
Mice
Sheep
Structure-Activity Relationship

Substances

Anthelmintics
Ivermectin
avermectin