Synthesis of gem-difluoro-avermectin derivatives: Potent anthelmintic and anticonvulsant agents

Authors
Meinke, PT Shoop, WL Michael, BF Blizzard, TA Dawson, GR Fisher, MH Mrozik, H
Citation
Pt. Meinke et al., Synthesis of gem-difluoro-avermectin derivatives: Potent anthelmintic and anticonvulsant agents, BIOORG MED, 8(24), 1998, pp. 3643-3646
Citations number
20
Categorie Soggetti
Chemistry & Analysis
Journal title
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
ISSN journal
0960894X → ACNP
Volume
8
Issue
24
Year of publication
1998
Pages
3643 - 3646
Database
ISI
SICI code
0960-894X(199812)8:24<3643:SOGDPA>2.0.ZU;2-U
Abstract
A series of gern-difluoro-avermectin derivatives was synthesized from the c orresponding ketones at positions 4 ", 4', 13, and 23 using diethylaminosul fur trifluoride (DAST). These fluorinated avermectins exhibit potent antipa rasitic activity in a new Haemonchus contortus larval assay and are equipot ent to ivermectin. In addition, 23-gem-difluoro-ivermectin displays useful anticonvulsant activity in mouse models. (C) 1998 Elsevier Science Ltd. All rights reserved.