GABA receptor antagonists and insecticides: common structural features of 4-alkyl-1-phenylpyrazoles and 4-alkyl-1-phenyltrioxabicyclooctanes

RE Sammelson, P Caboni, KA Durkin…

Index: Sammelson, Robert E.; Caboni, Pierluigi; Durkin, Kathleen A.; Casida, John E. Bioorganic and Medicinal Chemistry, 2004 , vol. 12, # 12 p. 3345 - 3355

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Citation Number: 60

Abstract

Fipronil [5-amino-3-cyano-1-(2, 6-dichloro-4-trifluoromethylphenyl)-4- trifluoromethylsulfinylpyrazole] is one of the most important insecticides. Structure–activity studies described here reveal that fipronil retains its very high binding potency at the human β3 and house fly γ-aminobutyric acid (GABA) receptors and toxicity to house flies on replacing the pyrazole trifluoromethylsulfinyl moiety with tert-butyl or isopropyl and the ...